MiMeDB: Showing metabocard for 5,10-Methenyltetrahydrofolic acid (MMDBc0031998)

Microbial

Human

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:58:02 UTC

Update Date

2025-11-05 17:13:01 UTC

Metabolite ID

MMDBc0031998

Metabolite Identification

Common Name

5,10-Methenyltetrahydrofolic acid

Description

5,10-Methenyltetrahydrofolic acid is a member of the folate class of compounds, specifically a derivative of tetrahydrofolate. This metabolite plays a crucial role in various biochemical pathways, particularly in one-carbon metabolism and nucleotide synthesis. Chemically, it features a methenyl group at the 5 and 10 positions of the tetrahydrofolate structure, which is essential for its function as a coenzyme in the transfer of one-carbon units. The biosynthesis of 5,10-methenyltetrahydrofolic acid polyglutamates is facilitated by the bifunctional dihydrofolate synthase/folylpolyglutamate synthase type 2 (folC2) gene, which is vital for the suppression of TNF production by activated human monocytes (PMID:27353144 ). Additionally, it has been shown that UV radiation does not affect the formylation of tetrahydrofolate, leading to the formation of 5,10-methenyltetrahydrofolic acid and its conversion to 5-formyltetrahydrofolic acid (PMID:20586292 ). Furthermore, this compound has been observed to enhance photolyase activity in enzyme reactions (PMID:15158485 ), indicating its potential involvement in photobiological processes.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

644350
  Mrv1652309042000212D          

 34 37  0  0  1  0            999 V2000
    1.9058    0.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433    1.1950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808   -2.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2059    0.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1626    1.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -1.6629    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.2059   -0.9484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0831    1.8659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1806    0.1786    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.9184   -0.2339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096   -0.6464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3603    0.5967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6227    1.8857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808   -0.9484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9683   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1806   -0.6464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3999   -0.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8951   -1.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7308    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -1.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3999    0.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3669    1.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096    0.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8818    1.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8951    0.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0934   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4434   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6809    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6809   -0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8559    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8559   -0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1108   -1.3027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 20  2  0  0  0  0
  3 21  2  0  0  0  0
  4 22  2  0  0  0  0
  5 26  2  0  0  0  0
  6 21  1  0  0  0  0
 14  7  1  6  0  0  0
  7 22  1  0  0  0  0
  8 24  1  0  0  0  0
  9 17  1  0  0  0  0
  9 23  2  0  0  0  0
  9 27  1  0  0  0  0
 10 18  1  0  0  0  0
 10 23  1  0  0  0  0
 10 28  1  0  0  0  0
 11 19  1  0  0  0  0
 11 25  1  0  0  0  0
 12 24  1  0  0  0  0
 12 25  1  0  0  0  0
 13 24  2  0  0  0  0
 13 26  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 34  1  1  0  0  0
 22 29  1  0  0  0  0
 25 27  2  0  0  0  0
 26 27  1  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 29 32  2  0  0  0  0
 29 33  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  CHG  2   6  -1   9   1
M  END

HMDB0001354
     RDKit          3D
5,10-Methenyltetrahydrofolic acid
 54 57  0  0  0  0  0  0  0  0999 V2000
   -8.8642    1.7349   -1.7321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5520    1.3753   -1.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4659    1.5324   -2.0374 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2076    1.2072   -1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.3619   -2.3754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0426    0.6924   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1500    0.5250    0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3956    0.8683   -0.0338 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9600   -0.0100    1.7067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7011   -0.4744    2.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6437   -0.6293    1.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3018   -0.3055    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5862    0.0731    0.5578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288   -0.1688    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.7731    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494   -1.0054    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987   -0.6380   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8903   -0.8352   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600   -0.6610   -1.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193   -1.2232    0.3313 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2175   -1.4141   -0.0935 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0231   -0.4861    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647    0.9236    0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7564    1.4067   -0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3070    0.7139   -1.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3175    2.6877   -1.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6055   -2.8440    0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3572   -3.1432    1.1225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110   -3.8223   -0.6630 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6597   -0.0234   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351    0.1961   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833    0.7110   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7541    0.3191    0.1216 N   0  0  0  0  0  4  0  0  0  0  0  0
   -9.4205    2.5045   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2683    1.1707   -2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2175    0.7352    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -0.0785    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4044    0.2215    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8544   -1.4799    2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -1.6513    0.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217    0.5863    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -1.1534    2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931   -1.0714    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763   -1.4818    1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392   -1.3677    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3182   -1.2493   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8056   -0.7366    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103   -0.5572    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646    1.0017    0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1412    1.6077    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5262    2.7540   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    0.2754   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.6770   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    1.4212   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 13 32  1  0
 32 33  2  0
  8  2  1  0
 33 11  1  0
 33  6  1  0
 31 14  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 30 52  1  0
 31 53  1  0
 32 54  1  0
M  CHG  2  29  -1  33   1
M  END

644350
  Mrv1652309042000212D          

 34 37  0  0  1  0            999 V2000
    1.9058    0.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433    1.1950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808   -2.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2059    0.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1626    1.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -1.6629    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.2059   -0.9484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0831    1.8659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1806    0.1786    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.9184   -0.2339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096   -0.6464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3603    0.5967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6227    1.8857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808   -0.9484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9683   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1806   -0.6464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3999   -0.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8951   -1.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7308    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -1.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3999    0.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3669    1.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096    0.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8818    1.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8951    0.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0934   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4434   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6809    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6809   -0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8559    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8559   -0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1108   -1.3027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 20  2  0  0  0  0
  3 21  2  0  0  0  0
  4 22  2  0  0  0  0
  5 26  2  0  0  0  0
  6 21  1  0  0  0  0
 14  7  1  6  0  0  0
  7 22  1  0  0  0  0
  8 24  1  0  0  0  0
  9 17  1  0  0  0  0
  9 23  2  0  0  0  0
  9 27  1  0  0  0  0
 10 18  1  0  0  0  0
 10 23  1  0  0  0  0
 10 28  1  0  0  0  0
 11 19  1  0  0  0  0
 11 25  1  0  0  0  0
 12 24  1  0  0  0  0
 12 25  1  0  0  0  0
 13 24  2  0  0  0  0
 13 26  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 34  1  1  0  0  0
 22 29  1  0  0  0  0
 25 27  2  0  0  0  0
 26 27  1  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 29 32  2  0  0  0  0
 29 33  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  CHG  2   6  -1   9   1
M  END
> <DATABASE_ID>
MMDBc0031998

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CN(C=[N+]1C1=C(NC2)NC(N)=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1

> <INCHI_KEY>
MEANFMOQMXYMCT-OLZOCXBDSA-N

> <FORMULA>
C20H21N7O6

> <MOLECULAR_WEIGHT>
455.424

> <EXACT_MASS>
455.155331439

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.38318064408257

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-3.2723940359857626

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.7122602199699957

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.985128746522236

> <JCHEM_PKA_STRONGEST_BASIC>
2.0370736672090084

> <JCHEM_POLAR_SURFACE_AREA>
196.76999999999998

> <JCHEM_REFRACTIVITY>
155.82450000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001354
     RDKit          3D
5,10-Methenyltetrahydrofolic acid
 54 57  0  0  0  0  0  0  0  0999 V2000
   -8.8642    1.7349   -1.7321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5520    1.3753   -1.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4659    1.5324   -2.0374 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2076    1.2072   -1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.3619   -2.3754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0426    0.6924   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1500    0.5250    0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3956    0.8683   -0.0338 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9600   -0.0100    1.7067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7011   -0.4744    2.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6437   -0.6293    1.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3018   -0.3055    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5862    0.0731    0.5578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288   -0.1688    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.7731    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494   -1.0054    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987   -0.6380   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8903   -0.8352   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600   -0.6610   -1.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193   -1.2232    0.3313 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2175   -1.4141   -0.0935 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0231   -0.4861    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647    0.9236    0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7564    1.4067   -0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3070    0.7139   -1.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3175    2.6877   -1.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6055   -2.8440    0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3572   -3.1432    1.1225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110   -3.8223   -0.6630 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6597   -0.0234   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351    0.1961   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833    0.7110   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7541    0.3191    0.1216 N   0  0  0  0  0  4  0  0  0  0  0  0
   -9.4205    2.5045   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2683    1.1707   -2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2175    0.7352    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -0.0785    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4044    0.2215    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8544   -1.4799    2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -1.6513    0.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217    0.5863    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -1.1534    2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931   -1.0714    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763   -1.4818    1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392   -1.3677    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3182   -1.2493   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8056   -0.7366    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103   -0.5572    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646    1.0017    0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1412    1.6077    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5262    2.7540   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    0.2754   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.6770   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    1.4212   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 13 32  1  0
 32 33  2  0
  8  2  1  0
 33 11  1  0
 33  6  1  0
 31 14  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 30 52  1  0
 31 53  1  0
 32 54  1  0
M  CHG  2  29  -1  33   1
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 644350                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0       3.557   0.897   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.867   2.231   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.177  -4.438   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.718   0.897   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      18.970   3.462   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.867  -3.104   0.000  0.00  0.00           O-1
HETATM    7  N   UNK     0       9.718  -1.770   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      24.422   3.483   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      19.004   0.333   0.000  0.00  0.00           N+1
HETATM   10  N   UNK     0      16.648  -0.437   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      21.671  -1.207   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      23.073   1.114   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      21.696   3.520   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       8.177  -1.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.407  -0.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.867  -0.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.004  -1.207   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.546  -1.676   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.338  -1.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.097   0.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.407  -3.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.488  -0.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.546   0.803   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.085   2.718   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.671   0.333   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.313   2.707   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.338   1.103   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.108  -0.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.028  -0.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.338   0.897   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.338  -1.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.798   0.897   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.798  -1.770   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0      18.873  -2.432   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   26                                                            
CONECT    6   21                                                            
CONECT    7   14   22                                                       
CONECT    8   24                                                            
CONECT    9   17   23   27                                                  
CONECT   10   18   23   28                                                  
CONECT   11   19   25                                                       
CONECT   12   24   25                                                       
CONECT   13   24   26                                                       
CONECT   14    7   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   20                                                       
CONECT   17    9   18   19   34                                             
CONECT   18   10   17                                                       
CONECT   19   11   17                                                       
CONECT   20    1    2   16                                                  
CONECT   21    3    6   14                                                  
CONECT   22    4    7   29                                                  
CONECT   23    9   10                                                       
CONECT   24    8   12   13                                                  
CONECT   25   11   12   27                                                  
CONECT   26    5   13   27                                                  
CONECT   27    9   25   26                                                  
CONECT   28   10   30   31                                                  
CONECT   29   22   32   33                                                  
CONECT   30   28   32                                                       
CONECT   31   28   33                                                       
CONECT   32   29   30                                                       
CONECT   33   29   31                                                       
CONECT   34   17                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0001354
HETATM    1  N1  UNL     1      -8.864   1.735  -1.732  1.00  0.00           N  
HETATM    2  C1  UNL     1      -7.552   1.375  -1.267  1.00  0.00           C  
HETATM    3  N2  UNL     1      -6.466   1.532  -2.037  1.00  0.00           N  
HETATM    4  C2  UNL     1      -5.208   1.207  -1.642  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.212   1.362  -2.375  1.00  0.00           O  
HETATM    6  C3  UNL     1      -5.043   0.692  -0.392  1.00  0.00           C  
HETATM    7  C4  UNL     1      -6.150   0.525   0.412  1.00  0.00           C  
HETATM    8  N3  UNL     1      -7.396   0.868  -0.034  1.00  0.00           N  
HETATM    9  N4  UNL     1      -5.960  -0.010   1.707  1.00  0.00           N  
HETATM   10  C5  UNL     1      -4.701  -0.474   2.238  1.00  0.00           C  
HETATM   11  C6  UNL     1      -3.644  -0.629   1.184  1.00  0.00           C  
HETATM   12  C7  UNL     1      -2.302  -0.305   1.791  1.00  0.00           C  
HETATM   13  N5  UNL     1      -1.586   0.073   0.558  1.00  0.00           N  
HETATM   14  C8  UNL     1      -0.229  -0.169   0.294  1.00  0.00           C  
HETATM   15  C9  UNL     1       0.618  -0.773   1.197  1.00  0.00           C  
HETATM   16  C10 UNL     1       1.949  -1.005   0.925  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.499  -0.638  -0.277  1.00  0.00           C  
HETATM   18  C12 UNL     1       3.890  -0.835  -0.655  1.00  0.00           C  
HETATM   19  O2  UNL     1       4.260  -0.661  -1.849  1.00  0.00           O  
HETATM   20  N6  UNL     1       4.819  -1.223   0.331  1.00  0.00           N  
HETATM   21  C13 UNL     1       6.217  -1.414  -0.093  1.00  0.00           C  
HETATM   22  C14 UNL     1       7.023  -0.486   0.785  1.00  0.00           C  
HETATM   23  C15 UNL     1       6.565   0.924   0.570  1.00  0.00           C  
HETATM   24  C16 UNL     1       6.756   1.407  -0.813  1.00  0.00           C  
HETATM   25  O3  UNL     1       7.307   0.714  -1.697  1.00  0.00           O  
HETATM   26  O4  UNL     1       6.318   2.688  -1.191  1.00  0.00           O  
HETATM   27  C17 UNL     1       6.605  -2.844   0.171  1.00  0.00           C  
HETATM   28  O5  UNL     1       7.357  -3.143   1.122  1.00  0.00           O  
HETATM   29  O6  UNL     1       6.111  -3.822  -0.663  1.00  0.00           O1-
HETATM   30  C18 UNL     1       1.660  -0.023  -1.209  1.00  0.00           C  
HETATM   31  C19 UNL     1       0.335   0.196  -0.912  1.00  0.00           C  
HETATM   32  C20 UNL     1      -2.583   0.711  -0.236  1.00  0.00           C  
HETATM   33  N7  UNL     1      -3.754   0.319   0.122  1.00  0.00           N1+
HETATM   34  H1  UNL     1      -9.421   2.504  -1.350  1.00  0.00           H  
HETATM   35  H2  UNL     1      -9.268   1.171  -2.510  1.00  0.00           H  
HETATM   36  H3  UNL     1      -8.217   0.735   0.585  1.00  0.00           H  
HETATM   37  H4  UNL     1      -6.793  -0.079   2.338  1.00  0.00           H  
HETATM   38  H5  UNL     1      -4.404   0.222   3.050  1.00  0.00           H  
HETATM   39  H6  UNL     1      -4.854  -1.480   2.704  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.581  -1.651   0.760  1.00  0.00           H  
HETATM   41  H8  UNL     1      -2.422   0.586   2.457  1.00  0.00           H  
HETATM   42  H9  UNL     1      -1.836  -1.153   2.295  1.00  0.00           H  
HETATM   43  H10 UNL     1       0.193  -1.071   2.159  1.00  0.00           H  
HETATM   44  H11 UNL     1       2.576  -1.482   1.656  1.00  0.00           H  
HETATM   45  H12 UNL     1       4.539  -1.368   1.311  1.00  0.00           H  
HETATM   46  H13 UNL     1       6.318  -1.249  -1.161  1.00  0.00           H  
HETATM   47  H14 UNL     1       6.806  -0.737   1.846  1.00  0.00           H  
HETATM   48  H15 UNL     1       8.110  -0.557   0.569  1.00  0.00           H  
HETATM   49  H16 UNL     1       5.465   1.002   0.817  1.00  0.00           H  
HETATM   50  H17 UNL     1       7.141   1.608   1.259  1.00  0.00           H  
HETATM   51  H18 UNL     1       5.526   2.754  -1.818  1.00  0.00           H  
HETATM   52  H19 UNL     1       2.092   0.275  -2.176  1.00  0.00           H  
HETATM   53  H20 UNL     1      -0.300   0.677  -1.654  1.00  0.00           H  
HETATM   54  H21 UNL     1      -2.310   1.421  -1.020  1.00  0.00           H  
CONECT    1    2   34   35
CONECT    2    3    3    8
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   33
CONECT    7    8    9
CONECT    8   36
CONECT    9   10   37
CONECT   10   11   38   39
CONECT   11   12   33   40
CONECT   12   13   41   42
CONECT   13   14   32
CONECT   14   15   15   31
CONECT   15   16   43
CONECT   16   17   17   44
CONECT   17   18   30
CONECT   18   19   19   20
CONECT   20   21   45
CONECT   21   22   27   46
CONECT   22   23   47   48
CONECT   23   24   49   50
CONECT   24   25   25   26
CONECT   26   51
CONECT   27   28   28   29
CONECT   30   31   31   52
CONECT   31   53
CONECT   32   33   33   54
END

HMDB0001354
     RDKit          3D
5,10-Methenyltetrahydrofolic acid
 54 57  0  0  0  0  0  0  0  0999 V2000
   -8.8642    1.7349   -1.7321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5520    1.3753   -1.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4659    1.5324   -2.0374 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2076    1.2072   -1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.3619   -2.3754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0426    0.6924   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1500    0.5250    0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3956    0.8683   -0.0338 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9600   -0.0100    1.7067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7011   -0.4744    2.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6437   -0.6293    1.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3018   -0.3055    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5862    0.0731    0.5578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288   -0.1688    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.7731    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494   -1.0054    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987   -0.6380   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8903   -0.8352   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600   -0.6610   -1.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193   -1.2232    0.3313 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2175   -1.4141   -0.0935 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0231   -0.4861    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647    0.9236    0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7564    1.4067   -0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3070    0.7139   -1.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3175    2.6877   -1.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6055   -2.8440    0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3572   -3.1432    1.1225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110   -3.8223   -0.6630 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6597   -0.0234   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351    0.1961   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833    0.7110   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7541    0.3191    0.1216 N   0  0  0  0  0  4  0  0  0  0  0  0
   -9.4205    2.5045   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2683    1.1707   -2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2175    0.7352    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -0.0785    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4044    0.2215    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8544   -1.4799    2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -1.6513    0.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217    0.5863    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -1.1534    2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931   -1.0714    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763   -1.4818    1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392   -1.3677    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3182   -1.2493   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8056   -0.7366    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103   -0.5572    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646    1.0017    0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1412    1.6077    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5262    2.7540   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    0.2754   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.6770   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    1.4212   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 13 32  1  0
 32 33  2  0
  8  2  1  0
 33 11  1  0
 33  6  1  0
 31 14  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 30 52  1  0
 31 53  1  0
 32 54  1  0
M  CHG  2  29  -1  33   1
M  END

Synonyms

Value	Source
5,10-Methenyltetrahydrofolate	Generator
5,10-Methenyl-THF	HMDB
Anhydro-leucovorin	HMDB
Anhydro-leucovorin a	HMDB
Anhydroleucovorin	HMDB
Anhydroleucovorin a	HMDB
CH-THF	HMDB
Methenyl-tetrahydrofolate	HMDB
Methenyl-THF	HMDB
Methenyltetrahydrofolate	HMDB
Methenyltetrahydrofolic acid	HMDB
N5-N10-CH-THF	HMDB
N5-N10-Methenyltetrahydrofolate	HMDB
5,10-Methenyltetrahydropteroylglutamate	HMDB
N5,N10-Methenyl tetrahydrofolate	HMDB

Molecular Formula

C₂₀H₂₁N₇O₆

Average Mass

455.424

Monoisotopic Mass

455.155331439

IUPAC Name

(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium

Traditional Name

(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium

CAS Registry Number

Not Available

SMILES

[H][C@@]12CN(C=[N+]1C1=C(NC2)NC(N)=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C([O-])=O

InChI Identifier

InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1

InChI Key

MEANFMOQMXYMCT-OLZOCXBDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Tetrahydrofolic acids

Alternative Parents

Substituents

Tetrahydrofolic acid
Glutamic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Hippuric acid or derivatives
Alpha-amino acid or derivatives
Benzamide
Benzoic acid or derivatives
Aniline or substituted anilines
Benzoyl
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Pyrimidine
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous amide
Heteroaromatic compound
2-imidazoline
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid salt
Amino acid or derivatives
Amidine
Azacycle
Carboxylic acid amidine
Organic 1,3-dipolar compound
Carboxylic acid derivative
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid
Secondary amine
Organic oxygen compound
Amine
Carbonyl group
Organic salt
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organic zwitterion
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	-0.68	ALOGPS
logP	-3.3	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.99	ChemAxon
pKa (Strongest Basic)	2.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	196.77 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	155.82 m³·mol⁻¹	ChemAxon
Polarizability	45.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-2408900000-90c26f197ed01948843b	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0230-9506630000-d9b025a3f36832b17d97	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000900000-9a74d30be444557240b0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000900000-87ffec278a0d552070d3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9210100000-8e44a81962b4227dbc32	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000900000-6e21d81553cf048dcee3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2000900000-e3e2170131566f2c34e9	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300100000-8e0fa01b9b99e8b1fea8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0003900000-a08e1d1cb1452492cc40	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-2109100000-a099f262b4e99916ab71	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-0396000000-4a34a1ca0c2780791f62	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f79-0004900000-b7d25e9a9f2b33373222	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001u-4129500000-674f21af43f4a24fc9aa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f9y-9643100000-a3b87dfc44080a520c03	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	478.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	262.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	194.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	352.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	251.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	196.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	636.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	692.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	295.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	152.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	345.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	161.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	93.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	317.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	481.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	56.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	236.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	869.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	627.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_1	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N)=NC4=O)C=C1)C(=O)[O-]	standard non polar	2025-10-24	2045.54
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_2	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C4)C=[N+]23)[NH]1	standard non polar	2025-10-24	1351.55
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_3	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]2C2=C1[NH]C(N)=NC2=O	standard non polar	2025-10-24	2082.42
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_4	C[Si](C)(C)N1C(N)=NC(=O)C2=C1NC[C@@H]1CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]21	standard non polar	2025-10-24	1551.74
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_5	C[Si](C)(C)N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N)=NC4=O)C=C1)[C@@H](CCC(=O)O)C(=O)[O-]	standard non polar	2025-10-24	1640.16
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_6	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])C=C4)C=[N+]23)[NH]1	standard non polar	2025-10-24	2068.4
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_7	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N)=NC4=O)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1899.64
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_8	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N)=NC4=O)C=C1)C(=O)[O-]	standard non polar	2025-10-24	1822.92
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_9	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C([NH]C(N)=NC4=O)N([Si](C)(C)C)C[C@@H]3C2)C=C1)C(=O)[O-]	standard non polar	2025-10-24	2428.89
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_10	C[Si](C)(C)N(C1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C4)C=[N+]23)[NH]1)[Si](C)(C)C	standard non polar	2025-10-24	1031.13
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_11	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C4)C=[N+]23)N1[Si](C)(C)C	standard non polar	2025-10-24	2330.55
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_12	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C[C@@H]1CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]21	standard non polar	2025-10-24	1328.88
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_13	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)[NH]1	standard non polar	2025-10-24	1266.72
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_14	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]2C2=C1[NH]C(N)=NC2=O	standard non polar	2025-10-24	1880.05
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_15	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]2C2=C1N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	2129.91
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_16	C[Si](C)(C)N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N)=NC4=O)C=C1)[C@@H](CCC(=O)O)C(=O)[O-]	standard non polar	2025-10-24	3234.23
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_17	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)C(=O)[O-]	standard non polar	2025-10-24	2289.34
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_18	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])C=C4)C=[N+]23)N1[Si](C)(C)C	standard non polar	2025-10-24	2941.86
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_19	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C[C@@H]1CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])C=C3)C=[N+]21	standard non polar	2025-10-24	1832.33
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_20	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)[NH]1	standard non polar	2025-10-24	2996.35
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_21	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N)=NC4=O)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	2286.73
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_22	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C([NH]C(N)=NC4=O)N([Si](C)(C)C)C[C@@H]3C2)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	2408.62
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_23	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(N([Si](C)(C)C)C[C@@H]3C2)N([Si](C)(C)C)C(N)=NC4=O)C=C1)C(=O)[O-]	standard non polar	2025-10-24	1730.6
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_24	C[Si](C)(C)N(C1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C4)C=[N+]23)N1[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2747.9
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_25	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]2C2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	2363.21
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_26	C[Si](C)(C)N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)[C@@H](CCC(=O)O)C(=O)[O-]	standard non polar	2025-10-24	1423.86
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_27	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)C[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C4)C=[N+]23)N1[Si](C)(C)C	standard non polar	2025-10-24	2504.02
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_28	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)N1[Si](C)(C)C	standard non polar	2025-10-24	1241.04
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_29	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C[C@@H]1CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]21	standard non polar	2025-10-24	1526.79
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_30	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]2C2=C1N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	1068.3
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_31	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1832.26
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_32	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)C(=O)[O-]	standard non polar	2025-10-24	1817.77
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_33	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)N([Si](C)(C)C)C[C@@H]3C2)C=C1)C(=O)[O-]	standard non polar	2025-10-24	2412.28
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_34	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)C[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])C=C4)C=[N+]23)N1[Si](C)(C)C	standard non polar	2025-10-24	2936.31
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_35	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)N1[Si](C)(C)C	standard non polar	2025-10-24	3911.89
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_36	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C[C@@H]1CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]21	standard non polar	2025-10-24	3951.11
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_37	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(N([Si](C)(C)C)C[C@@H]3C2)N([Si](C)(C)C)C(N)=NC4=O)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1722.28
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_38	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]2C2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1733.21
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_39	C[Si](C)(C)N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)[C@@H](CCC(=O)O)C(=O)[O-]	standard non polar	2025-10-24	2797.24
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_40	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]2C2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1052.38
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_41	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)C[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)N1[Si](C)(C)C	standard non polar	2025-10-24	1804.17
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_42	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	2377.12
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_43	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)N([Si](C)(C)C)C[C@@H]3C2)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	2341.23
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_44	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(N([Si](C)(C)C)C[C@@H]3C2)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)C(=O)[O-]	standard non polar	2025-10-24	2449.13
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_45	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)C[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)N1[Si](C)(C)C	standard non polar	2025-10-24	2196.35
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_46	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]2C2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1982.08
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_47	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(N([Si](C)(C)C)C[C@@H]3C2)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1245.14
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_1	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N)=NC4=O)C=C1)C(=O)[O-]	standard polar	2025-10-24	2270.8
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_2	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C4)C=[N+]23)[NH]1	standard polar	2025-10-24	2300.56
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_3	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]2C2=C1[NH]C(N)=NC2=O	standard polar	2025-10-24	2348.66
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_4	C[Si](C)(C)N1C(N)=NC(=O)C2=C1NC[C@@H]1CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]21	standard polar	2025-10-24	1221.8
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_5	C[Si](C)(C)N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N)=NC4=O)C=C1)[C@@H](CCC(=O)O)C(=O)[O-]	standard polar	2025-10-24	421.382
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_6	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])C=C4)C=[N+]23)[NH]1	standard polar	2025-10-24	2059.57
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_7	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N)=NC4=O)C=C1)[Si](C)(C)C	standard polar	2025-10-24	1334.04
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_8	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N)=NC4=O)C=C1)C(=O)[O-]	standard polar	2025-10-24	1910.19
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_9	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C([NH]C(N)=NC4=O)N([Si](C)(C)C)C[C@@H]3C2)C=C1)C(=O)[O-]	standard polar	2025-10-24	3107.12
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_10	C[Si](C)(C)N(C1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C4)C=[N+]23)[NH]1)[Si](C)(C)C	standard polar	2025-10-24	2545.22
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_11	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C4)C=[N+]23)N1[Si](C)(C)C	standard polar	2025-10-24	2558.17
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_12	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C[C@@H]1CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]21	standard polar	2025-10-24	2227.14
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_13	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)[NH]1	standard polar	2025-10-24	2462.32
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_14	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]2C2=C1[NH]C(N)=NC2=O	standard polar	2025-10-24	2722.01
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_15	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]2C2=C1N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	2886.98
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_16	C[Si](C)(C)N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N)=NC4=O)C=C1)[C@@H](CCC(=O)O)C(=O)[O-]	standard polar	2025-10-24	2458.47
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_17	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)C(=O)[O-]	standard polar	2025-10-24	2243.72
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_18	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])C=C4)C=[N+]23)N1[Si](C)(C)C	standard polar	2025-10-24	1610.25
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_19	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C[C@@H]1CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])C=C3)C=[N+]21	standard polar	2025-10-24	1912.48
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_20	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)[NH]1	standard polar	2025-10-24	3059.81
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_21	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N)=NC4=O)C=C1)[Si](C)(C)C	standard polar	2025-10-24	1920.0
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_22	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C([NH]C(N)=NC4=O)N([Si](C)(C)C)C[C@@H]3C2)C=C1)[Si](C)(C)C	standard polar	2025-10-24	2789.03
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_23	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(N([Si](C)(C)C)C[C@@H]3C2)N([Si](C)(C)C)C(N)=NC4=O)C=C1)C(=O)[O-]	standard polar	2025-10-24	2680.7
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_24	C[Si](C)(C)N(C1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C4)C=[N+]23)N1[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1973.43
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_25	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]2C2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	1708.77
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_26	C[Si](C)(C)N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)[C@@H](CCC(=O)O)C(=O)[O-]	standard polar	2025-10-24	1811.25
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_27	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)C[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C4)C=[N+]23)N1[Si](C)(C)C	standard polar	2025-10-24	629.535
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_28	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)N1[Si](C)(C)C	standard polar	2025-10-24	1142.96
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_29	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C[C@@H]1CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]21	standard polar	2025-10-24	2915.51
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_30	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]2C2=C1N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	1880.64
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_31	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)[Si](C)(C)C	standard polar	2025-10-24	1838.62
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_32	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)C(=O)[O-]	standard polar	2025-10-24	2523.41
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_33	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)N([Si](C)(C)C)C[C@@H]3C2)C=C1)C(=O)[O-]	standard polar	2025-10-24	2717.63
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_34	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)C[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])C=C4)C=[N+]23)N1[Si](C)(C)C	standard polar	2025-10-24	3874.08
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_35	C[Si](C)(C)NC1=NC(=O)C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)N1[Si](C)(C)C	standard polar	2025-10-24	836.048
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_36	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C[C@@H]1CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]21	standard polar	2025-10-24	2652.73
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_37	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(N([Si](C)(C)C)C[C@@H]3C2)N([Si](C)(C)C)C(N)=NC4=O)C=C1)[Si](C)(C)C	standard polar	2025-10-24	2894.67
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_38	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)[O-])C=C3)C=[N+]2C2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	1835.97
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_39	C[Si](C)(C)N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)[C@@H](CCC(=O)O)C(=O)[O-]	standard polar	2025-10-24	1906.99
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_40	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]2C2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	2855.85
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_41	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)C[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)N1[Si](C)(C)C	standard polar	2025-10-24	2090.52
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_42	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(NC[C@@H]3C2)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)[Si](C)(C)C	standard polar	2025-10-24	2120.65
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_43	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)N([Si](C)(C)C)C[C@@H]3C2)C=C1)[Si](C)(C)C	standard polar	2025-10-24	1805.0
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_44	C[Si](C)(C)OC(=O)CC[C@H](NC(=O)C1=CC=C(N2C=[N+]3C4=C(N([Si](C)(C)C)C[C@@H]3C2)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)C(=O)[O-]	standard polar	2025-10-24	1982.78
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_45	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)C[C@@H]3CN(C4=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C=C4)C=[N+]23)N1[Si](C)(C)C	standard polar	2025-10-24	811.376
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_46	C[Si](C)(C)N1C[C@@H]2CN(C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)[O-])[Si](C)(C)C)C=C3)C=[N+]2C2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	1711.59
Gas Chromatography	5,10-Methenyltetrahydrofolic acid_TMS_47	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)[O-])N(C(=O)C1=CC=C(N2C=[N+]3C4=C(N([Si](C)(C)C)C[C@@H]3C2)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)C=C1)[Si](C)(C)C	standard polar	2025-10-24	1556.03

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191999	Trifunctional purine biosynthetic protein adenosine-3	Enzyme	P22102	Homo sapiens
MMDBp0192325	Formimidoyltransferase-cyclodeaminase	Enzyme	O95954	Homo sapiens
MMDBp0192327	Aminomethyltransferase, mitochondrial	Enzyme	P48728	Homo sapiens
MMDBp0192538	Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial	Unknown	P13995	Homo sapiens
MMDBp0192541	C-1-tetrahydrofolate synthase, cytoplasmic	Enzyme	P11586	Homo sapiens
MMDBp0192979	5-formyltetrahydrofolate cyclo-ligase	Unknown	P49914	Homo sapiens
MMDBp0194061	Probable bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase 2	Unknown	Q9H903	Homo sapiens
MMDBp0194163	Monofunctional C1-tetrahydrofolate synthase, mitochondrial	Enzyme	Q6UB35	Homo sapiens
MMDBp0194164	Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase	Enzyme	Q7Z650	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Name	SMPDB/PathBank	Species
One Carbon Pool by Folate		Escherichia coli Pseudomonas aeruginosa Escherichia coli SMS-3-5 Escherichia coli UTI89 Escherichia coli 55989 Escherichia coli SE11 Mycobacterium marinum M Pseudomonas aeruginosa PA7 Acinetobacter sp. ADP1 Actinobacillus succinogenes 130Z Escherichia coli CFT073 Myxococcus xanthus DK 1622 Ochrobactrum anthropi Bacillus subtilis Pseudomonas stutzeri Mycobacterium tuberculosis Klebsiella pneumoniae Bacillus cereus Pseudomonas fluorescens Pf-5 Streptomyces griseus subsp. griseus NBRC 13350 Mycobacterium tuberculosis CDC1551 Bacillus amyloliquefaciens Streptococcus pneumoniae Salmonella enterica Staphylococcus aureus Haemophilus influenzae Haemophilus influenzae Rd KW20 Clostridium sporogenes Rhodospirillum rubrum ATCC 11170 Methanoculleus marisnigri Lactobacillus fermentum IFO 3956 Streptococcus pneumoniae TIGR4 Aromatoleum aromaticum EbN1 Saccharopolyspora erythraea NRRL 2338 Streptomyces avermitilis MA-4680 Shewanella denitrificans OS217 Acinetobacter baumannii Akkermansia muciniphila ATCC BAA-835 Alistipes finegoldii DSM 17242 Anaerostipes caccae Anaerostipes hadrus Bacillus cereus AH187 (F4810/72) Bacillus halodurans C-125 Alkalihalobacillus pseudofirmus OF4 Bacillus timonensis 10403023 Bacteroides caccae Bacteroides cellulosilyticus Bacteroides eggerthii Bacteroides fragilis Bacteroides fragilis 638R Bacteroides fragilis YCH46 Bacteroides ovatus Bacteroides stercoris Bacteroides stercoris ATCC 43183 Bacteroides thetaiotaomicron Bacteroides thetaiotaomicron VPI-5482 Bacteroides vulgatus Bacteroides xylanisolvens XB1A Bifidobacterium Bifidum Bifidobacterium adolescentis Bifidobacterium adolescentis ATCC 15703 Bifidobacterium animalis subsp. lactis Bifidobacterium bifidum BGN4 Bifidobacterium bifidum PRL2010 Bifidobacterium longum Bifidobacterium longum DJO10A Bifidobacterium longum NCC2705 Bifidobacterium longum subsp. longum JDM301 Bifidobacterium mongoliense DSM 21395 Bifidobacterium thermophilum RBL67 Blautia obeum A2-162 Blautia obeum ATCC 29174 Brevibacillus brevis NBRC 100599 Clostridium beijerinckii NCIMB 8052 Clostridium botulinum Clostridium saccharolyticum Clostridium sticklandii Collinsella aerofaciens Coprococcus catus GD/7 Dorea formicigenerans ATCC 27755 Dysgonomonas gadei ATCC BAA-286 Enterococcus faecalis Eubacterium rectale ATCC 33656 Geobacter metallireducens Haemophilus parainfluenzae T3T1 Limosilactobacillus fermentum Lactobacillus reuteri Megamonas hypermegale Methylobacterium nodulans Ochrobactrum anthropi ATCC 49188 Ochrobactrum intermedium LMG 3301 Odoribacter splanchnicus DSM 20712 Parabacteroides distasonis Parabacteroides distasonis ATCC 8503 Parabacteroides goldsteinii dnLKV18 Porphyromonas asaccharolytica DSM 20707 Porphyromonas endodontalis ATCC 35406 Porphyromonas gingivalis ATCC 33277 Prevotella intermedia Prevotella ruminicola 23 Roseburia hominis A2-183 Streptococcus salivarius lactobacillus crispatus lactobacillus vaginalis Buchnera aphidicola Pelobacter carbinolicus Thermus thermophilus Comamonas testosteroni Burkholderia cepacia Pseudomonas fluorescens Pseudomonas mendocina Pseudomonas putida Pseudomonas syringae Xanthomonas campestris Bradyrhizobium japonicum Mesorhizobium loti Sinorhizobium meliloti Methylococcus capsulatus Moraxella catarrhalis Neisseria flavescens Neisseria gonorrhoeae Neisseria mucosa Acidiphilium cryptum Chromobacterium violaceum Citrobacter koseri Proteus mirabilis Shigella boydii Shigella dysenteriae Shigella flexneri Shigella sonnei Aeromonas hydrophila Vibrio cholerae Vibrio vulnificus Bacteroides uniformis Fusobacterium periodonticum Fusobacterium ulcerans Syntrophomonas wolfei Desulfovibrio salexigens Desulfovibrio piger Acidithiobacillus ferrooxidans Cytophaga hutchinsonii Capnocytophaga ochracea Capnocytophaga sputigena Rhodopseudomonas palustris Chlorobium phaeobacteroides Leuconostoc mesenteroides Ruminococcus albus Staphylococcus epidermidis Deinococcus radiodurans Streptococcus gordonii Streptococcus oralis Streptococcus sanguinis Streptococcus mutans Streptococcus agalactiae Streptococcus pyogenes Streptococcus dysgalactiae Streptococcus equinus Streptococcus equi Streptococcus uberis Enterococcus gallinarum Bacillus licheniformis Priestia megaterium Bacillus mycoides Bacillus pumilus Bacillus thuringiensis Clostridium butyricum Moorella thermoacetica Clostridium kluyveri Weissella confusa Lactobacillus helveticus Lactobacillus plantarum Lactobacillus sakei Lactobacillus amylovorus Lactobacillus coryniformis Lactobacillus salivarius Listeria monocytogenes Actinomyces viscosus Bifidobacterium angulatum Cellulomonas flavigena Corynebacterium diphtheriae Corynebacterium glutamicum Mycobacterium avium Desulfobacterium autotrophicum Thermotoga neapolitana Xylella fastidiosa Roseobacter denitrificans Bifidobacterium pseudocatenulatum Staphylococcus lugdunensis Acidothermus cellulolyticus Alistipes putredinis Neisseria subflava Staphylococcus saprophyticus Pelobacter propionicus Caldicellulosiruptor bescii Enterococcus avium Thiobacillus denitrificans Enterococcus casseliflavus Eubacterium ventriosum Sulfurimonas denitrificans Veillonella atypica Veillonella dispar Stenotrophomonas maltophilia Leptotrichia buccalis Actinosynnema mirum Caldicellulosiruptor saccharolyticus Enterococcus cecorum Streptococcus cristatus Enterococcus durans Blautia hydrogenotrophica Acidimicrobium ferrooxidans Desulfotomaculum reducens Burkholderia vietnamiensis Holdemania filiformis Sodalis glossinidius Streptococcus peroris Enterobacter cancerogenus Alloprevotella tannerae Streptococcus constellatus Bifidobacterium gallicum Bacillus clausii Bacillus pseudofirmus Clostridium methylpentosum Bacillus selenitireducens Achromobacter xylosoxidans Burkholderia multivorans Dorea longicatena Burkholderia cenocepacia Actinomyces urogenitalis Methylibium petroleiphilum Citrobacter youngae Leuconostoc kimchii Collinsella stercoris Streptococcus lutetiensis Burkholderia ambifaria Prevotella copri Ilyobacter polytropus Marvinbryantia formatexigens Alicycliphilus denitrificans Desulfovibrio magneticus Shewanella denitrificans Methylocella silvestris Bacteroides massiliensis Escherichia albertii Dialister invisus Geobacter bemidjiensis Lactobacillus antri Streptococcus pseudopneumoniae Bacteroides nordii Bacteroides plebeius Phocaeicola coprocola Bacteroides pyogenes Geobacter lovleyi Streptococcus gallolyticus Bacteroides intestinalis Bacteroides salanitronis Coprococcus comes Actinomyces oris Bacteroides fluxus Bacteroides oleiciplenus Bacteroides faecis Agrobacterium tumefaciens Alistipes finegoldii Alistipes shahii Bacteroides helcogenes Bacteroides xylanisolvens Bifidobacterium breve Bifidobacterium catenulatum Blautia obeum Clostridium beijerinckii Dorea formicigenerans Dysgonomonas gadei Enterococcus faecium Enterococcus hirae Gemella sanguinis Haemophilus parainfluenzae Klebsiella variicola Lactobacillus rhamnosus Lactobacillus ruminis Lactococcus lactis Leuconostoc citreum Odoribacter splanchnicus Parabacteroides goldsteinii Porphyromonas asaccharolytica Prevotella ruminicola Streptococcus mitis Streptococcus parasanguinis Streptococcus suis Streptococcus thermophiles Veillonella parvula Gemella haemolysans Rothia dentocariosa Rothia mucilaginosa Actinomyces graevenitzii Barnesiella intestinihominis Achromobacter xylosoxidans A8 Acinetobacter baumannii SDF Acinetobacter baumannii ACICU Acinetobacter baumannii AB0057 Acinetobacter baumannii AB307-0294 Actinobacillus pleuropneumoniae serovar 5b str. L20 Actinobacillus pleuropneumoniae serovar 3 str. JL03 Actinobacillus pleuropneumoniae serovar 7 str. AP76 Aeromonas hydrophila subsp. hydrophila ATCC 7966 Agrobacterium tumefaciens str. C58 Bacillus cereus ATCC 10987 Bacillus megaterium QM B1551 Bacillus thuringiensis serovar konkukian str. 97-27 Bacillus licheniformis ATCC 14580 Bacillus clausii KSM-K16 Bacillus amyloliquefaciens FZB42 Bacillus pumilus SAFR-032 Bacillus cereus B4264 Bacillus cereus AH820 Bacillus cereus G9842 Bacillus cereus Q1 Priestia megaterium DSM 319 Bacillus subtilis subsp. spizizenii str. W23 Bacillus amyloliquefaciens DSM 7 Bartonella quintana str. Toulouse Bifidobacterium animalis subsp. lactis AD011 Bradyrhizobium japonicum USDA 110 Buchnera aphidicola str. APS (Acyrthosiphon pisum) Buchnera aphidicola str. Sg (Schizaphis graminum) Buchnera aphidicola str. Bp (Baizongia pistaciae) Buchnera aphidicola str. 5A (Acyrthosiphon pisum) Capnocytophaga ochracea DSM 7271 Citrobacter koseri ATCC BAA-895 Clostridium botulinum A str. Hall Clostridium botulinum B1 str. Okra Clostridium botulinum A2 str. Kyoto Clostridium botulinum Ba4 str. 657 Clostridium sticklandii DSM 519 Corynebacterium aurimucosum ATCC 700975 Corynebacterium kroppenstedtii DSM 44385 Cronobacter sakazakii ATCC BAA-894 Delftia acidovorans SPH-1 Dyadobacter fermentans DSM 18053 Enterobacter cloacae subsp. cloacae ATCC 13047 Escherichia coli APEC O1 Escherichia coli E24377A Escherichia coli O127:H6 str. E2348/69 Escherichia coli UMN026 Escherichia fergusonii ATCC 35469 Escherichia coli ED1a Escherichia coli IAI39 Haemophilus influenzae 86-028NP Haemophilus influenzae PittGG Klebsiella pneumoniae subsp. pneumoniae MGH 78578 Kocuria rhizophila DC2201 Kytococcus sedentarius DSM 20547 Lactobacillus plantarum WCFS1 Lactobacillus salivarius UCC118 Lactobacillus acidophilus NCFM Lactobacillus sakei subsp. sakei 23K Lactobacillus brevis ATCC 367 Lactobacillus casei ATCC 334 Lactobacillus reuteri DSM 20016 Lactobacillus helveticus DPC 4571 Lactobacillus amylovorus GRL 1112 Lactobacillus reuteri SD2112 Lactococcus lactis subsp. lactis Il1403 Lactococcus lactis subsp. cremoris SK11 Lactococcus lactis subsp. cremoris MG1363 Laribacter hongkongensis HLHK9 Leptotrichia buccalis C-1013-b Leuconostoc mesenteroides subsp. mesenteroides ATCC 8293 Lysinibacillus sphaericus C3-41 Mesorhizobium loti MAFF303099 Methylobacterium radiotolerans JCM 2831 Methylobacterium populi BJ001 Micrococcus luteus NCTC 2665 Mobiluncus curtisii ATCC 43063 Mycobacterium avium subsp. paratuberculosis K-10 Mycobacterium avium 104 Neisseria gonorrhoeae FA 1090 Neisseria meningitidis MC58 Neisseria meningitidis Z2491 Neisseria meningitidis FAM18 Neisseria gonorrhoeae NCCP11945 Tropheryma whipplei str. Twist Escherichia coli 042 Acinetobacter calcoaceticus PHEA-2 Edwardsiella tarda FL6-60 Bifidobacterium animalis subsp. lactis CNCM I-2494 Pediococcus pentosaceus ATCC 25745 Porphyromonas gingivalis W83 Propionibacterium freudenreichii subsp. shermanii CIRM-BIA1 Proteus mirabilis HI4320 Pseudomonas putida KT2440 Pseudomonas fluorescens Pf0-1 Pseudomonas stutzeri A1501 Pseudomonas fluorescens SBW25 Pseudomonas putida GB-1 Rhizobium leguminosarum bv. viciae 3841 Rhizobium leguminosarum bv. trifolii WSM2304 Rhodococcus erythropolis PR4 Rothia mucilaginosa DY-18 Rothia dentocariosa ATCC 17931 Ruminococcus albus 7 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Salmonella enterica subsp. enterica serovar Newport str. SL254 Salmonella enterica subsp. enterica serovar Heidelberg str. SL476 Salmonella enterica subsp. enterica serovar Agona str. SL483 Salmonella enterica subsp. enterica serovar Dublin str. CT02021853 Shigella sonnei Ss046 Shigella dysenteriae Sd197 Shigella flexneri 5 str. 8401 Spirosoma linguale DSM 74 Staphylococcus aureus subsp. aureus Mu50 Staphylococcus aureus subsp. aureus COL Staphylococcus aureus subsp. aureus MRSA252 Staphylococcus epidermidis RP62A Staphylococcus epidermidis ATCC 12228 Staphylococcus haemolyticus JCSC1435 Staphylococcus saprophyticus subsp. saprophyticus ATCC 15305 Staphylococcus aureus subsp. aureus NCTC 8325 Stenotrophomonas maltophilia K279a Stenotrophomonas maltophilia R551-3 Streptococcus agalactiae 2603V/R Streptococcus mutans UA159 Streptococcus agalactiae NEM316 Streptococcus thermophilus LMG 18311 Streptococcus pyogenes MGAS9429 Streptococcus pneumoniae D39 Streptococcus sanguinis SK36 Streptococcus gordonii str. Challis substr. CH1 Streptococcus pneumoniae Hungary19A-6 Streptococcus pyogenes NZ131 Streptococcus uberis 0140J Streptococcus pneumoniae JJA Streptococcus equi subsp. equi 4047 Streptococcus oralis Uo5 Vibrio parahaemolyticus RIMD 2210633 Yersinia enterocolitica subsp. enterocolitica 8081 Yersinia pseudotuberculosis IP 31758 Aquifex aeolicus Bacteroides cellulosilyticus DSM 14838 Bacteroides eggerthii 1_2_48FAA Bacteroides fluxus YIT 12057 Bacteroides graminisolvens Bacteroides graminisolvens DSM 19988 = JCM 15093 Bacteroides intestinalis DSM 17393 Bacteroides nordii CL02T12C05 Bacteroides oleiciplenus YIT 12058 Bacteroides ovatus ATCC 8483 Bacteroides pyogenes DSM 20611 = JCM 6294 Bacteroides uniformis ATCC 8492 Bacteroides xylanisolvens SD CC 1b Bacteroides sp. 1_1_14 Bacteroides sp. 1_1_30 Bacteroides sp. 2_1_22 Bacteroides sp. 2_2_4 Bacteroides sp. D2 Bacteroides sp. D20 Bacteroides sp. D22 Barnesiella intestinihominis YIT 11860 Butyricimonas virosa Odoribacter laneus YIT 12061 Porphyromonas endodontalis Porphyromonas uenonis 60-3 Alloprevotella tannerae ATCC 51259 Paraprevotella clara YIT 11840 Paraprevotella xylaniphila YIT 11841 Prevotella bivia DSM 20514 Prevotella buccae ATCC 33574 Prevotella denticola Prevotella disiens FB035-09AN Prevotella loescheii DSM 19665 = JCM 12249 = ATCC 15930 Prevotella oralis ATCC 33269 Prevotella pallens ATCC 700821 Prevotella salivae DSM 15606 Prevotella shahii DSM 15611 = JCM 12083 Prevotella timonensis CRIS 5C-B1 Alistipes indistinctus YIT 12060 Alistipes putredinis DSM 17216 Parabacteroides johnsonii DSM 18315 Parabacteroides sp. D13 Tannerella forsythia Bacteroides coprophilus DSM 18228 = JCM 13818 Bacteroides dorei DSM 17855 Spirosoma linguale Chlorobium limicola Cetobacterium somerae ATCC BAA-474 Fusobacterium periodonticum 1_1_41FAA Bartonella quintana Beijerinckia indica Bradyrhizobium elkanii Methylobacterium mesophilicum Methylobacterium mesophilicum SR1.6/6 Rhizobium etli Azorhizobium caulinodans Xanthobacter autotrophicus Alcaligenes faecalis Burkholderia cepacia GG4 Lautropia mirabilis Lautropia mirabilis ATCC 51599 Parasutterella excrementihominis YIT 11859 Sutterella parvirubra Sutterella parvirubra YIT 11816 Laribacter hongkongensis Eikenella corrodens Eikenella corrodens ATCC 23834 Kingella oralis Kingella oralis ATCC 51147 Neisseria cinerea ATCC 14685 Neisseria elongata Neisseria elongata subsp. glycolytica ATCC 29315 Neisseria macacae Neisseria macacae ATCC 33926 Neisseria meningitidis Neisseria mucosa ATCC 25996 Neisseria subflava NJ9703 Nitrosospira multiformis Methyloversatilis universalis Methyloversatilis universalis FAM5 Bilophila wadsworthia 3_1_6 Desulfovibrio piger ATCC 29098 Aeromonas caviae Aeromonas media Aeromonas veronii Succinatimonas hippei Succinatimonas hippei YIT 12066 Succinivibrio dextrinosolvens Allochromatium vinosum Cedecea davisae Cedecea davisae DSM 4568 Citrobacter amalonaticus Citrobacter amalonaticus Y19 Citrobacter freundii Citrobacter youngae ATCC 29220 Enterobacter hormaechei Escherichia albertii TW07627 Klebsiella aerogenes Salmonella Salmonella enterica subsp. enterica serovar Typhimurium Trabulsiella guamensis Trabulsiella guamensis ATCC 49490 Tatumella ptyseos Tatumella ptyseos ATCC 33301 Edwardsiella tarda Edwardsiella tarda ATCC 23685 Hafnia alvei Hafnia alvei ATCC 51873 Morganella morganii Morganella morganii subsp. morganii KT Providencia rustigianii DSM 4541 Providencia stuartii ATCC 25827 Serratia marcescens subsp. marcescens Db11 Yersinia enterocolitica Yersinia pestis Yersinia pseudotuberculosis Plesiomonas shigelloides 302-73 Legionella pneumophila Actinobacillus pleuropneumoniae Aggregatibacter aphrophilus Haemophilus haemolyticus Haemophilus sputorum Acinetobacter pittii Acinetobacter haemolyticus Acinetobacter johnsonii Acinetobacter johnsonii SH046 Acinetobacter junii SH205 Francisella tularensis Grimontia hollisae CIP 101886 Vibrio fluvialis Vibrio fluvialis PG41 Vibrio parahaemolyticus Vibrio mimicus Leptospira interrogans Actinomyces graevenitzii C83 Actinomyces naeslundii Actinomyces naeslundii str. Howell 279 Actinomyces urogenitalis DSM 15434 Actinomyces viscosus C505 Mobiluncus curtisii Bifidobacterium stercoris JCM 15918 Bifidobacterium angulatum DSM 20098 = JCM 7096 Bifidobacterium boum Bifidobacterium catenulatum DSM 16992 = JCM 1194 = LMG 11043 Bifidobacterium gallicum DSM 20093 = LMG 11596 Bifidobacterium longum subsp. infantis CCUG 52486 Bifidobacterium mongoliense Bifidobacterium pseudocatenulatum DSM 20438 = JCM 1200 = LMG 10505 Bifidobacterium thermacidophilum Bifidobacterium thermophilum Corynebacterium amycolatum Corynebacterium aurimucosum Corynebacterium durum Corynebacterium durum F0235 Corynebacterium tuberculostearicum Corynebacterium tuberculostearicum SK141 Gordonia terrae C-6 Rhodococcus erythropolis Brevibacterium casei Brevibacterium casei S18 Brevibacterium linens Microbacterium oleivorans Kocuria palustris PEL Rothia aeria F0474 Cellulosimicrobium cellulans Tropheryma whipplei Propionibacterium Streptomyces avermitilis Thermomonospora curvata Collinsella intestinalis DSM 13280 Collinsella stercoris DSM 13279 Collinsella tanakaei YIT 12063 Bacillus altitudinis Bacillus infantis NRRL B-14911 Bacillus firmus DS1 Lysinibacillus sphaericus Listeria grayi Listeria grayi DSM 20601 Listeria monocytogenes 10403S Aneurinibacillus aneurinilyticus Aneurinibacillus aneurinilyticus ATCC 12856 Paenibacillus lactis 154 Gemella haemolysans ATCC 10379 Exiguobacterium aurantiacum Abiotrophia defectiva Abiotrophia defectiva ATCC 49176 Enterococcus asini ATCC 700915 Enterococcus caccae ATCC BAA-1240 Enterococcus casseliflavus ATCC 12755 Enterococcus cecorum DSM 20682 = ATCC 43198 Enterococcus dispar ATCC 51266 Enterococcus phoeniculicola ATCC BAA-412 Lactobacillus paracasei subsp. paracasei 8700:2 Lactobacillus rhamnosus LMS2-1 Lactobacillus hilgardii DSM 20176 = ATCC 8290 Lactobacillus salivarius DSM 20555 = ATCC 11741 Lactobacillus antri DSM 16041 Lactobacillus coleohominis 101-4-CHN Lactobacillus vaginalis DSM 5837 = ATCC 49540 Lactobacillus reuteri CF48-3A Lactobacillus reuteri MM4-1A Pediococcus acidilactici DSM 20284 Pediococcus pentosaceus Leuconostoc lactis Leuconostoc mesenteroides subsp. cremoris ATCC 19254 Oenococcus oeni Weissella cibaria Weissella paramesenteroides Weissella paramesenteroides ATCC 33313 Lactococcus garvieae Streptococcus constellatus subsp. pharyngis SK1060 = CCUG 46377 Streptococcus australis ATCC 700641 Streptococcus equi subsp. zooepidemicus H70 Streptococcus equi subsp. zooepidemicus MGCS10565 Streptococcus equinus ATCC 9812 Streptococcus infantis ATCC 700779 Streptococcus vestibularis F0396 Clostridium butyricum E4 str. BoNT E BL5262 Clostridium celatum DSM 1785 Clostridium sartagoforme AAU1 Anaerofustis stercorihominis Anaerofustis stercorihominis DSM 17244 Eubacterium ventriosum ATCC 27560 [Eubacterium] cellulosolvens 6 Anaerostipes caccae DSM 14662 Blautia hydrogenotrophica DSM 10507 Blautia wexlerae Coprococcus comes ATCC 27758 Dorea longicatena DSM 13814 Clostridium asparagiforme DSM 15981 [Clostridium] bolteae ATCC BAA-613 Clostridium citroniae WAL-17108 [Clostridium] hylemonae DSM 15053 [Ruminococcus] gnavus ATCC 29149 [Ruminococcus] lactaris ATCC 29176 [Ruminococcus] torques ATCC 27756 Oribacterium sinus F0268 Roseburia inulinivorans DSM 16841 Flavonifractor plautii ATCC 29863 Pseudoflavonifractor capillosus ATCC 29799 [Eubacterium] siraeum DSM 15702 [Bacteroides] pectinophilus ATCC 43243 Mogibacterium timidum Mogibacterium timidum ATCC 33093 [Clostridium] spiroforme DSM 1552 Holdemania filiformis DSM 12042 Kandleria vitulina Kandleria vitulina DSM 20405 Dialister invisus DSM 15470 Dialister succinatiphilus Dialister succinatiphilus YIT 11850 Veillonella atypica ACS-049-V-Sch6 Veillonella dispar ATCC 17748 Anaerococcus hydrogenalis DSM 7454 Parvimonas micra ATCC 33270 Halococcus morrhuae DSM 1307 Halococcus morrhuae Streptomyces coelicolor A3(2) Bordetella pertussis Tohama I Bordetella parapertussis 12822 Ralstonia eutropha H16 Xanthomonas campestris pv. campestris str. ATCC 33913 Xanthomonas campestris pv. campestris str. B100 Xanthomonas campestris pv. campestris str. 8004 Vibrio cholerae M66-2 Vibrio cholerae O1 biovar El Tor str. N16961 Corynebacterium glutamicum ATCC 13032 Clostridioides difficile 630 Clostridioides difficile NAP08 Shewanella frigidimarina NCIMB 400 Bacillus cytotoxicus NVH 391-98 Bifidobacterium longum subsp. infantis Bifidobacterium longum subsp. longum Lachnoclostridium phytofermentans ISDg Leuconostoc citreum KM20 Streptococcus mitis B6 Streptococcus parasanguinis ATCC 15912 Streptococcus parasanguinis FW213 Streptococcus pasteurianus ATCC 43144 Streptococcus suis GZ1 Acidimicrobium ferrooxidans DSM 10331 Acidothermus cellulolyticus 11B Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446 Alkaliphilus metalliredigens QYMF Alkaliphilus oremlandii OhILAs Amycolatopsis mediterranei U32 Anoxybacillus flavithermus WK1 Arthrobacter sp. FB24 Arthrobacter aurescens TC1 Arthrobacter chlorophenolicus A6 Bacillus selenitireducens MLS10 Beutenbergia cavernae DSM 12333 Bifidobacterium dentium Bd1 Butyrivibrio proteoclasticus B316 Caldicellulosiruptor bescii DSM 6725 Candidatus Desulforudis audaxviator MP104C Carboxydothermus hydrogenoformans Z-2901 Catenulispora acidiphila DSM 44928 Cellulomonas flavigena DSM 20109 Clavibacter michiganensis subsp. michiganensis NCPPB 382 Clostridium thermocellum ATCC 27405 Conexibacter woesei DSM 14684 Corynebacterium jeikeium K411 Corynebacterium glutamicum R Corynebacterium urealyticum DSM 7109 Corynebacterium resistens DSM 45100 Deinococcus radiodurans R1 Deinococcus geothermalis DSM 11300 Deinococcus proteolyticus MRP Desulfotomaculum reducens MI-1 Exiguobacterium sibiricum 255-15 Exiguobacterium sp. AT1b Frankia alni ACN14a Frankia sp. EuI1c Gardnerella vaginalis ATCC 14019 Geobacillus kaustophilus HTA426 Geobacillus thermodenitrificans NG80-2 Gordonia bronchialis DSM 43247 Intrasporangium calvum DSM 43043 Jonesia denitrificans DSM 20603 Kineococcus radiotolerans SRS30216 Kribbella flavida DSM 17836 Lactobacillus crispatus ST1 Leuconostoc kimchii IMSNU 11154 Listeria innocua Clip11262 Listeria welshimeri serovar 6b str. SLCC5334 Macrococcus caseolyticus JCSC5402 Meiothermus ruber DSM 1279 Mycobacterium leprae TN Mycobacterium bovis AF2122/97 Mycobacterium ulcerans Agy99 Mycobacterium vanbaalenii PYR-1 Mycobacterium bovis BCG str. Pasteur 1173P2 Mycobacterium tuberculosis H37Ra Mycobacterium abscessus ATCC 19977 Mycobacterium leprae Br4923 Mycobacterium sp. Spyr1 Mycobacterium sp. JDM601 Mycobacterium canettii CIPT 140010059 Nakamurella multipartita DSM 44233 Natranaerobius thermophilus JW/NM-WN-LF Nocardia farcinica IFM 10152 Nocardioides sp. JS614 Corynebacterium diphtheriae NCTC 13129 Oceanobacillus iheyensis HTE831 Caldicellulosiruptor saccharolyticus DSM 8903 Bacillus tusciae DSM 2912 Thermobaculum terrenum ATCC BAA-798 Oenococcus oeni PSU-1 Pseudonocardia dioxanivorans CB1190 Renibacterium salmoninarum ATCC 33209 Rhodococcus opacus B4 Rhodococcus jostii RHA1 Rhodococcus equi 103S Rubrobacter xylanophilus DSM 9941 Saccharomonospora viridis DSM 43017 Salinispora tropica CNB-440 Sanguibacter keddieii DSM 10542 Slackia heliotrinireducens DSM 20476 Stackebrandtia nassauensis DSM 44728 Staphylococcus carnosus subsp. carnosus TM300 Streptococcus equi subsp. zooepidemicus Streptococcus suis BM407 Streptococcus gallolyticus UCN34 Streptomyces scabiei 87.22 Streptomyces violaceusniger Tu 4113 Streptosporangium roseum DSM 43021 Symbiobacterium thermophilum IAM 14863 Thermoanaerobacter sp. X514 Thermoanaerobacter pseudethanolicus ATCC 33223 Thermoanaerobacter italicus Ab9 Thermoanaerobacterium thermosaccharolyticum DSM 571 Thermobispora bispora DSM 43833 Thermomonospora curvata DSM 43183 Tsukamurella paurometabola DSM 20162 Xylanimonas cellulosilytica DSM 15894 Aspergillus nomiae NRRL 13137 Aspergillus novofumigatus Aspergillus novofumigatus IBT 16806 Aspergillus parasiticus SU-1 Aspergillus phoenicis Aspergillus ruber Aspergillus sclerotioniger Aspergillus glaucus Aspergillus aculeatus ATCC 16872 Aspergillus leporis Aspergillus niger ATCC 1015 Aspergillus oryzae RIB40 Aspergillus terreus NIH2624 Aspergillus wentii Aspergillus clavatus NRRL 1 Aspergillus fischeri NRRL 181 Aspergillus fumigatus A1163 Aspergillus fumigatus Af293 Aspergillus calidoustus Aspergillus nidulans FGSC A4 Aspergillus taichungensis Aspergillus tamarii Aspergillus thermomutatus Aspergillus tubingensis Aspergillus violaceofuscus Aspergillus viridinutans Penicillium brasilianum Penicillium brevicompactum Penicillium canescens Penicillium chermesinum Penicillium citrinum Penicillium concentricum Penicillium daleae Penicillium decumbens Penicillium griseofulvum Penicillium hordei Penicillium italicum Penicillium nalgiovense Penicillium oxalicum Penicillium polonicum Penicillium roqueforti FM164 Penicillium solitum Penicillium steckii Penicillium thymicola Penicillium vulpinum Verticillium alfalfae VaMs.102 Trichoderma arundinaceum Trichoderma asperellum Trichoderma atroviride IMI 206040 Trichoderma citrinoviride Trichoderma harzianum Trichoderma longibrachiatum Trichoderma parareesei Trichoderma reesei QM6a Trichoderma virens Trichoderma virens Gv29-8 Fusarium acutatum Fusarium fujikuroi IMI 58289 Fusarium mangiferae Fusarium nygamai Fusarium proliferatum ET1 Fusarium subglutinans Fusarium verticillioides 7600 Fusarium heterosporum Fusarium equiseti Fusarium oxysporum Fo5176 Fusarium oxysporum f. sp. lycopersici 4287 Fusarium austroamericanum Fusarium graminearum PH-1 Fusarium poae Fusarium pseudograminearum CS3096 Fusarium sporotrichioides Fusarium vanettenii Fusarium vanettenii 77-13-4 Fusarium tricinctum Paraburkholderia graminis C4D1M Schaalia cardiffensis F0333 Schaalia odontolytica ATCC 17982 Schaalia turicensis ACS-279-V-Col4 Mycolicibacterium fortuitum subsp. fortuitum DSM 46621 = ATCC 6841 Rhodococcus hoagii ATCC 33707 Acidipropionibacterium acidipropionici ATCC 4875 Cutibacterium granulosum DSM 20700 Leuconostoc mesenteroides subsp. cremoris Anaerobutyricum hallii DSM 3353 Bacteroides helcogenes P 36-108 Bacteroides salanitronis DSM 18170 Klebsiella aerogenes KCTC 2190 Treponema succinifaciens DSM 2489 Halanaerobium hydrogeniformans Acaryochloris marina MBIC11017 Acidiphilium cryptum JF-5 Acidiphilium multivorum AIU301 Acidithiobacillus ferrooxidans ATCC 23270 Acidobacterium capsulatum ATCC 51196 Acidovorax citrulli AAC00-1 Acidovorax sp. JS42 Acidovorax ebreus TPSY Aeromonas salmonicida subsp. salmonicida A449 Agrobacterium vitis S4 Agrobacterium radiobacter K84 Rhodoferax ferrireducens T118 Alcanivorax borkumensis SK2 Alicycliphilus denitrificans K601 Vibrio fischeri MJ11 Aliivibrio salmonicida LFI1238 Alkalilimnicola ehrlichii MLHE-1 Anabaena variabilis ATCC 29413 Anaeromyxobacter dehalogenans 2CP-C Anaeromyxobacter sp. Fw109-5 Anaeromyxobacter sp. K Anaeromyxobacter dehalogenans 2CP-1 Aquifex aeolicus VF5 Arcobacter nitrofigilis DSM 7299 Azorhizobium caulinodans ORS 571 Azotobacter vinelandii DJ Bartonella bacilliformis KC583 Bartonella tribocorum CIP 105476 Bartonella grahamii as4aup Mannheimia succiniciproducens MBEL55E Beijerinckia indica subsp. indica ATCC 9039 Bordetella petrii DSM 12804 Bordetella avium 197N Bradyrhizobium sp. ORS278 Bradyrhizobium sp. BTAi1 Brucella melitensis bv. 1 str. 16M Brucella abortus bv. 1 str. 9-941 Brucella ovis ATCC 25840 Brucella canis ATCC 23365 Brucella suis ATCC 23445 Brucella abortus S19 Brucella melitensis ATCC 23457 Brucella microti CCM 4915 Burkholderia mallei ATCC 23344 Burkholderia pseudomallei 1710b Burkholderia sp. 383 Burkholderia xenovorans LB400 Burkholderia ambifaria AMMD Burkholderia mallei NCTC 10229 Burkholderia pseudomallei 1106a Burkholderia vietnamiensis G4 Burkholderia cenocepacia MC0-3 Burkholderia ambifaria MC40-6 Burkholderia phymatum STM815 Burkholderia phytofirmans PsJN Burkholderia cenocepacia J2315 Burkholderia rhizoxinica HKI 454 Candidatus Azobacteroides pseudotrichonymphae genomovar. CFP2 Candidatus Hamiltonella defensa 5AT (Acyrthosiphon pisum) Candidatus Koribacter versatilis Ellin345 Candidatus Liberibacter asiaticus str. psy62 Candidatus Pelagibacter ubique HTCC1062 Capnocytophaga canimorsus Cc5 Caulobacter crescentus CB15 Caulobacter crescentus NA1000 Caulobacter segnis ATCC 21756 Cellulophaga algicola DSM 14237 Clostridium lentocellum DSM 5427 Cellvibrio japonicus Ueda107 Cellvibrio gilvus ATCC 13127 Chitinophaga pinensis DSM 2588 Chlorobium tepidum TLS Chlorobium phaeobacteroides DSM 266 Chlorobium limicola DSM 245 Chloroflexus aurantiacus J-10-fl Chloroflexus aggregans DSM 9485 Chloroherpeton thalassium ATCC 35110 Chromohalobacter salexigens DSM 3043 Citrobacter rodentium ICC168 Colwellia psychrerythraea 34H Coprothermobacter proteolyticus DSM 5265 Coxiella burnetii RSA 493 Coxiella burnetii Dugway 5J108-111 Cronobacter turicensis z3032 Cupriavidus metallidurans CH34 Cupriavidus taiwanensis LMG 19424 Cupriavidus necator N-1 Cyanothece sp. ATCC 51142 Cyanothece sp. PCC 8801 Cyanothece sp. PCC 7424 Cytophaga hutchinsonii ATCC 33406 Deinococcus deserti VCD115 Desulfobacterium autotrophicum HRM2 Desulfomicrobium baculatum DSM 4028 Desulfotalea psychrophila LSv54 Desulfovibrio vulgaris str. Hildenborough Desulfovibrio vulgaris DP4 Desulfovibrio magneticus RS-1 Desulfovibrio salexigens DSM 2638 Dichelobacter nodosus VCS1703A Dickeya dadantii Ech703 Dickeya zeae Ech1591 Dickeya dadantii Ech586 Dickeya dadantii 3937 Dinoroseobacter shibae DFL 12 Edwardsiella ictaluri 93-146 Enterobacter sp. 638 Enterobacter cloacae SCF1 Erwinia tasmaniensis Et1/99 Erwinia amylovora CFBP1430 Erwinia billingiae Eb661 Erythrobacter litoralis HTCC2594 Ferrimonas balearica DSM 9799 Fervidobacterium nodosum Rt17-B1 Flavobacterium psychrophilum JIP02/86 Francisella tularensis subsp. holarctica LVS Geobacter metallireducens GS-15 Geobacter uraniireducens Rf4 Geobacter lovleyi SZ Geobacter bemidjiensis Bem Geobacter sp. FRC-32 Geobacter sp. M18 Gloeobacter violaceus PCC 7421 Gluconacetobacter diazotrophicus PAl 5 Gluconobacter oxydans 621H Gramella forsetii KT0803 Granulibacter bethesdensis CGDNIH1 Haemophilus parasuis SH0165 Haemophilus influenzae F3047 Hahella chejuensis KCTC 2396 Haliangium ochraceum DSM 14365 Halorhodospira halophila SL1 Haloterrigena turkmenica DSM 5511 Halothiobacillus neapolitanus c2 Herminiimonas arsenicoxydans Herpetosiphon aurantiacus DSM 785 Hydrogenobacter thermophilus TK-6 Hyphomonas neptunium ATCC 15444 Idiomarina loihiensis L2TR Ilyobacter polytropus DSM 2926 Isosphaera pallida ATCC 43644 Jannaschia sp. CCS1 Janthinobacterium sp. Marseille Klebsiella pneumoniae 342 Leadbetterella byssophila DSM 17132 Legionella pneumophila subsp. pneumophila str. Philadelphia 1 Legionella pneumophila str. Lens Legionella longbeachae NSW150 Leifsonia xyli subsp. xyli str. CTCB07 Leptospira borgpetersenii serovar Hardjo-bovis JB197 Leptothrix cholodnii SP-6 Magnetospirillum magneticum AMB-1 Maricaulis maris MCS10 Marinobacter aquaeolei VT8 Marinomonas mediterranea MMB-1 Marinomonas posidonica IVIA-Po-181 Meiothermus silvanus DSM 9946 Methanoculleus marisnigri JR1 Methylibium petroleiphilum PM1 Methylobacillus flagellatus KT Methylobacterium chloromethanicum CM4 Methylobacterium nodulans ORS 2060 Methylobacterium extorquens AM1 Methylobacterium extorquens DM4 Methylocella silvestris BL2 Methylotenera mobilis JLW8 Methylovorus glucosetrophus SIP3-4 Microbacterium testaceum StLB037 Microcystis aeruginosa NIES-843 Natrialba magadii ATCC 43099 Neisseria meningitidis alpha14 Neisseria lactamica 020-06 Nitrobacter winogradskyi Nb-255 Nitrobacter hamburgensis X14 Nitrosococcus oceani ATCC 19707 Nitrosococcus halophilus Nc4 Nitrosomonas eutropha C91 Nitrosospira multiformis ATCC 25196 Nostoc sp. PCC 7120 Nostoc punctiforme PCC 73102 Novosphingobium aromaticivorans DSM 12444 Bordetella bronchiseptica RB50 Geobacter sulfurreducens PCA Wigglesworthia glossinidia endosymbiont of Glossina brevipalpis Xanthomonas axonopodis pv. citri str. 306 Leptospira interrogans serovar Lai str. 56601 Nitrosomonas europaea ATCC 19718 Chromobacterium violaceum ATCC 12472 Bdellovibrio bacteriovorus HD100 Leptospira interrogans serovar Copenhageni str. Fiocruz L1-130 Thermus thermophilus HB27 Sodalis glossinidius str. 'morsitans' Synechococcus sp. JA-2-3B'a(2-13) Syntrophomonas wolfei subsp. wolfei str. Goettingen Candidatus Ruthia magnifica str. Cm (Calyptogena magnifica) Sorangium cellulosum 'So ce 56' Opitutus terrae PB90-1 Leptospira biflexa serovar Patoc strain 'Patoc 1 (Paris)' Alteromonas macleodii str. 'Deep ecotype' Gemmatimonas aurantiaca T-27 Deferribacter desulfuricans SSM1 Denitrovibrio acetiphilus DSM 12809 Calditerrivibrio nitroreducens DSM 19672 Thermus scotoductus SA-01 Rhodobacter capsulatus SB1003 Pantoea ananatis LMG 20103 Paracoccus denitrificans PD1222 Parvibaculum lavamentivorans DS-1 Pasteurella multocida subsp. multocida str. Pm70 Pectobacterium atrosepticum SCRI1043 Pectobacterium carotovorum subsp. carotovorum PC1 Pedobacter heparinus DSM 2366 Pelobacter carbinolicus DSM 2380 Pelobacter propionicus DSM 2379 Chlorobium luteolum DSM 273 Pelodictyon phaeoclathratiforme BU-1 Persephonella marina EX-H1 Petrotoga mobilis SJ95 Phenylobacterium zucineum HLK1 Photobacterium profundum SS9 Photorhabdus luminescens subsp. laumondii TTO1 Photorhabdus asymbiotica subsp. asymbiotica ATCC 43949 Pirellula staleyi DSM 6068 Planctomyces limnophilus DSM 3776 Polaromonas sp. JS666 Polaromonas naphthalenivorans CJ2 Polynucleobacter necessarius subsp. asymbioticus QLW-P1DMWA-1 Prochlorococcus marinus subsp. marinus str. CCMP1375 Prochlorococcus marinus str. MIT 9313 Prochlorococcus marinus subsp. pastoris str. CCMP1986 Prochlorococcus marinus str. NATL2A Prochlorococcus marinus str. MIT 9312 Prochlorococcus marinus str. AS9601 Prochlorococcus marinus str. MIT 9515 Prochlorococcus marinus str. NATL1A Prochlorococcus marinus str. MIT 9303 Prochlorococcus marinus str. MIT 9301 Prochlorococcus marinus str. MIT 9215 Prochlorococcus marinus str. MIT 9211 Prosthecochloris aestuarii DSM 271 Pseudoalteromonas haloplanktis TAC125 Pseudomonas syringae pv. tomato str. DC3000 Pseudomonas syringae pv. phaseolicola 1448A Pseudomonas syringae pv. syringae B728a Pseudomonas entomophila L48 Pseudomonas fulva 12-X Psychrobacter arcticus 273-4 Psychrobacter cryohalolentis K5 Psychromonas ingrahamii 37 Ralstonia solanacearum GMI1000 Rhizobium etli CFN 42 Rhizobium etli CIAT 652 Rhizobium leguminosarum bv. trifolii WSM1325 Rhodopirellula baltica SH 1 Rhodopseudomonas palustris CGA009 Rhodopseudomonas palustris HaA2 Rhodopseudomonas palustris BisB5 Rhodospirillum centenum SW Rhodothermus marinus DSM 4252 Roseiflexus sp. RS-1 Roseiflexus castenholzii DSM 13941 Roseobacter denitrificans OCh 114 Roseobacter litoralis Och 149 Ruegeria pomeroyi DSS-3 Ruegeria sp. TM1040 Saccharophagus degradans 2-40 Salinibacter ruber DSM 13855 Salmonella enterica subsp. enterica serovar Paratyphi A str. Sebaldella termitidis ATCC 33386 Segniliparus rotundus DSM 44985 Shewanella oneidensis MR-1 Shewanella sp. ANA-3 Shewanella amazonensis SB2B Shewanella sp. W3-18-1 Shewanella baltica OS155 Shewanella loihica PV-4 Shewanella sediminis HAW-EB3 Shewanella pealeana ATCC 700345 Shewanella baltica OS195 Shewanella halifaxensis HAW-EB4 Shewanella woodyi ATCC 51908 Shewanella piezotolerans WP3 Shewanella baltica OS223 Shewanella violacea DSS12 Shigella flexneri 2a str. 301 Shigella boydii Sb227 Shigella boydii CDC 3083-94 Sinorhizobium meliloti 1021 Sinorhizobium medicae WSM419 Sphingobium japonicum UT26S Sphingomonas wittichii RW1 Sphingopyxis alaskensis RB2256 Sulfurihydrogenibium azorense Az-Fu1 Sulfurimonas denitrificans DSM 1251 Synechococcus sp. WH 8102 Synechococcus sp. CC9902 Synechococcus sp. JA-3-3Ab Synechococcus sp. CC9311 Synechococcus sp. WH 7803 Synechococcus sp. RCC307 Synechococcus sp. PCC 7002 Taylorella equigenitalis MCE9 Teredinibacter turnerae T7901 Thermocrinis albus DSM 14484 Thermomicrobium roseum DSM 5159 Thermoplasma volcanium GSS1 Thermosipho melanesiensis BI429 Thermosipho africanus TCF52B Thermotoga petrophila RKU-1 Thermotoga sp. RQ2 Thermotoga neapolitana DSM 4359 Thioalkalivibrio sp. K90mix Thiobacillus denitrificans ATCC 25259 Tolumonas auensis DSM 9187 Treponema brennaborense DSM 12168 Variovorax paradoxus EPS Verminephrobacter eiseniae EF01-2 Vibrio vulnificus CMCP6 Vibrio vulnificus YJ016 Vibrio splendidus LGP32 Weeksella virosa DSM 16922 Xanthobacter autotrophicus Py2 Xanthomonas oryzae pv. oryzae KACC10331 Xanthomonas campestris pv. vesicatoria str. 85-10 Xanthomonas oryzae pv. oryzae PXO99A Xenorhabdus bovienii SS-2004 Xenorhabdus nematophila ATCC 19061 Xylella fastidiosa 9a5c Xylella fastidiosa Temecula1 Xylella fastidiosa M23 Zunongwangia profunda SM-A87 Zymomonas mobilis subsp. pomaceae ATCC 29192 Sphingobacterium paucimobilis HER1398 Neisseria meningitidis serogroup C Atlantibacter hermannii NBRC 105704 Klebsiella michiganensis KCTC 1686 Chania multitudinisentens RB-25 Hungatella hathewayi DSM 13479 Veillonella seminalis ACS-216-V-Col6b
Reductive acetyl-CoA pathway (Wood-Ljungdahl pathway)

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018078	Tetrahydrofolic acid	Glycineamideribotide	Formate-dependent phosphoribosylglycinamide formyltransferase	Transfer of a formyl group	PathBank	31602464
MMDBr0018079	5,10-Methenyltetrahydrofolic acid	N5-Formyl-THF	Aminomethyltransferase	Methylation	PathBank	31602464
MMDBr0019500	5,10-Methylene-THF	5,10-Methenyltetrahydrofolic acid	C-1-tetrahydrofolate synthase, mitochondrial	Synthesis	PathBank	31602464
MMDBr0019501	5,10-Methenyltetrahydrofolic acid	N10-Formyl-THF	C-1-tetrahydrofolate synthase, mitochondrial	Synthesis	PathBank	31602464
MMDBr0019781	Tetrahydrofolic acid	Glycineamideribotide	Phosphoribosylaminoimidazole carboxylase	Carboxylation	PathBank	31602464
MMDBr0019782	5,10-Methenyltetrahydrofolic acid	N5-Formyl-THF	Aminomethyltransferase, mitochondrial	Methylation	PathBank	31602464
MMDBr0020670	N10-Formyl-THF	5,10-Methenyltetrahydrofolic acid	Bifunctional protein FolD		PathBank	31602464
MMDBr0020672	5,10-Methenyltetrahydrofolic acid	5,10-Methylene-THF	Unknown Protein		PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	389	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	181	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	128	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	2	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	4		Metabolic reconstruction
Bacteria/Eubacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0001354

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022573

KNApSAcK ID

Not Available

Chemspider ID

559356

KEGG Compound ID

C00445

BioCyc ID

Not Available

BiGG ID

34999

Wikipedia Link

5,10-Methenyltetrahydrofolate

METLIN ID

6185

PubChem Compound

135450599

PDB ID

Not Available

ChEBI ID

15636

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Jahansouz H, Scherubel DM, Himes RH: Formylation of tetrahydrofolate by formyl phosphate. FEBS Lett. 1990 Mar 26;262(2):366-8. doi: 10.1016/0014-5793(90)80231-7. [PubMed:2335221 ]
Telegina TA, Liudnikova TA, Zemskova IuL, Sviridov EA, Kritskii MS: [Tolerance of 5,10-methenyltetrahydrofolate to ultraviolet radiation]. Prikl Biokhim Mikrobiol. 2005 May-Jun;41(3):315-23. [PubMed:15977793 ]
Field MS, Szebenyi DM, Stover PJ: Regulation of de novo purine biosynthesis by methenyltetrahydrofolate synthetase in neuroblastoma. J Biol Chem. 2006 Feb 17;281(7):4215-21. doi: 10.1074/jbc.M510624200. Epub 2005 Dec 19. [PubMed:16365037 ]
Moldt J, Pokorny R, Orth C, Linne U, Geisselbrecht Y, Marahiel MA, Essen LO, Batschauer A: Photoreduction of the folate cofactor in members of the photolyase family. J Biol Chem. 2009 Aug 7;284(32):21670-83. doi: 10.1074/jbc.M109.018697. Epub 2009 Jun 16. [PubMed:19531478 ]
Kruszyna L, Lianeri M, Rydzanicz M, Gajecka M, Szyfter K, Jagodzinski PP: Polymorphic variants of folate metabolism genes and the risk of laryngeal cancer. Mol Biol Rep. 2010 Jan;37(1):241-7. doi: 10.1007/s11033-009-9643-y. Epub 2009 Aug 1. [PubMed:19649727 ]
Kirsch SH, Knapp JP, Herrmann W, Obeid R: Quantification of key folate forms in serum using stable-isotope dilution ultra performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Jan 1;878(1):68-75. doi: 10.1016/j.jchromb.2009.11.021. [PubMed:19959403 ]
Kariluoto S, Edelmann M, Herranen M, Lampi AM, Shmelev A, Salovaara H, Korhola M, Piironen V: Production of folate by bacteria isolated from oat bran. Int J Food Microbiol. 2010 Sep 30;143(1-2):41-7. doi: 10.1016/j.ijfoodmicro.2010.07.026. Epub 2010 Aug 11. [PubMed:20708290 ]
Knock E, Deng L, Krupenko N, Mohan RD, Wu Q, Leclerc D, Gupta S, Elmore CL, Kruger W, Tini M, Rozen R: Susceptibility to intestinal tumorigenesis in folate-deficient mice may be influenced by variation in one-carbon metabolism and DNA repair. J Nutr Biochem. 2011 Nov;22(11):1022-9. doi: 10.1016/j.jnutbio.2010.07.015. Epub 2010 Dec 28. [PubMed:21193302 ]
Ogwang S, Nguyen HT, Sherman M, Bajaksouzian S, Jacobs MR, Boom WH, Zhang GF, Nguyen L: Bacterial conversion of folinic acid is required for antifolate resistance. J Biol Chem. 2011 Apr 29;286(17):15377-90. doi: 10.1074/jbc.M111.231076. Epub 2011 Mar 3. [PubMed:21372133 ]
Lin CJ, Wen MJ, Hung YJ, Pei D, Kuo SW, Hsieh CH: The impact of 5,10-methenyltetrahydrofolate synthetase polymorphism on diabetic nephropathy in the Taiwanese population. Genet Test Mol Biomarkers. 2012 Feb;16(2):142-5. doi: 10.1089/gtmb.2011.0050. Epub 2011 Sep 6. [PubMed:21895484 ]
Oberpichler I, Pierik AJ, Wesslowski J, Pokorny R, Rosen R, Vugman M, Zhang F, Neubauer O, Ron EZ, Batschauer A, Lamparter T: A photolyase-like protein from Agrobacterium tumefaciens with an iron-sulfur cluster. PLoS One. 2011;6(10):e26775. doi: 10.1371/journal.pone.0026775. Epub 2011 Oct 31. [PubMed:22066008 ]
Eadsforth TC, Cameron S, Hunter WN: The crystal structure of Leishmania major N(5),N(10)-methylenetetrahydrofolate dehydrogenase/cyclohydrolase and assessment of a potential drug target. Mol Biochem Parasitol. 2012 Feb;181(2):178-85. doi: 10.1016/j.molbiopara.2011.11.004. Epub 2011 Nov 15. [PubMed:22108435 ]
Watkins D, Rosenblatt DS: Update and new concepts in vitamin responsive disorders of folate transport and metabolism. J Inherit Metab Dis. 2012 Jul;35(4):665-70. doi: 10.1007/s10545-011-9418-1. Epub 2011 Nov 23. [PubMed:22108709 ]
Selby CP, Sancar A: The second chromophore in Drosophila photolyase/cryptochrome family photoreceptors. Biochemistry. 2012 Jan 10;51(1):167-71. doi: 10.1021/bi201536w. Epub 2011 Dec 27. [PubMed:22175817 ]
Field MS, Anderson DD, Stover PJ: Mthfs is an Essential Gene in Mice and a Component of the Purinosome. Front Genet. 2011 Jun 20;2:36. doi: 10.3389/fgene.2011.00036. eCollection 2011. [PubMed:22303332 ]
Tolley M, Bickford L, Clare K, Johann TW: Investigations of amino acids in the ATP binding site of 5,10-methenyltetrahydrofolate synthetase. Protein J. 2012 Aug;31(6):519-28. doi: 10.1007/s10930-012-9428-3. [PubMed:22773193 ]
Upadhyay V, Demmer U, Warkentin E, Moll J, Shima S, Ermler U: Structure and catalytic mechanism of N(5),N(10)-methenyl-tetrahydromethanopterin cyclohydrolase. Biochemistry. 2012 Oct 23;51(42):8435-43. doi: 10.1021/bi300777k. Epub 2012 Oct 8. [PubMed:23013430 ]
Wijaya IM, Zhang Y, Iwata T, Yamamoto J, Hitomi K, Iwai S, Getzoff ED, Kandori H: Detection of distinct alpha-helical rearrangements of cyclobutane pyrimidine dimer photolyase upon substrate binding by Fourier transform infrared spectroscopy. Biochemistry. 2013 Feb 12;52(6):1019-27. doi: 10.1021/bi3016179. Epub 2013 Jan 30. [PubMed:23331252 ]

Showing metabocard for 5,10-Methenyltetrahydrofolic acid (MMDBc0031998)

MOL for #<Metabolite:0x00007f9ad07ed868>

3D MOL for #<Metabolite:0x00007f9ad07ed868>

3D SDF for #<Metabolite:0x00007f9ad07ed868>

3D-SDF for #<Metabolite:0x00007f9ad07ed868>

PDB for #<Metabolite:0x00007f9ad07ed868>

3D PDB for #<Metabolite:0x00007f9ad07ed868>

SMILES for #<Metabolite:0x00007f9ad07ed868>

INCHI for #<Metabolite:0x00007f9ad07ed868>

Structure for #<Metabolite:0x00007f9ad07ed868>

3D Structure for #<Metabolite:0x00007f9ad07ed868>