MiMeDB: Showing metabocard for N5-methyl--tetrahydropteroyl tri-L-glutamate (MMDBc0032164)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:05:05 UTC

Update Date

2022-08-31 18:31:03 UTC

Metabolite ID

MMDBc0032164

Metabolite Identification

Common Name

N5-methyl--tetrahydropteroyl tri-L-glutamate

Description

N5-methyl--tetrahydropteroyl tri-L-glutamate is an intermediate in L-methionine biosynthesis I and S-adenosyl-L-methionine cycle I in E.coli. In both pathways, it is a substrate for the enzyme cobalamin-dependent methionine synthase which catalyzes the reaction L-homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate ‚Üí L-methionine + tetrahydropteroyl tri-L-glutamate (BioCyc compound: CPD-1302).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533005151518332D          

 51 53  0  0  0  0            999 V2000
   -6.4302   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7157   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7157   -2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.6812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8591   -2.6812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5736   -2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5736   -1.4437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8591   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8591   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -2.6812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.6812    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.4437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -0.2062    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157    1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.6812    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.7157    2.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    0.2062    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.0012    2.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
  6 12  2  0  0  0  0
  8 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 23 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 31 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 39 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 37 48  2  0  0  0  0
 29 49  2  0  0  0  0
 19 50  1  0  0  0  0
 50 51  2  0  0  0  0
 16 51  1  0  0  0  0
M  CHG  4  25  -1  33  -1  41  -1  47  -1
M  END


  Mrv1533005151518332D          

 51 53  0  0  0  0            999 V2000
   -6.4302   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7157   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7157   -2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.6812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8591   -2.6812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5736   -2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5736   -1.4437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8591   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8591   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -2.6812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.6812    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.4437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -0.2062    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157    1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.6812    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.7157    2.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    0.2062    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.0012    2.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
  6 12  2  0  0  0  0
  8 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 23 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 31 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 39 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 37 48  2  0  0  0  0
 29 49  2  0  0  0  0
 19 50  1  0  0  0  0
 50 51  2  0  0  0  0
 16 51  1  0  0  0  0
M  CHG  4  25  -1  33  -1  41  -1  47  -1
M  END
> <DATABASE_ID>
MMDBc0032164

> <DATABASE_NAME>
MIME

> <SMILES>
CN1C(CNC2=CC=C(C=C2)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC([O-])=O)C([O-])=O)C([O-])=O)C([O-])=O)CNC2=C1C(=O)NC(N)=N2

> <INCHI_IDENTIFIER>
InChI=1S/C30H39N9O12/c1-39-16(13-33-24-23(39)26(45)38-30(31)37-24)12-32-15-4-2-14(3-5-15)25(44)36-19(29(50)51)7-10-21(41)34-17(27(46)47)6-9-20(40)35-18(28(48)49)8-11-22(42)43/h2-5,16-19,32H,6-13H2,1H3,(H,34,41)(H,35,40)(H,36,44)(H,42,43)(H,46,47)(H,48,49)(H,50,51)(H4,31,33,37,38,45)/p-4

> <INCHI_KEY>
HVRNKDVLFAVCJF-UHFFFAOYSA-J

> <FORMULA>
C30H35N9O12

> <MOLECULAR_WEIGHT>
713.663

> <EXACT_MASS>
713.242711923

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
69.30117173122171

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{4-[(4-{[(2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxylatobutanamido}-4-carboxylatobutanamido)pentanedioate

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-3.520613300076094

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.5127503209866195

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6822465659634904

> <JCHEM_PKA_STRONGEST_BASIC>
3.139884793816262

> <JCHEM_POLAR_SURFACE_AREA>
342.59999999999997

> <JCHEM_REFRACTIVITY>
226.4053000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{4-[(4-{[(2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxylatobutanamido}-4-carboxylatobutanamido)pentanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-15         0                                  
HETATM    1  C   UNK     0     -12.003  -0.385   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0     -12.003  -1.925   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0     -10.669  -2.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669  -4.235   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0     -12.003  -5.005   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0     -13.337  -4.235   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0     -14.670  -5.005   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0     -16.004  -4.235   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0     -16.004  -2.695   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0     -14.670  -1.925   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -14.670  -0.385   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -13.337  -2.695   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0     -17.338  -5.005   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -9.336  -1.925   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -9.336  -0.385   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -8.002   0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   1.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668   2.695   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001   2.695   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001   4.235   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      -2.667   1.925   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -1.334   2.695   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334   4.235   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000   5.005   0.000  0.00  0.00           O-1
HETATM   26  O   UNK     0      -2.667   5.005   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000   1.925   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   2.695   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   1.925   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       4.001   2.695   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       5.335   1.925   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335   0.385   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.668  -0.385   0.000  0.00  0.00           O-1
HETATM   34  O   UNK     0       4.001  -0.385   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.668   2.695   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002   1.925   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.336   2.695   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      10.669   1.925   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      12.003   2.695   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.003   4.235   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      13.337   5.005   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0      10.669   5.005   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      13.337   1.925   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      14.670   2.695   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.004   1.925   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      17.338   2.695   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      16.004   0.385   0.000  0.00  0.00           O-1
HETATM   48  O   UNK     0       9.336   4.235   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       2.667   0.385   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -5.335   0.385   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -6.668  -0.385   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    2    6                                                  
CONECT   13    8                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   51                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   50                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   49                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   31   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   48                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   43                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   39   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   37                                                            
CONECT   49   29                                                            
CONECT   50   19   51                                                       
CONECT   51   50   16                                                       
MASTER        0    0    0    0    0    0    0    0   51    0  106    0
END

Synonyms

Value	Source
N5-Methyl--tetrahydropteroyl tri-L-glutamic acid	Generator

Molecular Formula

C₃₀H₃₅N₉O₁₂

Average Mass

713.663

Monoisotopic Mass

713.242711923

IUPAC Name

2-(4-{4-[(4-{[(2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxylatobutanamido}-4-carboxylatobutanamido)pentanedioate

Traditional Name

2-(4-{4-[(4-{[(2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxylatobutanamido}-4-carboxylatobutanamido)pentanedioate

CAS Registry Number

Not Available

SMILES

CN1C(CNC2=CC=C(C=C2)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC([O-])=O)C([O-])=O)C([O-])=O)C([O-])=O)CNC2=C1C(=O)NC(N)=N2

InChI Identifier

InChI=1S/C30H39N9O12/c1-39-16(13-33-24-23(39)26(45)38-30(31)37-24)12-32-15-4-2-14(3-5-15)25(44)36-19(29(50)51)7-10-21(41)34-17(27(46)47)6-9-20(40)35-18(28(48)49)8-11-22(42)43/h2-5,16-19,32H,6-13H2,1H3,(H,34,41)(H,35,40)(H,36,44)(H,42,43)(H,46,47)(H,48,49)(H,50,51)(H4,31,33,37,38,45)/p-4

InChI Key

HVRNKDVLFAVCJF-UHFFFAOYSA-J

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Pyrimidone
Aminopyrimidine
Pyrimidine
Alkyl phosphate
Phosphoric acid ester
Oxane
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Vinylogous amide
Azole
Imidazole
Oxolane
Heteroaromatic compound
Secondary alcohol
1,2-diol
Polyol
Organoheterocyclic compound
Azacycle
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Primary amine
Alcohol
Organooxygen compound
Organonitrogen compound
Amine
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a GDP-sugar (GUANOSINE_DIPHOSPHATE_FUCOSE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.95 g/L	ALOGPS
logP	0.11	ALOGPS
logP	-3.5	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	2.68	ChemAxon
pKa (Strongest Basic)	3.14	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	342.6 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	226.41 m³·mol⁻¹	ChemAxon
Polarizability	69.3 Å³	ChemAxon
Number of Rings	3	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-12c56169fecdd9f1abda	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000004900-74d9c3f43e245acb61d1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9220003200-ae49c32b2aa0b39c52fc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000900-8aa96c83c5c265ff009a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03k9-2000002900-364f6ba4e7a9e5066a1e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100001000-5b24b298a89419aedc5d	2015-09-15	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	573.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	240.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	422.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	513.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	290.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	185.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1524.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	711.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	392.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	174.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	319.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	157.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	120.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	363.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	427.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	86.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	305.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1338.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	821.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_1	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	1929.07
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_2	CN1C2=C(N=C(N)[NH]C2=O)NCC1CN(C1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1)[Si](C)(C)C	standard non polar	2025-10-24	2079.47
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_3	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1	standard non polar	2025-10-24	1732.58
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_4	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1	standard non polar	2025-10-24	2312.04
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_5	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	610.372
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_6	CN1C2=C(N=C(N)[NH]C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	2328.2
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_7	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	1642.05
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_8	CN1C2=C(N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	1264.2
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_9	CN1C2=C(N=C(N[Si](C)(C)C)N([Si](C)(C)C)C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	678.991
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_10	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	1548.62
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_11	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)NCC1CN(C1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1)[Si](C)(C)C	standard non polar	2025-10-24	2519.04
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_12	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)NCC1CNC1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1	standard non polar	2025-10-24	1620.91
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_13	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1	standard non polar	2025-10-24	824.313
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_14	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	1458.93
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_15	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)NCC1CN(C1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1681.05
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_16	CN1C2=C(N=C(N)[NH]C2=O)N([Si](C)(C)C)CC1CN(C1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1)[Si](C)(C)C	standard non polar	2025-10-24	3243.89
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_17	CN1C2=C(N=C(N)[NH]C2=O)NCC1CN(C1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	2534.66
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_18	CN1C2=C(N=C(N)[NH]C2=O)NCC1CN(C1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1999.5
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_19	CN1C2=C(N=C(N)[NH]C2=O)NCC1CN(C1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1427.26
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_20	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)NCC1CNC1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1	standard non polar	2025-10-24	2890.97
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_21	CN1C2=C(N=C(N)[NH]C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1	standard non polar	2025-10-24	1071.55
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_22	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)N(C(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C=C1	standard non polar	2025-10-24	2170.21
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_23	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1	standard non polar	2025-10-24	2020.43
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_24	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1	standard non polar	2025-10-24	1444.38
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_25	CN1C2=C(N=C(N)[NH]C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1	standard non polar	2025-10-24	3670.37
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_26	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1	standard non polar	2025-10-24	726.535
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_27	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	662.924
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_28	CN1C2=C(N=C(N)[NH]C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	262.908
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_29	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard non polar	2025-10-24	1391.59
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_1	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	3105.85
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_2	CN1C2=C(N=C(N)[NH]C2=O)NCC1CN(C1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1)[Si](C)(C)C	standard polar	2025-10-24	3158.97
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_3	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1	standard polar	2025-10-24	1499.28
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_4	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1	standard polar	2025-10-24	2834.35
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_5	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	1675.05
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_6	CN1C2=C(N=C(N)[NH]C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	2672.01
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_7	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	1265.89
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_8	CN1C2=C(N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	-455.267
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_9	CN1C2=C(N=C(N[Si](C)(C)C)N([Si](C)(C)C)C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	4002.06
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_10	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	2454.99
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_11	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)NCC1CN(C1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1)[Si](C)(C)C	standard polar	2025-10-24	2490.41
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_12	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)NCC1CNC1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1	standard polar	2025-10-24	2242.73
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_13	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1	standard polar	2025-10-24	2317.62
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_14	CN1C2=C(N=C(N[Si](C)(C)C)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	3288.22
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_15	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)NCC1CN(C1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1)[Si](C)(C)C	standard polar	2025-10-24	2761.26
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_16	CN1C2=C(N=C(N)[NH]C2=O)N([Si](C)(C)C)CC1CN(C1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1)[Si](C)(C)C	standard polar	2025-10-24	2352.11
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_17	CN1C2=C(N=C(N)[NH]C2=O)NCC1CN(C1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1)[Si](C)(C)C	standard polar	2025-10-24	2843.08
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_18	CN1C2=C(N=C(N)[NH]C2=O)NCC1CN(C1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1)[Si](C)(C)C	standard polar	2025-10-24	3779.53
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_19	CN1C2=C(N=C(N)[NH]C2=O)NCC1CN(C1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])C=C1)[Si](C)(C)C	standard polar	2025-10-24	1154.27
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_20	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)NCC1CNC1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1	standard polar	2025-10-24	1436.12
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_21	CN1C2=C(N=C(N)[NH]C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1	standard polar	2025-10-24	1310.08
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_22	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)N(C(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C=C1	standard polar	2025-10-24	2231.47
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_23	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)N(C(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C=C1	standard polar	2025-10-24	2458.33
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_24	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1	standard polar	2025-10-24	319.296
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_25	CN1C2=C(N=C(N)[NH]C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1	standard polar	2025-10-24	1091.58
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_26	CN1C2=C(N=C(N)[NH]C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)N(C(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C=C1	standard polar	2025-10-24	2759.36
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_27	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)NCC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	1721.6
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_28	CN1C2=C(N=C(N)[NH]C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)N(C(CCC(=O)[O-])C(=O)[O-])[Si](C)(C)C)C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	3815.34
Gas Chromatography	N5-methyl--tetrahydropteroyl tri-L-glutamate_TMS_29	CN1C2=C(N=C(N)N([Si](C)(C)C)C2=O)N([Si](C)(C)C)CC1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(=O)[O-])C(=O)[O-])C(=O)[O-])C(=O)[O-])C=C1	standard polar	2025-10-24	2144.58

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Name	SMPDB/PathBank	Species
Methionine Biosynthesis		Escherichia coli Escherichia coli SMS-3-5 Escherichia coli UTI89 Escherichia coli 55989 Escherichia coli SE11 Escherichia coli CFT073 Bacillus subtilis Klebsiella pneumoniae Bacillus cereus Bacillus amyloliquefaciens Streptococcus pneumoniae Salmonella enterica Streptococcus pneumoniae TIGR4 Shewanella denitrificans OS217 Bacillus cereus AH187 (F4810/72) Bacillus halodurans C-125 Alkalihalobacillus pseudofirmus OF4 Bacillus timonensis 10403023 Streptococcus salivarius lactobacillus vaginalis Citrobacter koseri Proteus mirabilis Shigella boydii Shigella dysenteriae Shigella flexneri Shigella sonnei Aeromonas hydrophila Vibrio vulnificus Leuconostoc mesenteroides Streptococcus gordonii Streptococcus oralis Streptococcus sanguinis Streptococcus mutans Streptococcus equinus Bacillus licheniformis Priestia megaterium Bacillus mycoides Bacillus pumilus Bacillus thuringiensis Lactobacillus helveticus Lactobacillus plantarum Lactobacillus coryniformis Thermotoga neapolitana Streptococcus cristatus Sodalis glossinidius Streptococcus peroris Enterobacter cancerogenus Bacillus clausii Bacillus pseudofirmus Citrobacter youngae Leuconostoc kimchii Streptococcus lutetiensis Shewanella denitrificans Escherichia albertii Lactobacillus antri Streptococcus pseudopneumoniae Streptococcus gallolyticus Gemella sanguinis Klebsiella variicola Lactobacillus rhamnosus Lactobacillus ruminis Lactococcus lactis Streptococcus parasanguinis Streptococcus suis Streptococcus thermophiles Gemella haemolysans Aeromonas hydrophila subsp. hydrophila ATCC 7966 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 Citrobacter koseri ATCC BAA-895 Cronobacter sakazakii ATCC BAA-894 Enterobacter cloacae subsp. cloacae ATCC 13047 Escherichia coli E24377A Escherichia coli O127:H6 str. E2348/69 Escherichia coli UMN026 Escherichia fergusonii ATCC 35469 Escherichia coli ED1a Escherichia coli IAI39 Klebsiella pneumoniae subsp. pneumoniae MGH 78578 Lactobacillus plantarum WCFS1 Lactobacillus casei ATCC 334 Lactobacillus helveticus DPC 4571 Lactococcus lactis subsp. lactis Il1403 Lactococcus lactis subsp. cremoris MG1363 Leuconostoc mesenteroides subsp. mesenteroides ATCC 8293 Lysinibacillus sphaericus C3-41 Escherichia coli 042 Edwardsiella tarda FL6-60 Proteus mirabilis HI4320 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 Streptococcus mutans UA159 Streptococcus thermophilus LMG 18311 Streptococcus pneumoniae D39 Streptococcus sanguinis SK36 Streptococcus gordonii str. Challis substr. CH1 Streptococcus pneumoniae Hungary19A-6 Streptococcus pneumoniae JJA Streptococcus oralis Uo5 Vibrio parahaemolyticus RIMD 2210633 Yersinia enterocolitica subsp. enterocolitica 8081 Yersinia pseudotuberculosis IP 31758 Prevotella denticola Aeromonas caviae Aeromonas media Aeromonas veronii 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 Grimontia hollisae CIP 101886 Vibrio fluvialis Vibrio fluvialis PG41 Vibrio parahaemolyticus Vibrio mimicus Olsenella profusa F0195 Bacillus altitudinis Bacillus infantis NRRL B-14911 Bacillus firmus DS1 Lysinibacillus sphaericus Paenibacillus lactis 154 Gemella haemolysans ATCC 10379 Enterococcus asini ATCC 700915 Enterococcus caccae ATCC BAA-1240 Lactobacillus paracasei subsp. paracasei 8700:2 Lactobacillus rhamnosus LMS2-1 Lactobacillus hilgardii DSM 20176 = ATCC 8290 Lactobacillus antri DSM 16041 Lactobacillus vaginalis DSM 5837 = ATCC 49540 Lactobacillus coryniformis subsp. coryniformis CECT 5711 Streptococcus australis ATCC 700641 Streptococcus equinus ATCC 9812 Streptococcus infantis ATCC 700779 Streptococcus lutetiensis 033 Streptococcus vestibularis F0396 Lachnospira multipara [Clostridium] spiroforme DSM 1552 Kandleria vitulina DSM 20405 Vibrio cholerae M66-2 Vibrio cholerae O1 biovar El Tor str. N16961 Shewanella frigidimarina NCIMB 400 Bacillus cytotoxicus NVH 391-98 Lactobacillus ruminis ATCC 27782 Streptococcus mitis B6 Streptococcus parasanguinis ATCC 15912 Streptococcus parasanguinis FW213 Streptococcus pasteurianus ATCC 43144 Streptococcus suis GZ1 Leuconostoc kimchii IMSNU 11154 Macrococcus caseolyticus JCSC5402 Staphylococcus carnosus subsp. carnosus TM300 Streptococcus suis BM407 Streptococcus gallolyticus UCN34 Holdemanella biformis DSM 3989 Klebsiella aerogenes KCTC 2190 Aeromonas salmonicida subsp. salmonicida A449 Vibrio fischeri MJ11 Burkholderia phymatum STM815 Citrobacter rodentium ICC168 Colwellia psychrerythraea 34H Cronobacter turicensis z3032 Dickeya dadantii Ech703 Dickeya zeae Ech1591 Dickeya dadantii Ech586 Dickeya dadantii 3937 Edwardsiella ictaluri 93-146 Enterobacter sp. 638 Enterobacter cloacae SCF1 Erwinia tasmaniensis Et1/99 Erwinia amylovora CFBP1430 Erwinia billingiae Eb661 Klebsiella pneumoniae 342 Sodalis glossinidius str. 'morsitans' Alteromonas macleodii str. 'Deep ecotype' Pantoea ananatis LMG 20103 Paracoccus denitrificans PD1222 Pectobacterium atrosepticum SCRI1043 Pectobacterium carotovorum subsp. carotovorum PC1 Pedobacter heparinus DSM 2366 Photobacterium profundum SS9 Photorhabdus luminescens subsp. laumondii TTO1 Photorhabdus asymbiotica subsp. asymbiotica ATCC 43949 Pseudoalteromonas haloplanktis TAC125 Psychromonas ingrahamii 37 Salmonella enterica subsp. enterica serovar Paratyphi A str. 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 woodyi ATCC 51908 Shewanella piezotolerans WP3 Shewanella violacea DSS12 Shigella flexneri 2a str. 301 Shigella boydii Sb227 Shigella boydii CDC 3083-94 Sphingomonas wittichii RW1 Thermotoga petrophila RKU-1 Thermotoga sp. RQ2 Thermotoga neapolitana DSM 4359 Tolumonas auensis DSM 9187 Vibrio vulnificus CMCP6 Vibrio vulnificus YJ016 Vibrio splendidus LGP32 Xenorhabdus bovienii SS-2004 Xenorhabdus nematophila ATCC 19061 Sphingobacterium paucimobilis HER1398 Atlantibacter hermannii NBRC 105704 Klebsiella michiganensis KCTC 1686 Chania multitudinisentens RB-25

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
MMDBr0018277	Homocysteine	L-Methionine	Methionine synthase	Synthesis	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/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal	Unknown

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for N5-methyl--tetrahydropteroyl tri-L-glutamate (MMDBc0032164)

MOL for #<Metabolite:0x00007f9ab2875e70>

3D MOL for #<Metabolite:0x00007f9ab2875e70>

3D SDF for #<Metabolite:0x00007f9ab2875e70>

3D-SDF for #<Metabolite:0x00007f9ab2875e70>

PDB for #<Metabolite:0x00007f9ab2875e70>

3D PDB for #<Metabolite:0x00007f9ab2875e70>

SMILES for #<Metabolite:0x00007f9ab2875e70>

INCHI for #<Metabolite:0x00007f9ab2875e70>

Structure for #<Metabolite:0x00007f9ab2875e70>

3D Structure for #<Metabolite:0x00007f9ab2875e70>