MiMeDB: Showing metabocard for (6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid (MMDBc0054976)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:38:58 UTC

Update Date

2025-10-07 16:08:49 UTC

Metabolite ID

MMDBc0054976

Metabolite Identification

Common Name

(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid

Description

(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid is a member of the folate chemical class. There is limited literature available on this metabolite, indicating that further research may be necessary to fully understand its biological significance and potential applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221382D          

 35 38  0  0  1  0            999 V2000
   -3.4722    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1867    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7577    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4722    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0445    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7590    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    2.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2896    1.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570    3.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1867    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7577    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375    2.5315    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3301    0.6039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4735    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375    3.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    3.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9011    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500    4.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3301   -0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    5.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    6.1038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    3.2459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6156    1.0164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    4.6749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375    5.3894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    2.2539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500    3.2459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1880    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4735    1.8414    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -4.9011   -0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750    4.6749    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.6156   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0445   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3250    3.2459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0445    0.1914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  5  1  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 16 15  2  0  0  0  0
 17 10  1  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 21 20  2  0  0  0  0
 22  7  1  0  0  0  0
 22 16  1  0  0  0  0
 13 23  1  1  0  0  0
 23 17  1  0  0  0  0
 24 16  1  0  0  0  0
 24 20  1  0  0  0  0
 25 18  2  0  0  0  0
 25 20  1  0  0  0  0
 26  8  1  0  0  0  0
 26  9  1  0  0  0  0
 26 11  1  0  0  0  0
 27  9  1  0  0  0  0
 27 12  1  0  0  0  0
 27 15  1  0  0  0  0
 28 14  2  0  0  0  0
 29 14  1  0  0  0  0
 30 17  2  0  0  0  0
 31 18  1  0  0  0  0
 32 19  2  0  0  0  0
 33 19  1  0  0  0  0
 12 34  1  1  0  0  0
 13 35  1  1  0  0  0
M  CHG  2  29  -1  31  -1
M  END


  Mrv1652306172221382D          

 35 38  0  0  1  0            999 V2000
   -3.4722    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1867    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7577    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4722    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0445    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7590    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    2.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2896    1.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570    3.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1867    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7577    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375    2.5315    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3301    0.6039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4735    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375    3.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    3.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9011    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500    4.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3301   -0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    5.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    6.1038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    3.2459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6156    1.0164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    4.6749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375    5.3894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    2.2539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500    3.2459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1880    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4735    1.8414    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -4.9011   -0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750    4.6749    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.6156   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0445   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3250    3.2459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0445    0.1914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  5  1  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 16 15  2  0  0  0  0
 17 10  1  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 21 20  2  0  0  0  0
 22  7  1  0  0  0  0
 22 16  1  0  0  0  0
 13 23  1  1  0  0  0
 23 17  1  0  0  0  0
 24 16  1  0  0  0  0
 24 20  1  0  0  0  0
 25 18  2  0  0  0  0
 25 20  1  0  0  0  0
 26  8  1  0  0  0  0
 26  9  1  0  0  0  0
 26 11  1  0  0  0  0
 27  9  1  0  0  0  0
 27 12  1  0  0  0  0
 27 15  1  0  0  0  0
 28 14  2  0  0  0  0
 29 14  1  0  0  0  0
 30 17  2  0  0  0  0
 31 18  1  0  0  0  0
 32 19  2  0  0  0  0
 33 19  1  0  0  0  0
 12 34  1  1  0  0  0
 13 35  1  1  0  0  0
M  CHG  2  29  -1  31  -1
M  END
> <DATABASE_ID>
MMDBc0054976

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](CCC([O-])=O)(NC(=O)C1=CC=C(C=C1)N1CN2C3=C(NC[C@]2([H])C1)NC(=N)N=C3[O-])C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N7O6/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/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/p-2/t12-,13+/m1/s1

> <INCHI_KEY>
QYNUQALWYRSVHF-OLZOCXBDSA-L

> <FORMULA>
C20H21N7O6

> <MOLECULAR_WEIGHT>
455.432

> <EXACT_MASS>
455.156428584

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.02931468055887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-({4-[(6aR)-3-imino-1-oxido-3H,4H,5H,6H,6aH,7H,8H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)-4-carboxybutanoate

> <JCHEM_LOGP>
-2.5554683402543046

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.8086133308206467

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.005887206521458

> <JCHEM_PKA_STRONGEST_BASIC>
5.611442082182131

> <JCHEM_POLAR_SURFACE_AREA>
196.33999999999997

> <JCHEM_REFRACTIVITY>
156.15850000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-({4-[(6aR)-3-imino-1-oxido-4H,5H,6H,6aH,7H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)-4-carboxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -6.481   1.127   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.815   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.148   1.897   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.481   4.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.150   1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -14.483   1.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.163   4.725   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.407   3.581   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.653   5.739   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.815   1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.148   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.377   4.725   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.816   1.127   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -15.817   1.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.377   7.393   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.163   7.393   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.149   1.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.147   8.726   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -11.816  -0.413   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.163  10.060   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       0.933  11.394   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       0.933   6.059   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0     -10.482   1.897   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       0.933   8.726   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      -1.377  10.060   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      -3.814   4.207   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      -2.147   6.059   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0     -17.151   1.127   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0     -15.817   3.437   0.000  0.00  0.00           O-1
HETATM   30  O   UNK     0      -9.149  -0.413   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -3.687   8.726   0.000  0.00  0.00           O-1
HETATM   32  O   UNK     0     -10.482  -1.183   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -13.150  -1.183   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      -0.607   6.059   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0     -13.150   0.357   0.000  0.00  0.00           H+0
CONECT    1    3   10                                                       
CONECT    2    4   10                                                       
CONECT    3    1   11                                                       
CONECT    4    2   11                                                       
CONECT    5    6   13                                                       
CONECT    6    5   14                                                       
CONECT    7   12   22                                                       
CONECT    8   12   26                                                       
CONECT    9   26   27                                                       
CONECT   10    1    2   17                                                  
CONECT   11    3    4   26                                                  
CONECT   12    7    8   27   34                                             
CONECT   13    5   19   23   35                                             
CONECT   14    6   28   29                                                  
CONECT   15   16   18   27                                                  
CONECT   16   15   22   24                                                  
CONECT   17   10   23   30                                                  
CONECT   18   15   25   31                                                  
CONECT   19   13   32   33                                                  
CONECT   20   21   24   25                                                  
CONECT   21   20                                                            
CONECT   22    7   16                                                       
CONECT   23   13   17                                                       
CONECT   24   16   20                                                       
CONECT   25   18   20                                                       
CONECT   26    8    9   11                                                  
CONECT   27    9   12   15                                                  
CONECT   28   14                                                            
CONECT   29   14                                                            
CONECT   30   17                                                            
CONECT   31   18                                                            
CONECT   32   19                                                            
CONECT   33   19                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

Synonyms

Value	Source
(6R)-5,10-CH2-H4Folate	ChEBI
(6R)-5,10-Methylene-5,6,7,8-tetrahydrofolate	ChEBI
N-(5,10-Methylene-5,6,7,8-tetrahydropteroyl)-L-glutamate	ChEBI
(6R)-5,10-CH2-H4Folic acid	Generator
(6R)-5,10-Methylene-5,6,7,8-tetrahydrofolic acid	Generator
N-(5,10-Methylene-5,6,7,8-tetrahydropteroyl)-L-glutamic acid	Generator
(6R)-5,10-Methylenetetrahydrofolic acid(2-)	Generator

Molecular Formula

C₂₀H₂₁N₇O₆

Average Mass

455.432

Monoisotopic Mass

455.156428584

IUPAC Name

(4S)-4-({4-[(6aR)-3-imino-1-oxido-3H,4H,5H,6H,6aH,7H,8H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)-4-carboxybutanoate

Traditional Name

(4S)-4-({4-[(6aR)-3-imino-1-oxido-4H,5H,6H,6aH,7H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)-4-carboxybutanoate

CAS Registry Number

Not Available

SMILES

[H][C@@](CCC([O-])=O)(NC(=O)C1=CC=C(C=C1)N1CN2C3=C(NC[C@]2([H])C1)NC(=N)N=C3[O-])C(O)=O

InChI Identifier

InChI=1S/C20H23N7O6/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/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/p-2/t12-,13+/m1/s1

InChI Key

QYNUQALWYRSVHF-OLZOCXBDSA-L

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
N-acyl-alpha amino acid or derivatives
Hippuric acid
Hippuric acid or derivatives
Phenylimidazolidine
Alpha-amino acid or derivatives
Imidazopyrazine
Benzamide
Benzoic acid or derivatives
Benzoyl
Dialkylarylamine
Aniline or substituted anilines
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Pyrimidine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Imidazolidine
Amino acid or derivatives
Amino acid
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Secondary amine
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

5,10-methylenetetrahydrofolate(2-) (CHEBI:15636 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-2.6	ChemAxon
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	5.61	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	196.34 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	156.16 m³·mol⁻¹	ChemAxon
Polarizability	45.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

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)	2025-10-24	457.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	210.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	336.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	376.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	281.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	200.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1220.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	327.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	337.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	188.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	257.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	168.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	116.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	237.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	410.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	63.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	279.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1129.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	726.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_1	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])NC(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)[NH]4)N3C2)C=C1	standard non polar	2025-10-24	613.043
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_2	C[Si](C)(C)N(C(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)[NH]4)N3C2)C=C1)[C@@H](CCC(=O)[O-])C(=O)O	standard non polar	2025-10-24	2172.24
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic 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)CN2C2=C1[NH]C(=N)N=C2[O-]	standard non polar	2025-10-24	2194.68
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_4	C[Si](C)(C)N1C2=C(C([O-])=NC1=N)N1CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)[O-])C(=O)O)C=C3)C[C@H]1CN2	standard non polar	2025-10-24	1203.39
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_5	C[Si](C)(C)N=C1N=C([O-])C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)[O-])C(=O)O)C=C4)CN23)[NH]1	standard non polar	2025-10-24	2754.97
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_6	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])N(C(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)[NH]4)N3C2)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1940.84
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_7	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])NC(=O)C1=CC=C(N2C[C@H]3CN([Si](C)(C)C)C4=C(C([O-])=NC(=N)[NH]4)N3C2)C=C1	standard non polar	2025-10-24	2343.32
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_8	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])NC(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)N4[Si](C)(C)C)N3C2)C=C1	standard non polar	2025-10-24	1713.5
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_9	C[Si](C)(C)N=C1N=C([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)CN23)[NH]1	standard non polar	2025-10-24	1610.49
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_10	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)CN2C2=C1[NH]C(=N)N=C2[O-]	standard non polar	2025-10-24	2730.68
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_11	C[Si](C)(C)N(C(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)N4[Si](C)(C)C)N3C2)C=C1)[C@@H](CCC(=O)[O-])C(=O)O	standard non polar	2025-10-24	976.806
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_12	C[Si](C)(C)N=C1N=C([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)CN23)[NH]1	standard non polar	2025-10-24	2157.06
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_13	C[Si](C)(C)N=C1N=C([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)CN21	standard non polar	2025-10-24	1836.38
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic 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)C=C3)CN2C2=C1N([Si](C)(C)C)C(=N)N=C2[O-]	standard non polar	2025-10-24	1622.88
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_15	C[Si](C)(C)N=C1N=C([O-])C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)[O-])C(=O)O)C=C4)CN23)N1[Si](C)(C)C	standard non polar	2025-10-24	2988.81
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_16	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])N(C(=O)C1=CC=C(N2C[C@H]3CN([Si](C)(C)C)C4=C(C([O-])=NC(=N)[NH]4)N3C2)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1695.93
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_17	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])N(C(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)N4[Si](C)(C)C)N3C2)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1556.07
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_18	C[Si](C)(C)N=C1N=C([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)[Si](C)(C)C)C=C4)CN23)[NH]1	standard non polar	2025-10-24	848.591
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_19	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])NC(=O)C1=CC=C(N2C[C@H]3CN([Si](C)(C)C)C4=C(C([O-])=NC(=N)N4[Si](C)(C)C)N3C2)C=C1	standard non polar	2025-10-24	1601.75
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_20	C[Si](C)(C)N=C1N=C([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)CN21	standard non polar	2025-10-24	1689.47
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_21	C[Si](C)(C)N=C1N=C([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)CN23)N1[Si](C)(C)C	standard non polar	2025-10-24	1543.74
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_22	C[Si](C)(C)N=C1N=C([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)CN21	standard non polar	2025-10-24	3641.21
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_23	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)CN2C2=C1N([Si](C)(C)C)C(=N)N=C2[O-]	standard non polar	2025-10-24	1879.48
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_24	C[Si](C)(C)N=C1N=C([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)CN23)N1[Si](C)(C)C	standard non polar	2025-10-24	1197.67
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_25	C[Si](C)(C)N=C1N=C([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)CN23)N1[Si](C)(C)C	standard non polar	2025-10-24	2380.98
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_26	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])N(C(=O)C1=CC=C(N2C[C@H]3CN([Si](C)(C)C)C4=C(C([O-])=NC(=N)N4[Si](C)(C)C)N3C2)C=C1)[Si](C)(C)C	standard non polar	2025-10-24	1922.91
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_27	C[Si](C)(C)N=C1N=C([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)[Si](C)(C)C)C=C3)CN21	standard non polar	2025-10-24	1929.44
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_28	C[Si](C)(C)N=C1N=C([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)[Si](C)(C)C)C=C4)CN23)N1[Si](C)(C)C	standard non polar	2025-10-24	1301.87
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_29	C[Si](C)(C)N=C1N=C([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)CN23)N1[Si](C)(C)C	standard non polar	2025-10-24	2807.1
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_30	C[Si](C)(C)N=C1N=C([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)CN23)N1[Si](C)(C)C	standard non polar	2025-10-24	1151.1
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_31	C[Si](C)(C)N=C1N=C([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)[Si](C)(C)C)C=C4)CN23)N1[Si](C)(C)C	standard non polar	2025-10-24	1133.7
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_1	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])NC(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)[NH]4)N3C2)C=C1	standard polar	2025-10-24	2144.54
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_2	C[Si](C)(C)N(C(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)[NH]4)N3C2)C=C1)[C@@H](CCC(=O)[O-])C(=O)O	standard polar	2025-10-24	2222.06
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic 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)CN2C2=C1[NH]C(=N)N=C2[O-]	standard polar	2025-10-24	3028.86
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_4	C[Si](C)(C)N1C2=C(C([O-])=NC1=N)N1CN(C3=CC=C(C(=O)N[C@@H](CCC(=O)[O-])C(=O)O)C=C3)C[C@H]1CN2	standard polar	2025-10-24	3257.3
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_5	C[Si](C)(C)N=C1N=C([O-])C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)[O-])C(=O)O)C=C4)CN23)[NH]1	standard polar	2025-10-24	1884.04
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_6	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])N(C(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)[NH]4)N3C2)C=C1)[Si](C)(C)C	standard polar	2025-10-24	2344.39
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_7	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])NC(=O)C1=CC=C(N2C[C@H]3CN([Si](C)(C)C)C4=C(C([O-])=NC(=N)[NH]4)N3C2)C=C1	standard polar	2025-10-24	1422.41
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_8	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])NC(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)N4[Si](C)(C)C)N3C2)C=C1	standard polar	2025-10-24	2522.26
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_9	C[Si](C)(C)N=C1N=C([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)CN23)[NH]1	standard polar	2025-10-24	2353.3
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_10	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)CN2C2=C1[NH]C(=N)N=C2[O-]	standard polar	2025-10-24	2145.39
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_11	C[Si](C)(C)N(C(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)N4[Si](C)(C)C)N3C2)C=C1)[C@@H](CCC(=O)[O-])C(=O)O	standard polar	2025-10-24	2566.75
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_12	C[Si](C)(C)N=C1N=C([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)CN23)[NH]1	standard polar	2025-10-24	2893.27
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_13	C[Si](C)(C)N=C1N=C([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)CN21	standard polar	2025-10-24	2983.9
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic 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)C=C3)CN2C2=C1N([Si](C)(C)C)C(=N)N=C2[O-]	standard polar	2025-10-24	2335.72
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_15	C[Si](C)(C)N=C1N=C([O-])C2=C(NC[C@@H]3CN(C4=CC=C(C(=O)N[C@@H](CCC(=O)[O-])C(=O)O)C=C4)CN23)N1[Si](C)(C)C	standard polar	2025-10-24	1880.6
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_16	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])N(C(=O)C1=CC=C(N2C[C@H]3CN([Si](C)(C)C)C4=C(C([O-])=NC(=N)[NH]4)N3C2)C=C1)[Si](C)(C)C	standard polar	2025-10-24	1450.58
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_17	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])N(C(=O)C1=CC=C(N2C[C@H]3CNC4=C(C([O-])=NC(=N)N4[Si](C)(C)C)N3C2)C=C1)[Si](C)(C)C	standard polar	2025-10-24	2494.66
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_18	C[Si](C)(C)N=C1N=C([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)[Si](C)(C)C)C=C4)CN23)[NH]1	standard polar	2025-10-24	1967.04
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_19	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])NC(=O)C1=CC=C(N2C[C@H]3CN([Si](C)(C)C)C4=C(C([O-])=NC(=N)N4[Si](C)(C)C)N3C2)C=C1	standard polar	2025-10-24	2517.41
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_20	C[Si](C)(C)N=C1N=C([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)CN21	standard polar	2025-10-24	1989.39
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_21	C[Si](C)(C)N=C1N=C([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)CN23)N1[Si](C)(C)C	standard polar	2025-10-24	955.655
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_22	C[Si](C)(C)N=C1N=C([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)CN21	standard polar	2025-10-24	1222.71
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_23	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)CN2C2=C1N([Si](C)(C)C)C(=N)N=C2[O-]	standard polar	2025-10-24	616.126
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_24	C[Si](C)(C)N=C1N=C([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)CN23)N1[Si](C)(C)C	standard polar	2025-10-24	3240.9
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_25	C[Si](C)(C)N=C1N=C([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)CN23)N1[Si](C)(C)C	standard polar	2025-10-24	2376.78
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_26	C[Si](C)(C)OC(=O)[C@H](CCC(=O)[O-])N(C(=O)C1=CC=C(N2C[C@H]3CN([Si](C)(C)C)C4=C(C([O-])=NC(=N)N4[Si](C)(C)C)N3C2)C=C1)[Si](C)(C)C	standard polar	2025-10-24	2677.13
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_27	C[Si](C)(C)N=C1N=C([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)[Si](C)(C)C)C=C3)CN21	standard polar	2025-10-24	2417.95
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_28	C[Si](C)(C)N=C1N=C([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)[Si](C)(C)C)C=C4)CN23)N1[Si](C)(C)C	standard polar	2025-10-24	1184.04
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_29	C[Si](C)(C)N=C1N=C([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)CN23)N1[Si](C)(C)C	standard polar	2025-10-24	2274.53
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_30	C[Si](C)(C)N=C1N=C([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)CN23)N1[Si](C)(C)C	standard polar	2025-10-24	2135.68
Gas Chromatography	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid_TMS_31	C[Si](C)(C)N=C1N=C([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)[Si](C)(C)C)C=C4)CN23)N1[Si](C)(C)C	standard polar	2025-10-24	1917.65

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

Not Available

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
MMDBr0024546	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid	(6S)-5,6,7,8-tetrahydrofolic acid	Methylenetetrahydrofolate--tRNA-(uracil-5-)-methyltransferase TrmFO	Methylation	RHEA	34755880
MMDBr0024548	(6S)-5,6,7,8-tetrahydrofolic acid	(6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid	Probable aminomethyltransferase	Methylation	RHEA	34755880

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
Viruses/Heunggongvirae	Uroviricota	9
Bacteria/Eubacteria	Cyanobacteria	35	Human
Bacteria/Eubacteria	Firmicutes	172	Human feces; Human ; Catfish ; Cattle ; Human supragingival plaque; Human subgingival plaque; Human saliva
Bacteria/Eubacteria	Proteobacteria	434	Human ; Human feces; River trout ; Cattle ; Rat ; Pig ; Lion ; Sheep ; Chicken ; Turkey ; Dog ; American dog tick ; Human subgingival plaque; Human saliva
Bacteria/Eubacteria	Actinobacteria	61	Human ; Cattle ; Human feces
Archaea/Archaea	Crenarchaeota	19
Bacteria/Eubacteria	Aquificae	5
Bacteria/Eubacteria	Bacteroidetes	14	Human ; Human feces
Archaea/Archaea	Thaumarchaeota	2
Bacteria/Eubacteria	Chloroflexi	10
Bacteria/Eubacteria	Chlorobi	11
Bacteria/Eubacteria	Deinococcus-thermus	5
Bacteria	Proteobacteria	8	Human ; Human feces; River trout ; Cattle ; Rat ; Pig ; Lion ; Sheep ; Chicken ; Turkey ; Dog ; American dog tick ; Human subgingival plaque; Human saliva
Eukaryota/Fungi	Ascomycota	10	Human feces; Human saliva; Human supragingival plaque
Bacteria/Eubacteria	Elusimicrobia	2
Archaea/Archaea	Euryarchaeota	23
Bacteria/Eubacteria	Acidobacteria	3
Bacteria/Eubacteria	Thermotogae	10
Bacteria/Eubacteria	Spirochaetes	18	Human ; Pig ; Relapsing fever tick
Bacteria/Eubacteria	Planctomycetes	1
Archaea	Crenarchaeota	1
Bacteria	nah	1
Viruses/Bamfordvirae	Nucleocytoviricota	3
Eukaryota/Fungi	Microsporidia	1
Bacteria/Eubacteria	Tenericutes	19	Human ; Goat ; Pig
Eukaryota/Fungi	Basidiomycota	3	Human feces
Viruses/Heunggongvirae	Peploviricota	6
Bacteria/Eubacteria	Fusobacteria	1	Human ; Human feces
Archaea	Euryarchaeota	1
Bacteria	Tenericutes	2	Human ; Goat ; Pig
Bacteria/Eubacteria	Verrucomicrobia	2	Human ; Human feces
Bacteria/Eubacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria/Eubacteria	Dictyoglomi	2
Bacteria/Eubacteria	Nitrospirae	1
Bacteria	Actinobacteria	1	Human ; Cattle ; Human feces

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

7827491

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9548565

PDB ID

Not Available

ChEBI ID

15636

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (6R)-5,10-methylene-5,6,7,8-tetrahydrofolic acid (MMDBc0054976)

MOL for #<Metabolite:0x00007f2e3bd56fb8>

3D MOL for #<Metabolite:0x00007f2e3bd56fb8>

3D SDF for #<Metabolite:0x00007f2e3bd56fb8>

3D-SDF for #<Metabolite:0x00007f2e3bd56fb8>

PDB for #<Metabolite:0x00007f2e3bd56fb8>

3D PDB for #<Metabolite:0x00007f2e3bd56fb8>

SMILES for #<Metabolite:0x00007f2e3bd56fb8>

INCHI for #<Metabolite:0x00007f2e3bd56fb8>

Structure for #<Metabolite:0x00007f2e3bd56fb8>

3D Structure for #<Metabolite:0x00007f2e3bd56fb8>