MiMeDB: Showing metabocard for 10-Formyltetrahydrofolic acid (MMDBc0033012)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:31:05 UTC

Update Date

2023-12-14 16:53:07 UTC

Metabolite ID

MMDBc0033012

Metabolite Identification

Common Name

10-Formyltetrahydrofolic acid

Description

10-Formyltetrahydrofolate (10-CHO-THF) is form of tetrahydrofolate that acts as a donor of formyl groups in anabolism. In particular, 10-CHO-THF is used as a substrate in a number of formyltransferase reactions. It plays an important role in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase, as well as in the formylation of the methionyl initiator tRNA (fMet-tRNA), when 10-CHO-THF is a substrate for methionyl-tRNA formyltransferase. 10-Formyltetrahydrofolate is a substrate for Trifunctional purine biosynthetic protein adenosine-3, Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), 10-formyltetrahydrofolate dehydrogenase, Folylpolyglutamate synthase (mitochondrial), Bifunctional purine biosynthesis protein PURH and C-1-tetrahydrofolate synthase (cytoplasmic).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222232D          

 34 36  0  0  1  0            999 V2000
   -0.7145   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.6502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.0627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5736    2.0627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    0.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    4.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 30  1  2  0  0  0  0
 30  6  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  3 28  1  0  0  0  0
  4  8  1  0  0  0  0
  7  5  1  0  0  0  0
 28  6  1  0  0  0  0
  8  9  1  1  0  0  0
  9 32  1  0  0  0  0
 32 10  1  0  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 16 17  2  0  0  0  0
 20 18  1  1  0  0  0
 26 19  2  0  0  0  0
 20 24  1  0  0  0  0
 20 22  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7  8  1  0  0  0  0
 28 29  2  0  0  0  0
 30 31  1  0  0  0  0
 32 34  1  0  0  0  0
 34 33  2  0  0  0  0
M  END


  Mrv0541 02241222232D          

 34 36  0  0  1  0            999 V2000
   -0.7145   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.6502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.0627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5736    2.0627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    0.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    4.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 30  1  2  0  0  0  0
 30  6  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  3 28  1  0  0  0  0
  4  8  1  0  0  0  0
  7  5  1  0  0  0  0
 28  6  1  0  0  0  0
  8  9  1  1  0  0  0
  9 32  1  0  0  0  0
 32 10  1  0  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 16 17  2  0  0  0  0
 20 18  1  1  0  0  0
 26 19  2  0  0  0  0
 20 24  1  0  0  0  0
 20 22  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7  8  1  0  0  0  0
 28 29  2  0  0  0  0
 30 31  1  0  0  0  0
 32 34  1  0  0  0  0
 34 33  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033012

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC2=C(N[C@@H](CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11-,13+/m1/s1

> <INCHI_KEY>
AUFGTPPARQZWDO-YPMHNXCESA-N

> <FORMULA>
C20H23N7O7

> <MOLECULAR_WEIGHT>
473.4393

> <EXACT_MASS>
473.165896125

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
46.63277487497841

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[4-(N-{[(6R)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid

> <ALOGPS_LOGP>
-1.79

> <JCHEM_LOGP>
-3.371732827151703

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.597415477616566

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8185105858286112

> <JCHEM_PKA_STRONGEST_BASIC>
4.472180456626537

> <JCHEM_POLAR_SURFACE_AREA>
215.55

> <JCHEM_REFRACTIVITY>
124.88119999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-formyltetrahydrofolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.334  -1.540   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334   1.540   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       1.334  -1.540   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      -2.667   0.770   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669   5.390   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      12.003   3.080   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      13.337   8.470   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.337   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.004   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.670   3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.670   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.337   5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.671   6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.671   7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.004   8.470   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334   3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -4.001  -1.540   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       5.335   0.770   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0       4.001  -1.540   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.335  -0.770   0.000  0.00  0.00           C+0
CONECT    1   30    2                                                       
CONECT    2    1    3    5                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    8                                                       
CONECT    5    2    7                                                       
CONECT    6   30   28                                                       
CONECT    7    5    8                                                       
CONECT    8    4    9    7                                                  
CONECT    9    8   32                                                       
CONECT   10   32   12   13                                                  
CONECT   11   12   15                                                       
CONECT   12   10   11                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   11   14   16                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   20                                                       
CONECT   19   26                                                            
CONECT   20   18   24   22                                                  
CONECT   21   22                                                            
CONECT   22   20   21   23                                                  
CONECT   23   22                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   19   25   27                                                  
CONECT   27   26                                                            
CONECT   28    3    6   29                                                  
CONECT   29   28                                                            
CONECT   30    1    6   31                                                  
CONECT   31   30                                                            
CONECT   32    9   10   34                                                  
CONECT   33   34                                                            
CONECT   34   32   33                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

Synonyms

Value	Source
(6S)-10-HCO-H4Folate	ChEBI
10-Formyl-THF	ChEBI
10-Formyltetrahydrofolate	ChEBI
10-Formyltetrahydropteroylglutamic acid	ChEBI
10-FTHF	ChEBI
N-(10-Formyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid	ChEBI
(6S)-10-HCO-H4Folic acid	Generator
10-Formyltetrahydrofolic acid	Generator
10-Formyltetrahydropteroylglutamate	Generator
N-(10-Formyl-5,6,7,8-tetrahydropteroyl)-L-glutamate	Generator

Molecular Formula

C₂₀H₂₃N₇O₇

Average Mass

473.4393

Monoisotopic Mass

473.165896125

IUPAC Name

(2S)-2-{[4-(N-{[(6R)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid

Traditional Name

10-formyltetrahydrofolic acid

CAS Registry Number

2800-34-2

SMILES

NC1=NC2=C(N[C@@H](CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1

InChI Identifier

InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11-,13+/m1/s1

InChI Key

AUFGTPPARQZWDO-YPMHNXCESA-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
Acylaminobenzoic acid or derivatives
Alpha-amino acid or derivatives
Anilide
Benzoic acid or derivatives
Benzamide
Benzoyl
Pyrimidone
Aminopyrimidine
Secondary aliphatic/aromatic amine
Dicarboxylic acid or derivatives
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous amide
Tertiary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid
Carboxylic acid derivative
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

formyltetrahydrofolic acid (CHEBI:15637 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-3.4	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.82	ChemAxon
pKa (Strongest Basic)	4.47	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	215.55 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	124.88 m³·mol⁻¹	ChemAxon
Polarizability	46.63 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_35) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a7i-0301900000-731bc9348489f24f80ff	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003r-0936800000-ade646bc1baf4b8851af	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001r-0910000000-a7975e3a08f3a92a4ce2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-53fa6981f67bce467289	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uml-1122900000-95a426dd0ca2a0207dbb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9741000000-dbaf84d2dcb0c0d71757	2015-09-15	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Lysosome
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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001233	10-Formyltetrahydrofolic acid	10-Formyltetrahydrofolate-[Glu](5)	folylpolyglutamate synthase	VMH	10777604
MMDBr0001242	10-Formyltetrahydrofolic acid	Tetrahydrofolic acid	aldehyde dehydrogenase 1 family, member L1	VMH; KEGG	2733692
MMDBr0001243	Formic acid	10-Formyltetrahydrofolic acid	methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 1, methenyltetrahydrofolate cyclohydrolase, formyltetrahydrofolate synthetase	VMH	12937168
MMDBr0001270	10-Formyltetrahydrofolic acid	5'-Phosphoribosyl-N-formylglycineamide	phosphoribosylglycinamide formyltransferase, phosphoribosylglycinamide synthetase, phosphoribosylaminoimidazole synthetase	VMH; KEGG	12450384 2183217 9328467 9473452
MMDBr0001282	10-Formyltetrahydrofolate-[Glu](5)	10-Formyltetrahydrofolic acid	gamma-glutamyl hydrolase (conjugase, folylpolygammaglutamyl hydrolase)	VMH	11375437 2867095 9614206
MMDBr0001283	10-Formyltetrahydrofolate-[Glu](5)	10-Formyltetrahydrofolic acid	gamma-glutamyl hydrolase (conjugase, folylpolygammaglutamyl hydrolase)	VMH	11375437 2867095 9614206
MMDBr0001690	5,10-Methenyltetrahydrofolic acid	10-Formyltetrahydrofolic acid	methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 1-like	VMH; KEGG	30371894
MMDBr0006939	10-Formyltetrahydrofolic acid	5'-Phosphoribosyl-N-formylglycineamide	Not Available	VMH	30371894
MMDBr0007191	10-Formyltetrahydrofolic acid	Formic acid	Not Available	VMH	30371894
MMDBr0007405	10-Formyltetrahydrofolic acid	10-Formyltetrahydrofolate-[Glu](5)	Not Available	VMH	30371894
MMDBr0007492	5,10-Methenyltetrahydrofolic acid	10-Formyltetrahydrofolic acid	Not Available	VMH; KEGG	30371894
MMDBr0007706	10-Formyltetrahydrofolic acid	Phosphoribosyl formamidocarboxamide	Not Available	VMH; KEGG	30371894
MMDBr0008072	Formic acid	10-Formyltetrahydrofolic acid	Not Available	VMH	30371894

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria	Firmicutes	369	Human feces; Human pleural fluid plaque; Pig ; Human ; Human stool; Human subgingival plaque; Cattle ; Human saliva	Metabolic reconstruction
Bacteria	Proteobacteria	173	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	119	Human feces; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Human pleural fluid plaque; Human dental plaque; Human sputum; Human nasopharyngeal swab	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	116	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00007251

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

6326742

PDB ID

Not Available

ChEBI ID

15637

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Johlin FC, Swain E, Smith C, Tephly TR: Studies on the mechanism of methanol poisoning: purification and comparison of rat and human liver 10-formyltetrahydrofolate dehydrogenase. Mol Pharmacol. 1989 Jun;35(6):745-50. [PubMed:2733692 ]
Kirksey TJ, Appling DR: Site-directed mutagenesis of a highly conserved aspartate in the putative 10-formyl-tetrahydrofolate binding site of yeast C1-tetrahydrofolate synthase. Arch Biochem Biophys. 1996 Sep 1;333(1):251-9. doi: 10.1006/abbi.1996.0388. [PubMed:8806778 ]
Baggott JE, Tamura T: Bioactivity of orally administered unnatural isomers, [6R]-5-formyltetrahydrofolate and [6S]-5,10-methenyltetrahydrofolate, in humans. Biochim Biophys Acta. 1999 Oct 18;1472(1-2):323-32. doi: 10.1016/s0304-4165(99)00135-x. [PubMed:10572954 ]
Boger DL, Labroli MA, Marsilje TH, Jin Q, Hedrick MP, Baker SJ, Shim JH, Benkovic SJ: Conformationally restricted analogues designed for selective inhibition of GAR Tfase versus thymidylate synthase or dihydrofolate reductase. Bioorg Med Chem. 2000 May;8(5):1075-86. doi: 10.1016/s0968-0896(00)00051-1. [PubMed:10882019 ]
Baggott JE, Robinson CB, Johnston KE: Bioactivity of [6R]-5-formyltetrahydrofolate, an unusual isomer, in humans and Enterococcus hirae, and cytochrome c oxidation of 10-formytetrahydrofolate to 10-formyldihydrofolate. Biochem J. 2001 Feb 15;354(Pt 1):115-22. doi: 10.1042/0264-6021:3540115. [PubMed:11171086 ]
Xu L, Li C, Olson AJ, Wilson IA: Crystal structure of avian aminoimidazole-4-carboxamide ribonucleotide transformylase in complex with a novel non-folate inhibitor identified by virtual ligand screening. J Biol Chem. 2004 Nov 26;279(48):50555-65. doi: 10.1074/jbc.M406801200. Epub 2004 Sep 7. [PubMed:15355974 ]

Showing metabocard for 10-Formyltetrahydrofolic acid (MMDBc0033012)

MOL for #<Metabolite:0x00007fed0401a6a0>

3D MOL for #<Metabolite:0x00007fed0401a6a0>

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3D PDB for #<Metabolite:0x00007fed0401a6a0>

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Structure for #<Metabolite:0x00007fed0401a6a0>

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