Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0742)
Drug Name
Folic acid
Synonyms
Folacid; Folacin; Folaemin [Netherlands]; Folasic (Australia); Folate; Folbal; Folcidin; Folcysteine; Foldine; Foldine [France]; Folettes; Foliamin; Folicet; Folico (Italy); Folina (Italy); Folipac; Folsan; Folsaure; Folsav; Folvite; Acifolic; Antianemia factor; Acfol (Spain); Cytofol; Factor U; Incafolic; Millafol; Mittafol; PteGlu; Pteroyl-L-glutamic acid; Pteroyl-L-monoglutamic acid; Pteroylglutamic acid; Pteroylmonoglutamate; Pteroylmonoglutamic acid; Vitamin B9; Vitamin Bc; Vitamin Be; Vitamin M; folic acid; 59-30-3; Facid; Folan
Indication Vitamin deficiency [ICD11: 5B55] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 441.4 Topological Polar Surface Area 209
Heavy Atom Count 32 Rotatable Bond Count 9
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
135398658
PubChem SID
3787 ; 584223 ; 829573 ; 831381 ; 831592 ; 831633 ; 831664 ; 834516 ; 835597 ; 835744 ; 837196 ; 841329 ; 7847138 ; 7887399 ; 7887539 ; 7979297 ; 8144505 ; 8149795 ; 8153763 ; 10318222 ; 10321330 ; 11112150 ; 11335669 ; 11360908 ; 11364275 ; 11366837 ; 11369399 ; 11371658 ; 11375360 ; 11377561 ; 11461880 ; 11485093 ; 11489275 ; 11490565 ; 11493565 ; 11495195 ; 11537760 ; 14857129 ; 14930521 ; 16028504 ; 16077361 ; 22389272 ; 24845192 ; 24894950 ; 24894973 ; 24894977 ; 24894979 ; 26612259 ; 26680757 ; 26704619
ChEBI ID
CHEBI:15641
CAS Number
59-30-3
TTD Drug ID
D0Z0DW
Formula
C19H19N7O6
Canonical SMILES
C1=CC(=CC=C1C(=O)NC(CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)NC(=N3)N
InChI
1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1
InChIKey
OVBPIULPVIDEAO-LBPRGKRZSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
7,8-dihydrofolate (H2folate) DM000334
135398604
Reduction - Reduction 1 [2]
Tetrahydrofolic acid DM002049
135444742
Reduction - Reduction 1 [2]
5,10-methylene tetrahydrofolate (THF) DM002050
135398652
Unclear 2 [2]
5-Methyltetrahydrofolate DM002051
135483998
Unclear 3 [2]
Methionine DM003070
6992087
Unclear 4 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001083 Folic acid Dihydrofolate Reduction - Reduction DHFR [2]
MR001084 Folic acid Tetrahydrofolic acid Reduction - Reduction DHFR [2]
MR001080 Tetrahydrofolic acid 5,10-methylene tetrahydrofolate (THF) Unclear MTHFD2 [2]
MR001081 5,10-methylene tetrahydrofolate (THF) 5-Methyltetrahydrofolate Unclear MTHFR [2]
MR001082 5-Methyltetrahydrofolate Methionine Unclear MTR [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial (MTHFD2) DMEN085 Homo sapiens
MTDC_HUMAN
2.1.2.10
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Dihydrofolate reductase (DHFR) DME0141 Homo sapiens
DYR_HUMAN
1.5.1.3
[4]
Dihydrofolate reductase (folA) DME1049 Escherichia coli
DYR_ECOLI
1.5.1.3
[5] , [6]
Dihydrofolate reductase (folA) DME1050 Lactobacillus casei
DYR_LACCA
1.5.1.3
[7]
Dihydrofolate reductase (folA) DME1051 Chlamydia muridarum
Q9PJC7_CHLMU
1.5.1.3
[8] , [9]
Folylpolyglutamate synthetase (fpgS) DME1239 Lactobacillus casei
FPGS_LACCA
6.3.2.17
[10]
Gamma-Glu-X carboxypeptidase (GGH) DME0142 Homo sapiens
GGH_HUMAN
3.4.19.9
[11]
Methionine synthase reductase (MTRR) DME0431 Homo sapiens
MTRR_HUMAN
1.16.1.8
[12]
Methylenetetrahydrofolate reductase (MTHFR) DME0083 Homo sapiens
MTHR_HUMAN
1.5.1.20
[13]
RNA cytidine acetyltransferase (hALP) DME0007 Homo sapiens
NAT10_HUMAN
2.3.1.5
[14]
Vitamin B12 methionine synthase (MTR) DME0153 Homo sapiens
METH_HUMAN
2.1.1.13
[15]
⏷ Show the Full List of 12  DME(s)
References
1 Folic Acid was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 DrugBank(Pharmacology-Metabolism)Folic acid
3 Chronic ethanol feeding and folate deficiency activate hepatic endoplasmic reticulum stress pathway in micropigs. Am J Physiol Gastrointest Liver Physiol. 2005 Jul;289(1):G54-63.
4 The dihydrofolate reductase 19 bp polymorphism is not associated with biomarkers of folate status in healthy young adults, irrespective of folic acid intake. J Nutr. 2015 Oct;145(10):2207-11.
5 Measurement of the uptake of radioactive para-aminobenzoic acid monitors folate biosynthesis in Escherichia coli K-12. Anal Biochem. 1994 Feb 1;216(2):427-30.
6 The influence of CsgD on the expression of genes of folate metabolism and hmp in Escherichia coli K-12. Arch Microbiol. 2013 Aug;195(8):559-69.
7 Molecular cloning of the gene for dihydrofolate reductase from Lactobacillus casei. Gene. 1982 Feb;17(2):229-33.
8 Biophysical principles predict fitness landscapes of drug resistance. Proc Natl Acad Sci U S A. 2016 Mar 15;113(11):E1470-8.
9 The Genital tract virulence factor pGP3 is essential for Chlamydia muridarum colonization in the gastrointestinal tract. Infect Immun. 2017 Dec 19;86(1). pii: e00429-17.
10 Mutagenesis of folylpolyglutamate synthetase indicates that dihydropteroate and tetrahydrofolate bind to the same site. Biochemistry. 2008 Feb 26;47(8):2388-96.
11 Optimization of the trienzyme extraction for the microbiological assay of folate in vegetables. J Agric Food Chem. 2007 May 16;55(10):3884-8.
12 Polymorphisms in genes involved in folate metabolism as maternal risk factors for Down syndrome in China. J Zhejiang Univ Sci B. 2008 Feb;9(2):93-9.
13 Genetic variation: impact on folate (and choline) bioefficacy. Int J Vitam Nutr Res. 2010 Oct;80(4-5):319-29.
14 Arylamine N-acetyltransferase in human red blood cells. Biochem Pharmacol. 1992 Sep 25;44(6):1099-104.
15 Metabolic derangement of methionine and folate metabolism in mice deficient in methionine synthase reductase. Mol Genet Metab. 2007 May;91(1):85-97.

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