CHEBI:15640 - 5-formyltetrahydrofolic acid

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ChEBI Name 5-formyltetrahydrofolic acid
ChEBI ID CHEBI:15640
Definition A formyltetrahydrofolic acid in which the formyl group is located at position 5.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2057, CHEBI:12127, CHEBI:18607
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Formula C20H23N7O7
Net Charge 0
Average Mass 473.43930
Monoisotopic Mass 473.166
InChI InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12?,13-/m0/s1
InChIKey VVIAGPKUTFNRDU-ABLWVSNPSA-N
SMILES [H]C(=O)N1C(CNc2ccc(cc2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNc2nc(N)[nH]c(=O)c12
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 5-formyltetrahydrofolic acid (CHEBI:15640) has role Escherichia coli metabolite (CHEBI:76971)
5-formyltetrahydrofolic acid (CHEBI:15640) has role mouse metabolite (CHEBI:75771)
5-formyltetrahydrofolic acid (CHEBI:15640) is a formyltetrahydrofolic acid (CHEBI:24099)
5-formyltetrahydrofolic acid (CHEBI:15640) is conjugate acid of 5-formyltetrahydrofolate(2−) (CHEBI:65340)
Incoming (6S)-5-formyltetrahydrofolic acid (CHEBI:63606) is a 5-formyltetrahydrofolic acid (CHEBI:15640)
5-formyltetrahydrofolate(2−) (CHEBI:65340) is conjugate base of 5-formyltetrahydrofolic acid (CHEBI:15640)
IUPAC Name
N-[4-({[2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid
Synonyms Sources
(5-formyl-5,6,7,8-tetrahydropteroyl)glutamate ChEBI
10-Formyl-7,8-dihydrofolic acid ChemIDplus
5-Formyl-5,6,7,8-tetrahydrofolic acid ChemIDplus
5-Formyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid ChemIDplus
5-Formyltetrahydrofolate KEGG COMPOUND
5-formyltetrahydrofolic acid UniProt
Acide folinique ChemIDplus
folinate ChEBI
Folinic acid KEGG COMPOUND
L(-)-5-Formyl-5,6,7,8-tetrahydrofolic acid KEGG COMPOUND
Leucovorin KEGG COMPOUND
Leucovorinum ChemIDplus
N-(5-formyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid ChEBI
N5-Formyl-5,6,7,8-tetrahydrofolic acid ChemIDplus
N5-Formyltetrahydrofolic acid ChemIDplus
Database Links Databases
1232 DrugCentral
C03479 KEGG COMPOUND
D07986 KEGG DRUG
DB03256 DrugBank
Folinic_acid Wikipedia
LSM-5146 LINCS
View more database links
Registry Numbers Types Sources
101688 Reaxys Registry Number Reaxys
58-05-9 CAS Registry Number KEGG COMPOUND
58-05-9 CAS Registry Number ChemIDplus
Last Modified
22 February 2017
General Comment
2004-01-09 The naturally occurring compound is the 6S stereoisomer.