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 473.16590
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:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) 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).
water-soluble vitamin (role)
Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine.
(via B vitamin )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
(via B vitamin )
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
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
Manual Xrefs 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
23 December 2018
General Comment
2004-01-09 The naturally occurring compound is the 6S stereoisomer.