CHEBI:15638 - (6R)-5,10-methenyltetrahydrofolic acid

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ChEBI Name (6R)-5,10-methenyltetrahydrofolic acid
ChEBI ID CHEBI:15638
ChEBI ASCII Name (6R)-5,10-methenyltetrahydrofolic acid
Definition The 5,10-methenyl derivative of tetrahydrofolic acid arising from enzymatic cyclisation of 5-formyltetrahydrofolic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:12069, CHEBI:12068, CHEBI:1987
Supplier Information
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Formula C20H22N7O6
Net Charge +1
Average Mass 456.43226
Monoisotopic Mass 456.163
InChI InChI=1S/C20H21N7O6/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/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/p+1/t12-,13+/m1/s1
InChIKey MEANFMOQMXYMCT-OLZOCXBDSA-O
SMILES [H][C@]12CNc3nc(N)[nH]c(=O)c3[N+]1=CN(C2)c1ccc(cc1)C(=O)N[C@@H](CCC(O)=O)C(O)=O
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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) has functional parent (6R)-5,10-methylenetetrahydrofolic acid (CHEBI:1989)
(6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) has role Escherichia coli metabolite (CHEBI:76971)
(6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) has role mouse metabolite (CHEBI:75771)
(6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) is a methylenetetrahydrofolic acid (CHEBI:25297)
(6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) is conjugate acid of (6R)-5,10-methenyltetrahydrofolate (CHEBI:57455)
Incoming (6R)-5,10-methenyltetrahydrofolate (CHEBI:57455) is conjugate base of (6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638)
IUPAC Name
N-{4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydro-8H-imidazo[1,5-f]pteridin-10-ium-8-yl]benzoyl}-L-glutamic acid
Synonyms Sources
(6R)-5,10-CH+-H4folate JCBN
5,10-Methenyltetrahydrofolate KEGG COMPOUND
5,10-methenyltetrahydropteroylglutamate ChemIDplus
Anhydroleucovorin ChemIDplus
Manual Xrefs Databases
C00019687 KNApSAcK
C00445 KEGG COMPOUND
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Registry Numbers Types Sources
6184059 Beilstein Registry Number Beilstein
7444-29-3 CAS Registry Number ChemIDplus
Last Modified
27 January 2016
General Comment
2004-01-09 The naturally occurring compound is the tetrahydrofolate 6R stereoisomer.