CHEBI:1989 - (6R)-5,10-methylenetetrahydrofolic acid

ChEBI IDCHEBI:1989
ChEBI Name(6R)-5,10-methylenetetrahydrofolic acid
Stars
ASCII Name(6R)-5,10-methylenetetrahydrofolic acid
DefinitionThe (6R)-stereoisomer of 5,10-methylenetetrahydrofolic acid.
Last Modified25 July 2019
DownloadsMolfile
FormulaC20H23N7O6
Net Charge0
Average Mass457.447
Monoisotopic Mass457.17098
SMILES[H][C@]12CNc3nc(N)nc(=O)c3N1CN(c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)C2
InChIInChI=1S/C20H23N7O6/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/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13+/m1/s1
InChIKeyQYNUQALWYRSVHF-OLZOCXBDSA-N
Species of MetaboliteComponentSourceComments
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Biological Roles:
cofactor  An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
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.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
(6R)-5,10-methylenetetrahydrofolic acid (CHEBI:1989) has role Escherichia coli metabolite (CHEBI:76971)
(6R)-5,10-methylenetetrahydrofolic acid (CHEBI:1989) has role cofactor (CHEBI:23357)
(6R)-5,10-methylenetetrahydrofolic acid (CHEBI:1989) has role mouse metabolite (CHEBI:75771)
(6R)-5,10-methylenetetrahydrofolic acid (CHEBI:1989) is a 5,10-methylenetetrahydrofolic acid (CHEBI:20502)
(6R)-5,10-methylenetetrahydrofolic acid (CHEBI:1989) is conjugate acid of (6R)-5,10-methylenetetrahydrofolate(2−) (CHEBI:15636)
Incoming Relation(s)
(6R)-5,10-methenyltetrahydrofolic acid (CHEBI:15638) has functional parent (6R)-5,10-methylenetetrahydrofolic acid (CHEBI:1989)
5,10-methylenetetrahydrofolate heptaglutamate (CHEBI:60976) has functional parent (6R)-5,10-methylenetetrahydrofolic acid (CHEBI:1989)
(6R)-5,10-methylenetetrahydrofolate(2−) (CHEBI:15636) is conjugate base of (6R)-5,10-methylenetetrahydrofolic acid (CHEBI:1989)
IUPAC Name 
N-{4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl]benzoyl}-L-glutamic acid
Synonyms  Source
5,10-MethylenetetrahydrofolateKEGG COMPOUND
(6R)-5,10-MethylenetetrahydrofolateKEGG COMPOUND
5,10-Methylene-THFKEGG COMPOUND
5,10-methylenetetrahydrofolic acidChemIDplus
Manual XrefsDatabases
C00143KEGG COMPOUND
C00007250KNApSAcK
Registry NumbersSources
Reaxys:5467239Reaxys
CAS:3432-99-3KEGG COMPOUND
CAS:3432-99-3ChemIDplus