Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:02:46 UTC
Update Date2022-08-31 17:43:31 UTC
Metabolite IDMMDBc0030309
Metabolite Identification
Common Name5,10-Methenyltetrahydrofolate
Description5,10-Methenyltetrahydrofolate (5,10-CH=THF) is a form of tetrahydrofolate that is an intermediate in metabolism. 5,10-CH=THF is a coenzyme that accepts and donates methenyl (CH=) groups.;Methylene tetrahydrofolate (CH2FH4) is formed from tetrahydrofolate by the addition of methylene groups from one of three carbon donors: formaldehyde, serine, or glycine. Methyl tetrahydrofolate(CH3FH4) can be made from methylene tetrahydrofolate by reduction of the methylene group, and formyl tetrahydrofolate (CHOFH4, folinic acid) is made by oxidation of methylene tetrahydrofolate.; In the form of a series of tetrahydrofolate compounds, folate derivatives are substrates in a number of single-carbon-transfer reactions, and also are involved in the synthesis of dTMP (2'-deoxythymidine-5'-phosphate) from dUMP (2'-deoxyuridine-5'-phosphate).
Structure
Synonyms
ValueSource
(6R)-5,10-CH(+)-H4FolateChEBI
5,10-MethenyltetrahydropteroylglutamateChEBI
AnhydroleucovorinChEBI
(6R)-5,10-CH(+)-H4Folic acidGenerator
5,10-Methenyltetrahydropteroylglutamic acidGenerator
5,10-Methenyltetrahydrofolic acidGenerator
5,10-MethenyltetrahydrofolateChEBI
(6R)-5,10-MethenyltetrahydrofolateGenerator
Molecular FormulaC20H22N7O6
Average Mass456.432
Monoisotopic Mass456.163156471
IUPAC Name(6aR)-3-amino-8-(4-{[(1S)-1,3-dicarboxypropyl]carbamoyl}phenyl)-1-oxo-1H,2H,5H,6H,6aH,7H,8H-10λ⁵-imidazo[1,5-f]pteridin-10-ylium
Traditional Nameanhydroleucovorin
CAS Registry Number7444-29-3
SMILES
[H][C@@]12CN(C=[N+]1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O
InChI Identifier
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
InChI KeyMEANFMOQMXYMCT-OLZOCXBDSA-O