5,10-Methenyltetrahydrofolate

5,10-Methenyltetrahydrofolate

IUPAC name N-[4-(3-amino-1-oxo-1,4,5,6,6a,7-hexahydro-8H-imidazo[1,5-f]pteridin-10-ium-8-yl)benzoyl]-L-glutamic acid
Other names 5,10-CH=THF
Identifiers
CAS number	7444-29-3
PubChem	644350
ChemSpider	133^Y
MeSH	5,10-methenyltetrahydrofolate
ChEMBL	CHEMBL46521^Y
Jmol-3D images	Image 1
SMILES O=C(O)C(NC(=O)c1ccc(cc1)N4/C=[N+]3/C2=C(/N\C(=N/C2=O)N)NCC3C4)CCC(=O)O
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^Y Key: MEANFMOQMXYMCT-UHFFFAOYSA-O^Y InChI=1/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 Key: MEANFMOQMXYMCT-IKLDFBCSAN
Properties
Molecular formula	C₂₀H₂₁₃N₇O₆
Molar mass	455.42 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

5,10-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.

It is produced from 5,10-methylenetetrahydrofolate by either a NAD+ dependent methylenetetrahydrofolate dehydrogenase, or a NADP+ dependent dehydrogense.^[1] It can also be produced as an intermediate in histidine catabolism, by formiminotransferase cyclodeaminase, from 5-formiminotetrahydrofolate.

5,10-CH=THF is a substrate for methenyltetrahydrofolate cyclohydrolase, which converts it into 10-formyltetrahydrofolate.

References

^ Fowler B (February 2001). "The folate cycle and disease in humans". Kidney Int. Suppl. 78: S221–9. doi:10.1046/j.1523-1755.2001.07851.x. PMID 11169015.