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5,10-Methenyltetrahydrofolate

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5,10-Methenyltetrahydrofolate
Skeletal formula of 5,10-methenyltetrahydrofolate
Space-filling model of the 5,10-methenyltetrahydrofolate cation
Names
IUPAC name N-pteridin-10-ium-8-yl)benzoyl]-L-glutamic acid
Other names 5,10-CH=THF
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
MeSH 5,10-methenyltetrahydrofolate
PubChem CID
CompTox Dashboard (EPA)
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+1Key: MEANFMOQMXYMCT-UHFFFAOYSA-O
  • 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+1Key: MEANFMOQMXYMCT-IKLDFBCSAN
SMILES
  • O=C(O)C(NC(=O)c1ccc(cc1)N4/C=3/C2=C(/N\C(=N/C2=O)N)NCC3C4)CCC(=O)O
Properties
Chemical formula C20H21N7O6
Molar mass 455.42 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 dehydrogenase. 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.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.

[[File:
FluoropyrimidineActivity_WP1601go to articlego to articlego to articlego to pathway articlego to pathway articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to PubChem Compoundgo to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to pathway articlego to pathway articlego to articlego to articlego to articlego to articlego to articlego to WikiPathwaysgo to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to article
] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ]
FluoropyrimidineActivity_WP1601go to articlego to articlego to articlego to pathway articlego to pathway articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to PubChem Compoundgo to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to pathway articlego to pathway articlego to articlego to articlego to articlego to articlego to articlego to WikiPathwaysgo to articlego to articlego to articlego to articlego to articlego to articlego to articlego to articlego to article
|alt=Fluorouracil (5-FU) Activity edit]] Fluorouracil (5-FU) Activity edit
  1. The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".

References

  1. 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.
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