5,10-Methenyltetrahydrofolate

5,10-Methenyltetrahydrofolate

Names
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
ChEMBL	ChEMBL46521
ChemSpider	133
Jmol interactive 3D	Image
MeSH	5,10-methenyltetrahydrofolate
PubChem	644350
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 Key: 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+1 Key: MEANFMOQMXYMCT-IKLDFBCSAN
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
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 [77 °F], 100 kPa).
verify (what is  ?)
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.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

[[File:

[[<div style="display:block; width:58px; height:0px; overflow:hidden; position:relative; left:174.0px; top:75px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:53px; height:0px; overflow:hidden; position:relative; left:308.0px; top:87px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:53px; height:0px; overflow:hidden; position:relative; left:308.0px; top:67px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:51px; height:0px; overflow:hidden; position:relative; left:72.0px; top:120px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:59px; height:0px; overflow:hidden; position:relative; left:54.0px; top:178px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:80px; height:0px; overflow:hidden; position:relative; left:519.0px; top:112px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:436.5px; top:97px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:436.5px; top:117px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:34px; height:0px; overflow:hidden; position:relative; left:403.0px; top:155px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:46px; height:0px; overflow:hidden; position:relative; left:344.0px; top:130px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:46px; height:0px; overflow:hidden; position:relative; left:344.0px; top:150px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:46px; height:0px; overflow:hidden; position:relative; left:344.0px; top:170px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:39px; height:0px; overflow:hidden; position:relative; left:245.0px; top:352px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:350.0px; top:238px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:440.0px; top:302px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:544.0px; top:301px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:321.0px; top:400px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:46px; height:0px; overflow:hidden; position:relative; left:311.0px; top:310px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:46px; height:0px; overflow:hidden; position:relative; left:311.0px; top:330px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:321.0px; top:420px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:188.0px; top:293px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:188.0px; top:313px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:53.0px; top:326px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:46px; height:0px; overflow:hidden; position:relative; left:75.0px; top:259px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:197.0px; top:448px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:197.0px; top:468px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:208.5px; top:809px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:326.5px; top:566px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:326.5px; top:526px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:326.5px; top:546px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:56px; height:0px; overflow:hidden; position:relative; left:491.0px; top:545px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:163px; height:0px; overflow:hidden; position:relative; left:79.0px; top:866px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:77px; height:0px; overflow:hidden; position:relative; left:164.0px; top:912px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:288.0px; top:854px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:308.0px; top:892px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:80px; height:0px; overflow:hidden; position:relative; left:437.0px; top:816px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:80px; height:0px; overflow:hidden; position:relative; left:389.0px; top:863px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:487.5px; top:842px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:386.5px; top:890px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:430.5px; top:890px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:386.5px; top:910px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:430.5px; top:910px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:180.5px; top:966px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:224.5px; top:966px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:180.5px; top:946px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:44px; height:0px; overflow:hidden; position:relative; left:224.5px; top:946px; background:transparent; border-top:3px blue solid"></div>]]

[[

]]

|{{{bSize}}}px|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.