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^N
3D model (JSmol)	Interactive image
ChemSpider	133^Y
MeSH	5,10-methenyltetrahydrofolate
PubChem CID	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^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
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).
N verify (what is ^YN ?)
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 class="noresize thumb tnone" style="; "> <div class="thumbinner" style="overflow:hidden;width:701px;"> <div class="thumbimage" style=" overflow:hidden; position:relative; background-color:white;"> <div style=";left:0px; top:0px; width:699px; position:absolute;"> <imagemap> Image:FluoropyrimidineActivity_WP1601.png|right|alt=FluoropyrimidineActivity_WP1601 rect 174.0 70.0 232.0 90.0 go to article rect 308.0 82.0 361.0 102.0 go to article rect 308.0 62.0 361.0 82.0 go to article rect 224.0 25.0 328.0 45.0 go to pathway article rect 238.0 207.0 289.0 227.0 go to pathway article rect 72.0 115.0 123.0 135.0 go to article rect 54.0 173.0 113.0 193.0 go to article rect 519.0 107.0 599.0 127.0 go to article rect 436.5 92.0 480.5 112.0 go to article rect 436.5 112.0 480.5 132.0 go to article rect 403.0 150.0 437.0 170.0 go to article rect 344.0 125.0 390.0 145.0 go to article rect 344.0 145.0 390.0 165.0 go to article rect 344.0 165.0 390.0 185.0 go to article rect 245.0 347.0 284.0 367.0 go to PubChem Compound rect 350.0 233.0 394.0 253.0 go to article rect 440.0 297.0 484.0 317.0 go to article rect 544.0 296.0 588.0 316.0 go to article rect 321.0 395.0 365.0 415.0 go to article rect 311.0 305.0 357.0 325.0 go to article rect 311.0 325.0 357.0 345.0 go to article rect 321.0 415.0 365.0 435.0 go to article rect 188.0 288.0 232.0 308.0 go to article rect 188.0 308.0 232.0 328.0 go to article rect 53.0 321.0 97.0 341.0 go to article rect 75.0 254.0 121.0 274.0 go to article rect 197.0 443.0 241.0 463.0 go to article rect 197.0 463.0 241.0 483.0 go to article rect 208.5 804.0 252.5 824.0 go to article rect 326.5 561.0 370.5 581.0 go to article rect 326.5 521.0 370.5 541.0 go to article rect 326.5 541.0 370.5 561.0 go to article rect 491.0 540.0 547.0 560.0 go to article rect 414.0 475.0 453.0 495.0 go to pathway article rect 418.0 610.0 457.0 630.0 go to pathway article rect 79.0 861.0 242.0 881.0 go to article rect 164.0 907.0 241.0 927.0 go to article rect 288.0 849.0 332.0 869.0 go to article rect 308.0 887.0 352.0 907.0 go to article rect 437.0 811.0 517.0 831.0 go to article rect 389.0 858.0 469.0 878.0 go to WikiPathways rect 487.5 837.0 531.5 857.0 go to article rect 386.5 885.0 430.5 905.0 go to article rect 430.5 885.0 474.5 905.0 go to article rect 386.5 905.0 430.5 925.0 go to article rect 430.5 905.0 474.5 925.0 go to article rect 180.5 961.0 224.5 981.0 go to article rect 224.5 961.0 268.5 981.0 go to article rect 180.5 941.0 224.5 961.0 go to article rect 224.5 941.0 268.5 961.0 go to article default Go to pathway article desc none </imagemap>

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|{{{bSize}}}px|alt=Fluorouracil (5-FU) Activity edit]]

Fluorouracil (5-FU) Activity edit

↑ The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".

References

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

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