5,10-Methylenetetrahydrofolate

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5,10-Methylenetetrahydrofolate
5,10-methylenetetrahydrofolic acid.svg
Names
IUPAC name
N-[4-(3-amino-1-oxo-1,4,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-L-glutamic acid
Other names
5,10-CH2-THF,
MTHF
Identifiers
3432-99-3 N
ChEBI CHEBI:20502 YesY
ChEMBL ChEMBL117348 YesY
ChemSpider 97272 YesY
Jmol 3D model Interactive image
MeSH 5,10-methylenetetrahydrofolate
PubChem 108194
  • InChI=1S/C20H23N7O6/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/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12?,13-/m0/s1 YesY
    Key: QYNUQALWYRSVHF-ABLWVSNPSA-N YesY
  • InChI=1/C20H23N7O6/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/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12?,13-/m0/s1
    Key: QYNUQALWYRSVHF-ABLWVSNPBB
  • O=C(O)[C@@H](NC(=O)c1ccc(cc1)N4CC3N(C=2C(=O)/N=C(/N)NC=2NC3)C4)CCC(=O)O
Properties
C20H23N7O6
Molar mass 457.44 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

5,10-Methylenetetrahydrofolate (5,10-CH2-THF) is the substrate used by the enzyme methylenetetrahydrofolate reductase (MTHFR)[1][2] to generate 5-methyltetrahydrofolate (5-MTHF, or levomefolic acid).

5,10-CH2-THF can also be used as a coenzyme in the biosynthesis of thymidine. To be specific, it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a cofactor in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase.

MTHFR metabolism: folate cycle, methionine cycle, trans-sulfuration and hyperhomocysteinemia. 5-MTHF: 5-methyltetrahydrofolate; 5,10-methyltetrahydrofolate; BAX: Bcl-2-associated X protein; BHMT: betaine-homocysteine S-methyltransferase; CBS: cystathionine beta synthase; CGL: cystathionine gamma-lyase; DHF: dihydrofolate (vitamin B9); DMG: dimethylglycine; dTMP: thymidine monophosphate; dUMP: deoxyuridine monophosphate; FAD+ flavine adenine dicucleotide; FTHF: 10-formyltetrahydrofolate; MS: methionine synthase; MTHFR: mehtylenetetrahydrofolate reductase; SAH: S-adenosyl-L-homocysteine; SAME: S-adenosyl-L-methionine; THF: tetrahydrofolate.

See also

References

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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