5,10-Methylenetetrahydrofolate

5,10-Methylenetetrahydrofolate

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
CAS Number	3432-99-3
3D model (Jmol)	Interactive image
ChEBI	CHEBI:20502
ChEMBL	ChEMBL117348
ChemSpider	97272
MeSH	5,10-methylenetetrahydrofolate
PubChem	108194
InChI 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 Key: QYNUQALWYRSVHF-ABLWVSNPSA-N 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
SMILES O=C(O)[C@@H](NC(=O)c1ccc(cc1)N4CC3N(C=2C(=O)/N=C(/N)NC=2NC3)C4)CCC(=O)O
Properties
Chemical formula	C20H23N7O6
Molar mass	457.44 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

5,10-Methylenetetrahydrofolate (N5,N10-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 hydroxymethyltransferase.

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

• 5,10-Methenyltetrahydrofolate

References

1. "Entrez Gene: MTHFR methylenetetrahydrofolate reductase (NAD(P)H)".
2. Födinger M, Hörl WH, Sunder-Plassmann G (2000). "Molecular biology of 5,10-methylenetetrahydrofolate reductase.". J Nephrol. 13 (1): 20–33. PMID 10720211.