5,10-Methylenetetrahydrofolate

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5,10-Methylenetetrahydrofolate

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^Y
PubChem	108194
ChemSpider	97272^Y
MeSH	5,10-methylenetetrahydrofolate
ChEBI	CHEBI:20502^Y
ChEMBL	CHEMBL117348^Y
Jmol-3D images	Image 1
SMILES O=C(O)[C@@H](NC(=O)c1ccc(cc1)N4CC3N(C=2C(=O)/N=C(/N)NC=2NC3)C4)CCC(=O)O
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^Y Key: QYNUQALWYRSVHF-ABLWVSNPSA-N^Y 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
Properties
Molecular formula	C₂₀H₂₃N₇O₆
Molar mass	457.44 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

5,10-Methylenetetrahydrofolate (5,10-CH₂-THF) is the substrate used by the enzyme methylenetetrahydrofolate reductase (MTHFR) 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. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase.

References

Enzyme cofactors

Active forms

vitamins	TPP / ThDP (B₁) · FMN, FAD (B₂) · NAD⁺, NADH, NADP⁺, NADPH (B₃) · Coenzyme A (B₅) · PLP / P5P (B₆) · Biotin (B₇) · THFA / H₄FA, DHFA / H₂FA, MTHF (B₉) · AdoCbl, MeCbl (B₁₂) · Ascorbic Acid (C) · Phylloquinone (K₁), Menaquinone (K₂) · Coenzyme F420

non-vitamins	ATP · CTP · SAMe · PAPS · GSH · Coenzyme B · Cofactor F430 · Coenzyme M · Coenzyme Q · Heme / Haem (A, B, C, O) · Lipoic Acid · Methanofuran · Molybdopterin/Molybdenum cofactor · PQQ · THB / BH₄ · THMPT / H₄MPT

minerals	Ca²⁺ · Cu²⁺ · Fe²⁺, Fe³⁺ · Mg²⁺ · Mn²⁺ · Mo · Ni²⁺ · Se · Zn²⁺

Base forms

vitamins: see vitamins

M: NUT

cof, enz, met

noco, nuvi, sysi/epon, met

drug(A8/11/12)

Vitamins (A11)

Fat soluble

A	α-Carotene · β-Carotene · Retinol^# · Tretinoin

D	D₂ (Ergosterol, Ergocalciferol^#) · D₃ (7-Dehydrocholesterol, Previtamin D₃, Cholecalciferol, 25-hydroxycholecalciferol, Calcitriol (1,25-dihydroxycholecalciferol), Calcitroic acid) · D₄ (Dihydroergocalciferol) · D₅ · D analogues (Dihydrotachysterol, Calcipotriol, Tacalcitol, Paricalcitol)

E	Tocopherol (Alpha, Beta, Gamma, Delta) · Tocotrienol (Alpha, Beta, Gamma, Delta) · Tocofersolan

K	Naphthoquinone · Phylloquinone (K₁) · Menatetrenone (K₂) · Menadione (K₃) · Menadiol (K₄)

Water soluble

B	B₁ (Thiamine^#) · B₂ (Riboflavin^#) · B₃ (Niacin, Nicotinamide^#) · B₅ (Pantothenic acid, Dexpanthenol, Pantethine) · B₆ (Pyridoxine^#, Pyridoxal phosphate, Pyridoxamine) · B₇ (Biotin) · B₉ (Folic acid, Dihydrofolic acid, Folinic acid) · B₁₂ (Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide) · Choline

C	Ascorbic acid^# · Dehydroascorbic acid

Combinations

Multivitamins

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: NUT

cof, enz, met

noco, nuvi, sysi/epon, met

drug(A8/11/12)

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