5,10-Methylenetetrahydrofolate

5,10-Methylenetetrahydrofolate: 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).

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.

See also

Serine hydroxymethyltransferase (SHMT)

5,10-Methenyltetrahydrofolate

References

v · d · eEnzyme 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)

v · d · eVitamins (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)

Categories:
Folates
Coenzymes
Biochemistry stubs

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

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Methylenetetrahydrofolate dehydrogenase (NADP+) — Identifiers EC number 1.5.1.5 CAS number 9029 14 5 … Wikipedia
Methylenetetrahydrofolate—tRNA-(uracil-5-)-methyltransferase — (FADH2 oxidizing) Identifiers EC number 2.1.1.74 CAS number 74665 78 4 … Wikipedia
Methylenetetrahydrofolate dehydrogenase (NAD+) — Identifiers EC number 1.5.1.15 CAS number 82062 90 6 … Wikipedia
Methylenetetrahydrofolate reductase (ferredoxin) — Identifiers EC number 1.5.7.1 Databases IntEnz In … Wikipedia
Methylenetetrahydrofolate reductase — methylene tetrahydrofolate reductase [NAD(P)H] Ribbon diagram of the active site of E. coli MTHFR. The flavin cofactor (top) is shown interacting with the bound substrate NADH.[1] … Wikipedia
Methylenetetrahydrofolate-tRNA-(uracil-5-)-methyltransferase — In enzymology, a methylenetetrahydrofolate tRNA (uracil 5 ) methyltransferase (EC number|2.1.1.74) is an enzyme that catalyzes the chemical reaction:5,10 methylenetetrahydrofolate + tRNA containing uridine at position 54 + FADH2 ightleftharpoons… … Wikipedia
methylenetetrahydrofolate dehydrogenase (NADP+) — meth·y·lene·tet·ra·hy·dro·fo·late de·hy·dro·gen·ase (NADP+) (meth″ə lēn tet″rə hi″dro foґlāt de hiґdro jən ās) [EC 1.5.1.5] an enzyme activity of the oxidoreductase class that catalyzes the… … Medical dictionary
methylenetetrahydrofolate reductase [NAD(P)H] — meth·y·lene·tet·ra·hy·dro·fo·late re·duc·tase [NAD(P)H] (meth″ə lēn tet″rə hi″dro foґlāt re dukґtās) [EC 1.5.1.20] an enzyme of the oxidoreductase class that catalyzes the reduction of 5,10… … Medical dictionary
methylenetetrahydrofolate reductase (MTHFR) deficiency — meth·y·lene·tet·ra·hy·dro·fo·late re·duc·tase (MTHFR) de·fi·cien·cy (meth″ə lēn tet″rə hi″dro foґlāt re dukґtās) a common, autosomal recessive, inborn error of folate metabolism caused by mutation in the … Medical dictionary
5,10-Methylenetetrahydrofolate reductase — 5,10 Méthylènetétrahydrofolate réductase MTHFR d E.coli. Image provenant de PDB:1ZPT L’enzyme 5,10 Méthylènetétrahydrofolate réductase est nommé MTHFR. C est un homodimère présent dans le … Wikipédia en Français
5,10-méthylènetétrahydrofolate réductase — MTHFR d E.coli. Image provenant de PDB:1ZPT L’enzyme 5,10 Méthylènetétrahydrofolate réductase est nommé MTHFR. C est un homodimère présent dans le … Wikipédia en Français

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5,10-Methylenetetrahydrofolate

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5,10-Methylenetetrahydrofolate

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