Dihydrofolic acid

From Wikipedia, the free encyclopedia

Dihydrofolic acid

IUPAC name N-(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid
Other names H₂folate, DH
Identifiers
CAS number	4033-27-6
PubChem	98792
ChemSpider	89228^Y
MeSH	dihydrofolate
ChEBI	CHEBI:15633^Y
ChEMBL	CHEMBL46294^Y
Jmol-3D images	{{#if:O=C(O)[C@@H](NC(=O)c1ccc(cc1)NCC/2=N/C=3C(=O)\N=C(/NC=3NC\2)N)CCC(=O)O\|Image 1
SMILES O=C(O)[C@@H](NC(=O)c1ccc(cc1)NCC/2=N/C=3C(=O)\N=C(/NC=3NC\2)N)CCC(=O)O
InChI InChI=1S/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1^Y Key: OZRNSSUDZOLUSN-LBPRGKRZSA-N^Y InChI=1/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1 Key: OZRNSSUDZOLUSN-LBPRGKRZBB
Properties
Molecular formula	C₁₉H₂₁N₇O₆
Molar mass	443.414 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Dihydrofolic acid (dihydrofolate, vitamin B₉) is a folic acid derivative which is converted to tetrahydrofolic acid by dihydrofolate reductase. Since tetrahydrofolate is needed to make both purines and pyrimidines, which are building blocks of DNA and RNA, dihydrofolate reductase is targeted by various drugs to prevent nucleic acid synthesis.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

[[File:

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

|{{{bSize}}}px]]

Fluorouracil (5-FU) Activity edit

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

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 (Alfacalcidol, Dihydrotachysterol, Calcipotriol, Tacalcitol, Paricalcitol)

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

K	Naphthoquinone · Phylloquinone (K₁) · Menaquinones (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, L-methylfolate) · 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)

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.