Dihydrofolic acid

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	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, 100 kPa)
Infobox references

Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. Since tetrahydrofolate is needed to make both purines and pyrimidines, dihydrofolate reductase is targeted by various drugs to prevent nucleic acid synthesis. Dihydrofolic acid is also known by the name dihydrofolate - more commonly vitamin B₉.

Interactive pathway map

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

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Fluorouracil (5-FU) Activity edit

References

^ The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601". http://www.wikipathways.org/index.php/Pathway:WP1601.

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)