Dihydrofolic acid

Dihydrofolic acid
Names


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^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:15633^Y
ChEMBL	ChEMBL46294^Y
ChemSpider	89228^Y
ECHA InfoCard	100.116.435
MeSH	dihydrofolate
PubChem	98792
UNII	KXP0KNM559^Y
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
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
Properties
Chemical formula	C₁₉H₂₁N₇O₆
Molar mass	443.414 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Dihydrofolic acid (conjugate base dihydrofolate) (DHF) is a folic acid (vitamin B₉) 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.

Pathway of tetrahydrofolate and antimetabolites

Interactive pathway map

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

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|{{{bSize}}}px|alt=Fluorouracil (5-FU) Activity edit]]

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⁺ Zn²⁺

Base forms

vitamins: see vitamins

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^# B₁ analogues Acefurtiamine Allithiamine Benfotiamine Fursultiamine Octotiamine Prosultiamine Sulbutiamine B₂ Riboflavin^# B₃ Niacin Nicotinamide^# B₅ Pantothenic acid Dexpanthenol Pantethine B₆ Pyridoxine^#, Pyridoxal phosphate Pyridoxamine Pyritinol B₇ Biotin B₉ Folic acid Dihydrofolic acid Folinic acid Levomefolic acid B₁₂ Adenosylcobalamin Cyanocobalamin Hydroxocobalamin Methylcobalamin Choline

C	Ascorbic acid^# Dehydroascorbic acid

Combinations

Multivitamins

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^‡Withdrawn from market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

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