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 (JSmol)	Interactive image
ChEBI	CHEBI:15633^Y
ChemSpider	89228^Y
ECHA InfoCard	100.116.435
MeSH	dihydrofolate
PubChem CID	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]}

[[File:<div class="noresize thumb tnone" style="; "> <div class="thumbinner" style="overflow:hidden;width:701px;"> <div class="thumbimage" style=" overflow:hidden; position:relative; background-color:white;"> <div style=";left:0px; top:0px; width:699px; position:absolute;"> <imagemap> Image:FluoropyrimidineActivity_WP1601.png|right|alt=FluoropyrimidineActivity_WP1601 rect 174.0 70.0 232.0 90.0 go to article rect 308.0 82.0 361.0 102.0 go to article rect 308.0 62.0 361.0 82.0 go to article rect 224.0 25.0 328.0 45.0 go to pathway article rect 238.0 207.0 289.0 227.0 go to pathway article rect 72.0 115.0 123.0 135.0 go to article rect 54.0 173.0 113.0 193.0 go to article rect 519.0 107.0 599.0 127.0 go to article rect 436.5 92.0 480.5 112.0 go to article rect 436.5 112.0 480.5 132.0 go to article rect 403.0 150.0 437.0 170.0 go to article rect 344.0 125.0 390.0 145.0 go to article rect 344.0 145.0 390.0 165.0 go to article rect 344.0 165.0 390.0 185.0 go to article rect 245.0 347.0 284.0 367.0 go to PubChem Compound rect 350.0 233.0 394.0 253.0 go to article rect 440.0 297.0 484.0 317.0 go to article rect 544.0 296.0 588.0 316.0 go to article rect 321.0 395.0 365.0 415.0 go to article rect 311.0 305.0 357.0 325.0 go to article rect 311.0 325.0 357.0 345.0 go to article rect 321.0 415.0 365.0 435.0 go to article rect 188.0 288.0 232.0 308.0 go to article rect 188.0 308.0 232.0 328.0 go to article rect 53.0 321.0 97.0 341.0 go to article rect 75.0 254.0 121.0 274.0 go to article rect 197.0 443.0 241.0 463.0 go to article rect 197.0 463.0 241.0 483.0 go to article rect 208.5 804.0 252.5 824.0 go to article rect 326.5 561.0 370.5 581.0 go to article rect 326.5 521.0 370.5 541.0 go to article rect 326.5 541.0 370.5 561.0 go to article rect 491.0 540.0 547.0 560.0 go to article rect 414.0 475.0 453.0 495.0 go to pathway article rect 418.0 610.0 457.0 630.0 go to pathway article rect 79.0 861.0 242.0 881.0 go to article rect 164.0 907.0 241.0 927.0 go to article rect 288.0 849.0 332.0 869.0 go to article rect 308.0 887.0 352.0 907.0 go to article rect 437.0 811.0 517.0 831.0 go to article rect 389.0 858.0 469.0 878.0 go to WikiPathways rect 487.5 837.0 531.5 857.0 go to article rect 386.5 885.0 430.5 905.0 go to article rect 430.5 885.0 474.5 905.0 go to article rect 386.5 905.0 430.5 925.0 go to article rect 430.5 905.0 474.5 925.0 go to article rect 180.5 961.0 224.5 981.0 go to article rect 224.5 961.0 268.5 981.0 go to article rect 180.5 941.0 224.5 961.0 go to article rect 224.5 941.0 268.5 961.0 go to article default Go to pathway article desc none </imagemap>

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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

Combinations

Multivitamins

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

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