Dihydrofolic acid

Dihydrofolic acid
Skeletal formula of dihydrofolic acid
Space-filling model of the dihydrofolic acid molecule
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.116.435 Edit this at Wikidata
MeSH dihydrofolate
UNII
  • 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 checkY
    Key: OZRNSSUDZOLUSN-LBPRGKRZSA-N checkY
  • 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
  • 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
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).
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Dihydrofolic acid (conjugate base dihydrofolate) (DHF) is a folic acid (vitamin B9) derivative which is converted to tetrahydrofolic acid by dihydrofolate reductase.[1] 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
  1. ^ Maharaj G, Selinsky BS, Appleman JR, Perlman M, London RE, Blakley RL (May 1990). "Dissociation constants for dihydrofolic acid and dihydrobiopterin and implications for mechanistic models for dihydrofolate reductase". Biochemistry. 29 (19): 4554–60. doi:10.1021/bi00471a008. PMID 2372539.