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Dihydrofolic acid

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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 InfoCard100.116.435Edit this at Wikidata
MeSHdihydrofolate
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 mass443.414 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Dihydrofolic acid (conjugate basedihydrofolate) (DHF) is afolic acid (vitamin B9) derivative which is converted totetrahydrofolic acid bydihydrofolate reductase.[1] Since tetrahydrofolate is needed to make bothpurines andpyrimidines, which are building blocks ofDNA andRNA, dihydrofolate reductase is targeted by various drugs to preventnucleic acid synthesis.

Pathway of tetrahydrofolate and antimetabolites

Interactive pathway map

[edit]

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

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

Further reading

[edit]
  • Gangjee, Aleem; Jain, Hiteshkumar D.; Kurup, Sonali (2007). "Recent Advances in Classical and Non-Classical Antifolates as Antitumor and Antiopportunistic Infection Agents: Part I".Anti-Cancer Agents in Medicinal Chemistry.7 (5):524–542.doi:10.2174/187152007781668724.PMID 17896913.

References

[edit]
  1. ^Green, Jacalyn M.; Matthews, Rowena G. (2007). "Folate Biosynthesis, Reduction, and Polyglutamylation and the Interconversion of Folate Derivatives".EcoSal Plus.2 (2).doi:10.1128/ecosalplus.3.6.3.6.PMID 26443588.
Active forms
vitamins
non-vitamins
metal ions
Base forms
Fat
soluble
A
D
E
K (B02B)
Water
soluble
B
C
Combinations
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