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
ChEMBL	ChEMBL46294^Y
ChemSpider	89228^Y
ECHA InfoCard	100.116.435
MeSH	dihydrofolate
PubChem CID	98792
UNII	KXP0KNM559^Y
CompTox Dashboard (EPA)	DTXSID401027140
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.^[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

Interactive pathway map

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

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|alt=Fluorouracil (5-FU) Activity edit]]

Fluorouracil (5-FU) Activity edit

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

Further reading

• 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

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.