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 ;
3D model ( JSmol)	Interactive image;
ChEBI	CHEBI:15633 ;
ChEMBL	ChEMBL46294 ;
ChemSpider	89228 ;
ECHA InfoCard	100.116.435
MeSH	dihydrofolate
PubChem CID	98792;
UNII	KXP0KNM559 ;
	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 Key: OZRNSSUDZOLUSN-LBPRGKRZSA-N ; 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). verify ( what is ?) 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.

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 ]]

Fluorouracil (5-FU) Activity

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

References

^ 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.

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

[WikiPathways-2] The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".

[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.

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[§ 1]

Interactive pathway map

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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
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