adefovir (CHEBI:2469)

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ChEBI Name	adefovir

ChEBI ID	CHEBI:2469

Definition	A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40188

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Formula

C8H12N5O4P

Net Charge

Average Mass

273.186

Monoisotopic Mass

273.06269

InChI

InChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)

InChIKey

SUPKOOSCJHTBAH-UHFFFAOYSA-N

SMILES

N1(C2=C(C(N)=NC=N2)N=C1)CCOCP(O)(=O)O

Roles Classification
Biological Role(s):	HIV-1 reverse transcriptase inhibitor An entity which inhibits the activity of HIV-1 reverse transcriptase. drug metabolite antiviral drug A substance used in the prophylaxis or therapy of virus diseases. nephrotoxic agent A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals. DNA synthesis inhibitor Any substance that inhibits the synthesis of DNA.

Application(s):	antiviral drug A substance used in the prophylaxis or therapy of virus diseases.

ChEBI Ontology
Outgoing	adefovir (CHEBI:2469) has functional parent adenine (CHEBI:16708) adefovir (CHEBI:2469) has role antiviral drug (CHEBI:36044) adefovir (CHEBI:2469) has role DNA synthesis inhibitor (CHEBI:59517) adefovir (CHEBI:2469) has role drug metabolite (CHEBI:49103) adefovir (CHEBI:2469) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756) adefovir (CHEBI:2469) has role nephrotoxic agent (CHEBI:50909) adefovir (CHEBI:2469) is a 6-aminopurines (CHEBI:20706) adefovir (CHEBI:2469) is a ether (CHEBI:25698) adefovir (CHEBI:2469) is a phosphonic acids (CHEBI:26069) adefovir (CHEBI:2469) is conjugate acid of adefovir(1−) (CHEBI:134512)

Incoming	adefovir pivoxil (CHEBI:31175) has functional parent adefovir (CHEBI:2469) adefovir(1−) (CHEBI:134512) is conjugate base of adefovir (CHEBI:2469)

IUPAC Name

{[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonic acid

Synonyms	Sources
9-(2-(Phosphonomethoxy)ethyl)adenine	ChemIDplus
9-(2-Phosphonylmethoxyethyl)adenine	KEGG COMPOUND
9-(2-Phosphonylmethoxyethyl)adenine	ChemIDplus
Adefovir	KEGG COMPOUND
DRG-0156	ChemIDplus
GS 0393	ChemIDplus
GS 393	ChemIDplus
GS-0393	ChemIDplus
HSDB 8079	ChemIDplus
N-(2-Phosphonylmethoxyethyl)adenine	ChemIDplus
PMEA	KEGG COMPOUND

Last Modified

09 May 2017