CHEBI:2469 - adefovir

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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A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group.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 0
Average Mass 273.186
Monoisotopic Mass 273.063
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.
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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
Manual Xrefs Databases
5HG PDBeChem
Adefovir Wikipedia
C11277 KEGG COMPOUND
D02768 KEGG DRUG
DB00718 DrugBank
View more database links
Registry Numbers Types Sources
106941-25-7 CAS Registry Number KEGG COMPOUND
106941-25-7 CAS Registry Number ChemIDplus
3561094 Beilstein Registry Number ChemIDplus
3561094 Reaxys Registry Number Reaxys
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Last Modified
09 May 2017