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CHEBI:473990 - entecavir (anhydrous)

ChEBI IDCHEBI:473990
ChEBI Nameentecavir (anhydrous)
Stars
DefinitionGuanine substituted at the 9 position by a 4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl group. A synthetic analogue of 2'-deoxyguanosine, it is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus. Entecavir is phosphorylated intracellularly to the active triphosphate form, which competes with deoxyguanosine triphosphate, the natural substrate of hepatitis B virus reverse transcriptase, inhibiting every stage of the enzyme's activity, although it has no activity against HIV. It is used for the treatment of chronic hepatitis B.
Last Modified22 February 2017
DownloadsMolfile
FormulaC12H15N5O3
Net Charge0
Average Mass277.284
Monoisotopic Mass277.11749
SMILESC=C1[C@H](CO)[C@@H](O)C[C@@H]1n1cnc2c(=O)nc(N)nc21
InChIInChI=1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m0/s1
InChIKeyQDGZDCVAUDNJFG-FXQIFTODSA-N
Roles Classification
Biological Roles:
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor  A DNA polymerase inhibitor that interferes with the activity of reverse transcriptase, EC 2.7.7.49, a viral DNA polymerase enzyme that retroviruses need in order to reproduce.
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
Application:
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
ChEBI Ontology
Outgoing Relation(s)
entecavir (anhydrous) (CHEBI:473990) has role antiviral drug (CHEBI:36044)
entecavir (anhydrous) (CHEBI:473990) has role EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor (CHEBI:59897)
entecavir (anhydrous) (CHEBI:473990) is a 2-aminopurines (CHEBI:20702)
entecavir (anhydrous) (CHEBI:473990) is a oxopurine (CHEBI:25810)
entecavir (anhydrous) (CHEBI:473990) is a primary alcohol (CHEBI:15734)
entecavir (anhydrous) (CHEBI:473990) is a secondary alcohol (CHEBI:35681)
Incoming Relation(s)
entecavir hydrate (CHEBI:59902) has part entecavir (anhydrous) (CHEBI:473990)
IUPAC Name 
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one
INN  Source
entecavirChemIDplus
Manual XrefsDatabases
D07896KEGG DRUG
DB00442DrugBank
LSM-5258LINCS
1019DrugCentral
Registry NumbersSources
Beilstein:7692760Beilstein
CAS:142217-69-4ChemIDplus