CHEBI:473990 - entecavir (anhydrous)

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ChEBI Name entecavir (anhydrous)
ChEBI ID CHEBI:473990
Definition Guanine 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C12H15N5O3
Net Charge 0
Average Mass 277.27920
Monoisotopic Mass 277.11749
InChI InChI=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
InChIKey QDGZDCVAUDNJFG-FXQIFTODSA-N
SMILES Nc1nc2n(cnc2c(=O)[nH]1)[C@H]1C[C@H](O)[C@@H](CO)C1=C
Roles Classification
Biological Role(s): 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(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
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ChEBI Ontology
Outgoing 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 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
entecavir ChemIDplus
Manual Xrefs Databases
1019 DrugCentral
D07896 KEGG DRUG
DB00442 DrugBank
LSM-5258 LINCS
View more database links
Registry Numbers Types Sources
142217-69-4 CAS Registry Number ChemIDplus
7692760 Beilstein Registry Number Beilstein
Last Modified
22 February 2017