CHEBI:59902 - entecavir hydrate

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name entecavir hydrate
ChEBI ID CHEBI:59902
Definition The monohydrate form of entecavir. A synthetic analogue of 2'-deoxyguanosine, entecavir is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus. It 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. Enteclavir is used for the treatment of chronic hepatitis B.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C12H17N5O4
Net Charge 0
Average Mass 295.29450
Monoisotopic Mass 295.128
InChI InChI=1S/C12H15N5O3.H2O/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);1H2/t6-,7-,8-;/m0./s1
InChIKey YXPVEXCTPGULBZ-WQYNNSOESA-N
SMILES O.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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing entecavir hydrate (CHEBI:59902) has part entecavir (anhydrous) (CHEBI:473990)
entecavir hydrate (CHEBI:59902) has role antiviral drug (CHEBI:36044)
entecavir hydrate (CHEBI:59902) has role EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor (CHEBI:59897)
entecavir hydrate (CHEBI:59902) is a hydrate (CHEBI:35505)
IUPAC Name
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one—water (1/1)
Synonyms Sources
9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)guanine monohydrate ChemIDplus
entecavir ChemIDplus
entecavir monohydrate ChEBI
Manual Xrefs Databases
D04008 KEGG DRUG
DB00442 DrugBank
View more database links
Registry Numbers Types Sources
209216-23-9 CAS Registry Number ChemIDplus
209216-23-9 CAS Registry Number KEGG DRUG
Last Modified
29 July 2010