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CHEBI:59902 - entecavir hydrate

ChEBI IDCHEBI:59902
ChEBI Nameentecavir hydrate
Stars
DefinitionThe 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.
Last Modified29 July 2010
SubmitterGareth Owen
DownloadsMolfile
FormulaC12H15N5O3.H2O
Net Charge0
Average Mass295.299
Monoisotopic Mass295.12805
SMILESC=C1[C@H](CO)[C@@H](O)C[C@@H]1n1cnc2c(=O)nc(N)nc21.O
InChIInChI=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
InChIKeyYXPVEXCTPGULBZ-WQYNNSOESA-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 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  Source
entecavir monohydrateChEBI
entecavirChemIDplus
9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)guanine monohydrateChemIDplus
Manual XrefsDatabases
D04008KEGG DRUG
DB00442DrugBank
Registry NumbersSources
CAS:209216-23-9KEGG DRUG
CAS:209216-23-9ChemIDplus