2-Amino-9-((1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl)-1,9-dihydro-purin-6-one

ID: ALA5314362

Chembl Id: CHEMBL5314362

Max Phase: Approved

First Approval: 2005

Molecular Formula: C12H17N5O4

Molecular Weight: 277.28

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Entecavir | Entecavir hydrate | Entecavir monohydrate | BMS-200475-01 | SQ-34676 | SQ34676

Trade Names(3): Baraclude | Entecavir | Entecavir mylan

Canonical SMILES:  C=C1[C@H](CO)[C@@H](O)C[C@@H]1n1cnc2c(=O)[nH]c(N)nc21.O

Standard 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

Standard InChI Key:  YXPVEXCTPGULBZ-WQYNNSOESA-N

Associated Targets(Human)

HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CEM-SS (2428 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HFF (3142 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
WI-38 (2654 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Huh-7 (12904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 2.2.15 (869 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB11 Tchem Bile salt export pump (2311 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Hepatitis B virus (7925 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Woodchuck hepatitis virus (122 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Human immunodeficiency virus 1 (70413 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Human immunodeficiency virus (3636 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HBV genotype D (137 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HBcAg Core antigen (581 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: YesChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: Yes
Chirality: YesAvailability: YesProdrug: Yes

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 277.28Molecular Weight (Monoisotopic): 277.1175AlogP: -0.83#Rotatable Bonds: 2
Polar Surface Area: 130.05Molecular Species: NEUTRALHBA: 7HBD: 4
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: 10.17CX Basic pKa: 0.74CX LogP: -1.96CX LogD: -1.96
Aromatic Rings: 2Heavy Atoms: 20QED Weighted: 0.53Np Likeness Score: 1.03

References

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