2-amino-9-[(3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one hydrate

• ChemBase ID: 72594
• Molecular Formular: C12H17N5O4
• Molecular Mass: 295.29448
• Monoisotopic Mass: 295.12805405
• SMILES: n1c([nH]c2c(c1=O)ncn2C1C[C@@H]([C@H](C1=C)CO)O)N.O
• Canonical SMILES: OC[C@@H]1[C@@H](O)CC(C1=C)n1cnc2c1[nH]c(N)nc2=O.O
• 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-JBDQBEHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one hydrate
• IUPAC Traditional name: 2-amino-9-[(3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one hydrate
• Synonyms: Baraclude; Entecavir hydrate

Database IDs

• CAS Number: 209216-23-9
• PubChem SID: 162037519
• PubChem CID: 170342

CALCULATED PROPERTIES

• Acid pKa: 8.0033045
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.4469311
• LogD (pH = 7.4): -1.5362015
• Log P: -1.4446591
• Molar Refractivity: 71.0008 cm^3
• Polarizability: 26.432161 Å^3
• Polar Surface Area: 125.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: hydrate

DETAILS

Selleck Chemicals - S1252

Research Area: Hepatitis B
Biological Activity:
Entecavir hydrate is an oral antiviral drug used in the treatment of hepatitis B infection. Entecavir hydrate is a nucleoside analog (more specifically, a guanine analogue) that inhibits reverse transcription, DNA replication and transcription in the viral replication process. Entecavir hydrate is more efficacious than previous agents used to treat hepatitis B (lamivudine and adefovir). Entecavir hydrate is also indicated for the treatment of chronic hepatitis B in adults with HIV/AIDS infection. However, Entecavir hydrate is not active against HIV. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Entecavi