2-amino-9-[(1S,3R,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro(4,6-13C2,7-15N)-1H-purin-6-one

• ChemBase ID: 168007
• Molecular Formular: C12H15N5O3
• Molecular Mass: 280.25791857
• Monoisotopic Mass: 280.12123393
• SMILES: [nH]1c(n[13c]2c([13c]1=O)[15n]cn2[C@H]1C[C@H]([C@H](C1=C)CO)O)N
• Canonical SMILES: OC[C@@H]1[C@H](O)C[C@@H](C1=C)n1c[15n]c2[13c]1nc(N)[nH][13c]2=O
• 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/i10+1,11+1,14+1
• InChIKey: QDGZDCVAUDNJFG-PUSDEWLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(1S,3R,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro(4,6-^1^3C₂,7-^1^5N)-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(1S,3R,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl](4,6-^1^3C₂,7-^1^5N)-1H-purin-6-one
• Synonyms: 2-Amino-9-[4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one-13C2,15N; Baraclude-13C2,15N; BMS 200475-13C2,15N; SQ 34676-13C2,15N; Entecavir-13C2,15N

Database IDs

• PubChem SID: 162262139
• PubChem CID: 71316333

CALCULATED PROPERTIES

• Acid pKa: 10.16698
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.9623985
• LogD (pH = 7.4): -1.9629238
• Log P: -1.96227
• Molar Refractivity: 71.4342 cm^3
• Polarizability: 26.239368 Å^3
• Polar Surface Area: 125.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: >215°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E558902

Labelled Entecavir. An oral antiviral drug used in the treatment of hepatitis B infection. A guanine analogue that inhhibits all three steps in the viral replication process.

REFERENCES

• Innaimo, S.F., et al.: Antimicrob. Agents Chemother., 41, 1444 (1997)
• Honkoop, P., et al.: Expert Opin. Invest. Drugs, 12, 683 (1997)
• Chang, T.-T., et al.: N. Engl. J. Med., 354, 1001 (1997)