2-amino-9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 153828
• Molecular Formular: C10H13N5O3
• Molecular Mass: 251.24192
• Monoisotopic Mass: 251.1018393
• SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]1CC[C@H](O1)CO)N
• Canonical SMILES: OC[C@@H]1CC[C@@H](O1)n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H13N5O3/c11-10-13-8-7(9(17)14-10)12-4-15(8)6-2-1-5(3-16)18-6/h4-6,16H,1-3H2,(H3,11,13,14,17)/t5-,6+/m0/s1
• InChIKey: OCLZPNCLRLDXJC-NTSWFWBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: guanosine, 2',3'-dideoxy-
• Synonyms: 2′, 3′-Dideoxyguanosine; 2-Amino-9-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one

Database IDs

• CAS Number: 85326-06-3
• MDL Number: MFCD00057074
• PubChem SID: 162247967
• PubChem CID: 64974

CALCULATED PROPERTIES

• Acid pKa: 10.158622
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.0970316
• LogD (pH = 7.4): -1.0975945
• Log P: -1.0969274
• Molar Refractivity: 62.3165 cm^3
• Polarizability: 22.920849 Å^3
• Polar Surface Area: 114.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 95+%
• Empirical Formula (Hill Notation): C10H13N5O3

DETAILS

Sigma Aldrich - D8691

Application
Metacavir (6-O-methyl-2′, 3′-dideoxyguanosine) is a reverse transcriptase inhibitor with potent activity against hepatitis B virus (HBV); it is a prodrug that is activated in vivo by demethylation and conversion to 2′, 3′-dideoxyguanosine.1