2-amino-9-[(1R,2S)-2,3-bis(hydroxymethyl)cyclobutyl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 172361
• Molecular Formular: C11H15N5O3
• Molecular Mass: 265.2685
• Monoisotopic Mass: 265.11748937
• SMILES: [nH]1c(nc2c(c1=O)ncn2[C@H]1[C@H](C(C1)CO)CO)N
• Canonical SMILES: OC[C@H]1C(CO)C[C@H]1n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C11H15N5O3/c12-11-14-9-8(10(19)15-11)13-4-16(9)7-1-5(2-17)6(7)3-18/h4-7,17-18H,1-3H2,(H3,12,14,15,19)/t5?,6-,7+/m0/s1
• InChIKey: GWFOVSGRNGAGDL-BOJSHJERSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(1R,2S)-2,3-bis(hydroxymethyl)cyclobutyl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(1R,2S)-2,3-bis(hydroxymethyl)cyclobutyl]-1H-purin-6-one
• Synonyms: 2-Amino-9-[(1R,2R,3S)-2,3-bis(hydroxymethyl)cyclobutyl]-1,9-dihydro-6H-purin-6-one; [1R-(1α,2β,3α)]-2-Amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-1,9-dihydro-6H-purin-6-one; (+)-Cyclobut G; BMS 180194; SQ 34514; Lobucavir

Database IDs

• CAS Number: 127759-89-1
• PubChem SID: 164228271
• PubChem CID: 46782069

CALCULATED PROPERTIES

• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 10.168573
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.1144094
• LogD (pH = 7.4): -2.114965
• Log P: -2.1143126
• Molar Refractivity: 67.4355 cm^3
• Polarizability: 24.597788 Å^3
• Polar Surface Area: 125.76 Å^2

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 284-286°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L469360

A nucleoside analog used in the treatment of viral infections, including those caused by human immunodeficiency virus, cytomegalovirus, and herpes virus.

REFERENCES

• Faulds, D., et al.: Drugs, 39, 597 (1990)
• Greene, J., et al.: Fundam. Appl. Toxicol., 32, 140 (1990)
• Poirier, M., et al.: Toxicol. Appl. Pharmacol., 199, 151 (1990)