(2R,5S)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 164961
• Molecular Formular: C10H13N5O3
• Molecular Mass: 251.24192
• Monoisotopic Mass: 251.1018393
• SMILES: C1C([C@@H](O[C@@H]1CO)n1c2c(c(ncn2)N)nc1)O
• Canonical SMILES: OC[C@@H]1CC([C@@H](O1)n1cnc2c1ncnc2N)O
• InChI: InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6?,10+/m0/s1
• InChIKey: OFEZSBMBBKLLBJ-GZRQHRFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,5S)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
• Synonyms: 3'-Deoxyadenosine; 9-(3-Deoxy-β-D-ribofuranosyl)adenine; 9-(3-Deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-amine; 9-Cordyceposidoadenine; Cordycepine; NSC 401022; NSC 63984; Cordycepin

Database IDs

• CAS Number: 73-03-0
• PubChem SID: 162259095
• PubChem CID: 46781062

CALCULATED PROPERTIES

• Acid pKa: 13.527495
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.5159566
• LogD (pH = 7.4): -1.4023339
• Log P: -1.4006692
• Molar Refractivity: 62.0985 cm^3
• Polarizability: 23.860285 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 225-226°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C685800

First reported nucleoside antibiotic.

REFERENCES

• Datta, A., et al.: J. Biol. Chem., 262, 5515 (1987)
• Jarvis, M., et al.: J. Pharmacol. Exp. Ther., 295, 1156 (1987)
• Geiser, F., et al.: Mol. Pharmacol., 68, 589 (1987)
• Datta, R., et al.: Biochem. J., 394, 35 (1987)