(2R,3S,5S)-2-(6-amino-9H-purin-9-yl)-5-[hydroxy(13C)methyl](2,3,4,5-13C4)oxolan-3-ol

• ChemBase ID: 164962
• Molecular Formular: C10H13N5O3
• Molecular Mass: 256.20519419
• Monoisotopic Mass: 256.11861349
• SMILES: c12c(ncnc1N)n(cn2)[13C@H]1[13C@H]([13CH2][13C@H](O1)[13CH2]O)O
• Canonical SMILES: O[13CH2][13C@@H]1[13CH2][13C@@H]([13C@@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/i1+1,2+1,5+1,6+1,10+1
• InChIKey: OFEZSBMBBKLLBJ-RWWURRHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5S)-2-(6-amino-9H-purin-9-yl)-5-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-3-ol
• IUPAC Traditional name: (2R,3S,5S)-2-(6-aminopurin-9-yl)-5-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-3-ol
• Synonyms: 3'-Deoxyadenosine-13C5; 9-(3-Deoxy-β-D-ribofuranosyl)adenine-13C5; 9-(3-Deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-amine-13C5; 9-Cordyceposidoadenine-13C5; Cordycepine-13C5; NSC 401022-13C5; NSC 63984-13C5; Cordycepin-13C5

Database IDs

• PubChem SID: 162259096
• PubChem CID: 46781063

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

DETAILS

Toronto Research Chemicals - C685802

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)