N-{9-[(2R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}octanamide

• ChemBase ID: 175786
• Molecular Formular: C18H27N5O4
• Molecular Mass: 377.43808
• Monoisotopic Mass: 377.20630437
• SMILES: C1C([C@@H](O[C@@H]1CO)n1c2c(c(ncn2)NC(=O)CCCCCCC)nc1)O
• Canonical SMILES: CCCCCCCC(=O)Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CC1O)CO
• InChI: InChI=1S/C18H27N5O4/c1-2-3-4-5-6-7-14(26)22-16-15-17(20-10-19-16)23(11-21-15)18-13(25)8-12(9-24)27-18/h10-13,18,24-25H,2-9H2,1H3,(H,19,20,22,26)/t12-,13?,18+/m0/s1
• InChIKey: QCOORYDEEUDEJJ-TWZXDDCKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{9-[(2R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}octanamide
• IUPAC Traditional name: N-{9-[(2R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl}octanamide
• Synonyms: 3'-Deoxy-N-(1-oxooctyl)adenosine; N6-Octanoyl-3'-deoxyadenosine; N6-Octanoyl Cordycepin

Database IDs

• CAS Number: 77378-05-3
• PubChem SID: 164231696
• PubChem CID: 46782608

CALCULATED PROPERTIES

• Acid pKa: 11.260049
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 1.5814198
• LogD (pH = 7.4): 1.589188
• Log P: 1.5893463
• Molar Refractivity: 99.893 cm^3
• Polarizability: 38.610306 Å^3
• Polar Surface Area: 122.39 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O238300

A novel N6-substituted Cordycepin derivative; an adenosine deaminase inhibitor.

REFERENCES

• Johns, D., et al.: Biochem. Pharmacol., 25, 1441 (1976)
• Muller, W., et al.: Cancer Res., 37, 3824 (1976)
• Sugar, A., et al.: Antimicrob. Agents Chemother., 42, 1424 (1976)
• Zhou, X., et al.: Eur. J. Pharmacol., 453, 309 (1976)