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

• ChemBase ID: 176946
• Molecular Formular: C13H17N5O4
• Molecular Mass: 307.30518
• Monoisotopic Mass: 307.12805405
• SMILES: C1C([C@@H](O[C@@H]1CO)n1c2c(c(ncn2)NC(=O)CC)nc1)O
• Canonical SMILES: OC[C@@H]1CC([C@@H](O1)n1cnc2c1ncnc2NC(=O)CC)O
• InChI: InChI=1S/C13H17N5O4/c1-2-9(21)17-11-10-12(15-5-14-11)18(6-16-10)13-8(20)3-7(4-19)22-13/h5-8,13,19-20H,2-4H2,1H3,(H,14,15,17,21)/t7-,8?,13+/m0/s1
• InChIKey: SPRCIUDOEWOPKD-UBZHVDEJSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 77378-04-2
• PubChem SID: 164232856
• PubChem CID: 46782792

CALCULATED PROPERTIES

• Acid pKa: 11.263646
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.6414275
• LogD (pH = 7.4): -0.6336549
• Log P: -0.633497
• Molar Refractivity: 76.888 cm^3
• Polarizability: 29.468628 Å^3
• Polar Surface Area: 122.39 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P786600

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)