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

• ChemBase ID: 172255
• Molecular Formular: C22H35N5O4
• Molecular Mass: 433.5444
• Monoisotopic Mass: 433.26890463
• SMILES: C1C([C@@H](O[C@@H]1CO)n1c2c(c(ncn2)NC(=O)CCCCCCCCCCC)nc1)O
• Canonical SMILES: CCCCCCCCCCCC(=O)Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CC1O)CO
• InChI: InChI=1S/C22H35N5O4/c1-2-3-4-5-6-7-8-9-10-11-18(30)26-20-19-21(24-14-23-20)27(15-25-19)22-17(29)12-16(13-28)31-22/h14-17,22,28-29H,2-13H2,1H3,(H,23,24,26,30)/t16-,17?,22+/m0/s1
• InChIKey: SMLBNGQUSUEUEO-LWCIBLMUSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 77378-06-4
• PubChem SID: 164228165
• PubChem CID: 46782049

CALCULATED PROPERTIES

• Acid pKa: 11.260049
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 3.3596945
• LogD (pH = 7.4): 3.3674626
• Log P: 3.367621
• Molar Refractivity: 118.297 cm^3
• Polarizability: 45.946674 Å^3
• Polar Surface Area: 122.39 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L185500

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)