(1S,13R)-10-(cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one

• ChemBase ID: 172058
• Molecular Formular: C18H23NO2
• Molecular Mass: 285.38072
• Monoisotopic Mass: 285.17287898
• SMILES: c1(cc2c(cc1)C(=O)C1[C@@H]([C@@]2(CCN1CC1CC1)C)C)O
• Canonical SMILES: Oc1ccc2c(c1)[C@@]1(C)CCN(C(C2=O)[C@@H]1C)CC1CC1
• InChI: InChI=1S/C18H23NO2/c1-11-16-17(21)14-6-5-13(20)9-15(14)18(11,2)7-8-19(16)10-12-3-4-12/h5-6,9,11-12,16,20H,3-4,7-8,10H2,1-2H3/t11-,16?,18-/m0/s1
• InChIKey: HQBZLVPZOGIAIQ-GQWBRKQSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,13R)-10-(cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-8-one
• IUPAC Traditional name: (1S,13R)-10-(cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-8-one
• Synonyms: (2S,6R,11R)-3-(Cyclopropylmethyl)-3,4,5,6-tetrahydro-8-hydroxy-6,11-dimethyl-2,6-methano-3-benzazocin-1(2H)-one; Ketazocine; Ketocyclazocine; MCV 4513; NIH 10451; NIH 8847; Win 34276; l-Ketocyclazocine; (-)-Keto Cyclazocine

Database IDs

• CAS Number: 36292-69-0
• PubChem SID: 164227968
• PubChem CID: 44380980

CALCULATED PROPERTIES

• Acid pKa: 7.843858
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3047663
• LogD (pH = 7.4): 2.6232882
• Log P: 2.5174344
• Molar Refractivity: 83.2323 cm^3
• Polarizability: 32.419235 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K187500

A kappa receptor agonist for the treatment of Crohn's disease and the symptoms associated with Crohn's disease.

REFERENCES

• Cheng, Y., et al.: Biochem. Pharmacol., 22, 3099 (1973)
• Wentland, M., et al.: Bioorg. Med. Chem. Lett., 11, 623 (1973)
• Zhang, A., et al.: J. Med. Chem., 47, 165 (1973)