N-[(10S)-5-hydroxy-3,4-dimethoxy-14-(methylsulfanyl)-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide

• ChemBase ID: 165820
• Molecular Formular: C21H23NO5S
• Molecular Mass: 401.47602
• Monoisotopic Mass: 401.12969384
• SMILES: c1(=O)cc2c(ccc1SC)c1c(CC[C@@H]2NC(=O)C)cc(c(c1OC)OC)O
• Canonical SMILES: COc1c2c(CC[C@@H](c3c2ccc(c(=O)c3)SC)NC(=O)C)cc(c1OC)O
• InChI: InChI=1S/C21H23NO5S/c1-11(23)22-15-7-5-12-9-17(25)20(26-2)21(27-3)19(12)13-6-8-18(28-4)16(24)10-14(13)15/h6,8-10,15,25H,5,7H2,1-4H3,(H,22,23)/t15-/m0/s1
• InChIKey: PKYOHQGXPPVIGD-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(10S)-5-hydroxy-3,4-dimethoxy-14-(methylsulfanyl)-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide
• IUPAC Traditional name: N-[(10S)-5-hydroxy-3,4-dimethoxy-14-(methylsulfanyl)-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide
• Synonyms: N-[(7S)-5,6,7,9-Tetrahydro-3-hydroxy-1,2-dimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]acetamide; 2-Demethylthio-colchicine; 3-Demethylthiocolchicine; 3-Desmethylthiocolchicine; 3-O-Demethylthiocolchicine; NSC 361792; 3-Demethyl Thiocolchicine

Database IDs

• CAS Number: 87424-25-7
• PubChem SID: 162259953
• PubChem CID: 84076

CALCULATED PROPERTIES

• Acid pKa: 9.9412155
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.1037738
• LogD (pH = 7.4): 2.102552
• Log P: 2.1037908
• Molar Refractivity: 112.9201 cm^3
• Polarizability: 42.175777 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow Solid
• Melting Point: >240°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D231330

A Thiocolchicine metabolite, used in therapy as an antitunor, antiinflammatory and immunosuppressive agent.

REFERENCES

• Trellu, M., et al.: Fund. Clin. Pharmacol., 18, 493 (2004)
• Nakagawa-Goto, K., et al.: Bioorg. Med. Chem. Lett., 15, 235 (2004)
• Gelmi, M., et al.: J. Med. Chem., 50, 2245 (2004)