N-[(10S)-4-hydroxy-3,5-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: 165819
• Molecular Formular: C21H23NO5S
• Molecular Mass: 401.47602
• Monoisotopic Mass: 401.12969384
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(c(=O)c1)SC)NC(=O)C)OC)O)OC
• Canonical SMILES: COc1c2c(CC[C@@H](c3c2ccc(c(=O)c3)SC)NC(=O)C)cc(c1O)OC
• InChI: InChI=1S/C21H23NO5S/c1-11(23)22-15-7-5-12-9-17(26-2)20(25)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: OMQLBXIHBJAOIO-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(10S)-4-hydroxy-3,5-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)-4-hydroxy-3,5-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-2-hydroxy-1,3-dimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]acetamide; NSC 369937; 2-Demethyl Thiocolchicine

Database IDs

• CAS Number: 87424-26-8
• PubChem SID: 162259952
• PubChem CID: 55708

CALCULATED PROPERTIES

• Acid pKa: 7.647835
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.0963268
• LogD (pH = 7.4): 1.9109738
• Log P: 2.1037908
• Molar Refractivity: 112.9201 cm^3
• Polarizability: 42.17573 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Yellow Crystalline Solid
• Melting Point: 218-220°C

DETAILS

Toronto Research Chemicals - D231325

Has shown anti-tumor activity.