[(10S)-10-acetamido-3,5,14-trimethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-4-yl]oxidanesulfonic acid

• ChemBase ID: 165773
• Molecular Formular: C21H23NO9S
• Molecular Mass: 465.47362
• Monoisotopic Mass: 465.10935232
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(c(=O)c1)OC)NC(=O)C)OC)OS(=O)(=O)O)OC
• Canonical SMILES: COc1ccc2c(cc1=O)[C@H](CCc1c2c(OC)c(c(c1)OC)OS(=O)(=O)O)NC(=O)C
• InChI: InChI=1S/C21H23NO9S/c1-11(23)22-15-7-5-12-9-18(29-3)20(31-32(25,26)27)21(30-4)19(12)13-6-8-17(28-2)16(24)10-14(13)15/h6,8-10,15H,5,7H2,1-4H3,(H,22,23)(H,25,26,27)/t15-/m0/s1
• InChIKey: WOOCBMNRNKYWSA-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(10S)-10-acetamido-3,5,14-trimethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-4-yl]oxidanesulfonic acid
• IUPAC Traditional name: [(10S)-10-acetamido-3,5,14-trimethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-4-yl]oxidanesulfonic acid
• Synonyms: N-[(7S)-5,6,7,9-Tetrahydro-2-sulfooxy-1,3,10-trimethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide; 2-Demethyl Colchicine 2-O-Sulfate

Database IDs

• PubChem SID: 162259906
• PubChem CID: 71315385

CALCULATED PROPERTIES

• Acid pKa: -1.9606807
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.5356153
• LogD (pH = 7.4): -1.5356176
• Log P: -1.2635304
• Molar Refractivity: 116.8851 cm^3
• Polarizability: 44.61895 Å^3
• Polar Surface Area: 137.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D231010

The sulfate analogue of the 2-O-desmethyl metabolite of Colchicine (C640000).