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

• ChemBase ID: 165774
• 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)OC)OS(=O)(=O)O
• Canonical SMILES: COc1c(OC)c(cc2c1c1ccc(c(=O)cc1[C@H](CC2)NC(=O)C)OC)OS(=O)(=O)O
• InChI: InChI=1S/C21H23NO9S/c1-11(23)22-15-7-5-12-9-18(31-32(25,26)27)20(29-3)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: CLDGERRECOTNSE-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162259907
• PubChem CID: 71315386

CALCULATED PROPERTIES

• Acid pKa: -1.8749547
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.5356145
• LogD (pH = 7.4): -1.5356176
• Log P: -1.1996793
• Molar Refractivity: 116.8851 cm^3
• Polarizability: 44.61874 Å^3
• Polar Surface Area: 137.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D231015

The sulfate analogue of the 3-O-desmethyl metabolite of Colchicine (C640000).