3-(methanesulfonylsulfanyl)-N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]propanamide

• ChemBase ID: 164945
• Molecular Formular: C24H29NO8S2
• Molecular Mass: 523.61896
• Monoisotopic Mass: 523.13345889
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(c(=O)c1)OC)NC(=O)CCSS(=O)(=O)C)OC)OC)OC
• Canonical SMILES: COc1ccc2c(cc1=O)[C@H](CCc1c2c(OC)c(c(c1)OC)OC)NC(=O)CCSS(=O)(=O)C
• InChI: InChI=1S/C24H29NO8S2/c1-30-19-9-7-15-16(13-18(19)26)17(25-21(27)10-11-34-35(5,28)29)8-6-14-12-20(31-2)23(32-3)24(33-4)22(14)15/h7,9,12-13,17H,6,8,10-11H2,1-5H3,(H,25,27)/t17-/m0/s1
• InChIKey: KZMCZFBQMMHSRF-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(methanesulfonylsulfanyl)-N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]propanamide
• IUPAC Traditional name: 3-(methanesulfonylsulfanyl)-N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]propanamide
• Synonyms: Colchicine Methanethiosulfonate

Database IDs

• CAS Number: 1217821-52-7
• PubChem SID: 162259079
• PubChem CID: 29976389

CALCULATED PROPERTIES

• Acid pKa: 14.720275
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.3128611
• LogD (pH = 7.4): 1.3128616
• Log P: 1.3128616
• Molar Refractivity: 137.0286 cm^3
• Polarizability: 52.7565 Å^3
• Polar Surface Area: 117.23 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMF; DMSO; Ethanol; Ethyl Acetate; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 119-120°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C640030

The methanethiosulfonate derfivative of Colchicine (C640000), an antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several norma

REFERENCES

• Lunduena, R.F., et al.: Curr. Opin. Cell Biol., 4, 53 (1992)
• Ceccatelli, S., et al.: Neuroreport, 8, 3779 (1992)
• Want, T.H., et al.: J. Biol. Chem., 273, 4928 (1992)
• Andreu, J.M., et al.: Biochemistry, 37, 8356 (1992)
• Jordan, A., et al.: Med. Res. Rev