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

• ChemBase ID: 178535
• Molecular Formular: C22H25NO5S
• Molecular Mass: 415.5026
• Monoisotopic Mass: 415.14534391
• SMILES: c12c([C@H](CCc3c1c(c(c(c3)OC)OC)OC)NC(=O)C)cc(=O)c(cc2)SC
• Canonical SMILES: COc1c2c(CC[C@@H](c3c2ccc(c(=O)c3)SC)NC(=O)C)cc(c1OC)OC
• InChI: InChI=1S/C22H25NO5S/c1-12(24)23-16-8-6-13-10-18(26-2)21(27-3)22(28-4)20(13)14-7-9-19(29-5)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1
• InChIKey: CMEGANPVAXDBPL-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(10S)-3,4,5-trimethoxy-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)-3,4,5-trimethoxy-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-1,2,3-trimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]acetamide; 10-Thio-colchicine; 10-Demethoxy-10-(methylthio)colchicine; NSC 186301; Thiocolchicine

Database IDs

• CAS Number: 2730-71-4
• PubChem SID: 164234445
• PubChem CID: 17648

CALCULATED PROPERTIES

• Acid pKa: 15.078297
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.2496834
• LogD (pH = 7.4): 2.2496848
• Log P: 2.2496848
• Molar Refractivity: 117.4024 cm^3
• Polarizability: 44.084446 Å^3
• Polar Surface Area: 73.86 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Bright Yellow Solid
• Melting Point: 154-158°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T344390

A muscle relaxant.

REFERENCES

• Sharma, S., et al.: Biochem., 49, 2932 (2010)
• Bartusik, D., et al.: Bioorg. Chem., 38, 1 (2010)
• Passarella, D., et al.: Eur. J. Med. Chem., 45, 219 (2010)