chloromethyl (10S)-10-acetamido-3,5-dimethoxy-14-(methylsulfanyl)-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaene-4-carboxylate

• ChemBase ID: 164087
• Molecular Formular: C23H24ClNO6S
• Molecular Mass: 477.95776
• Monoisotopic Mass: 477.10128617
• SMILES: c12c3c([C@H](CCc1cc(c(c2OC)C(=O)OCCl)OC)NC(=O)C)cc(=O)c(cc3)SC
• Canonical SMILES: ClCOC(=O)c1c(OC)cc2c(c1OC)c1ccc(c(=O)cc1[C@H](CC2)NC(=O)C)SC
• InChI: InChI=1S/C23H24ClNO6S/c1-12(26)25-16-7-5-13-9-18(29-2)21(23(28)31-11-24)22(30-3)20(13)14-6-8-19(32-4)17(27)10-15(14)16/h6,8-10,16H,5,7,11H2,1-4H3,(H,25,26)/t16-/m0/s1
• InChIKey: ZSPDEGWRRUIQQA-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chloromethyl (10S)-10-acetamido-3,5-dimethoxy-14-(methylsulfanyl)-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaene-4-carboxylate
• IUPAC Traditional name: chloromethyl (10S)-10-acetamido-3,5-dimethoxy-14-(methylsulfanyl)-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaene-4-carboxylate
• Synonyms: Chloroacetic Acid (7S)-7-(Acetylamino)-5,6,7,9-tetrahydro-1,3-dimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-2-yl Ester; (S)-2-Chloroacetyl-2-demethyl Thiocolchicine

Database IDs

• CAS Number: 148731-67-3
• PubChem SID: 162258222
• PubChem CID: 46783666

CALCULATED PROPERTIES

• Acid pKa: 14.699775
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.0245886
• LogD (pH = 7.4): 3.02459
• Log P: 3.02459
• Molar Refractivity: 127.6039 cm^3
• Polarizability: 47.872658 Å^3
• Polar Surface Area: 90.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Yellow Crystalline Solid
• Melting Point: 245-250°C dec.

DETAILS

Toronto Research Chemicals - C363400

Has shown anti-tumor activity.

REFERENCES

• Bai, R., et al.: J. Biol. Chem., 275, 40443 (2000)