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

• ChemBase ID: 179064
• Molecular Formular: C22H22F3NO6
• Molecular Mass: 453.4083896
• Monoisotopic Mass: 453.13992209
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(c(=O)c1)O)N(C(=O)C(F)(F)F)C)OC)OC)OC
• Canonical SMILES: COc1c(OC)cc2c(c1OC)c1ccc(c(=O)cc1[C@H](CC2)N(C(=O)C(F)(F)F)C)O
• InChI: InChI=1S/C22H22F3NO6/c1-26(21(29)22(23,24)25)14-7-5-11-9-17(30-2)19(31-3)20(32-4)18(11)12-6-8-15(27)16(28)10-13(12)14/h6,8-10,14H,5,7H2,1-4H3,(H,27,28)/t14-/m0/s1
• InChIKey: BGKNQBHEZDTGMU-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,2-trifluoro-N-[(10S)-14-hydroxy-3,4,5-trimethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]-N-methylacetamide
• IUPAC Traditional name: 2,2,2-trifluoro-N-[(10S)-14-hydroxy-3,4,5-trimethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]-N-methylacetamide
• Synonyms: 2,2,2-Trifluoro-N-methyl-N-[(7S)-5,6,7,9-tetrahydro-10-hydroxy-1,2,3-trimethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide; N-Trifluoroacetyl-N-methyl-deacetylcolchiceine

Database IDs

• CAS Number: 1217782-80-3
• PubChem SID: 164234974
• PubChem CID: 29987738

CALCULATED PROPERTIES

• Acid pKa: 10.098874
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.705155
• LogD (pH = 7.4): 2.7042983
• Log P: 2.7051659
• Molar Refractivity: 112.5313 cm^3
• Polarizability: 41.00742 Å^3
• Polar Surface Area: 85.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloromethane; Dichlormethane; DMSO; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - T789500

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 normal and tumor cell lines and activates the JNK/SAPK signaling pa

REFERENCES

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• 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