2,2,2-trifluoro-N-methyl-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]acetamide

• ChemBase ID: 179065
• Molecular Formular: C23H24F3NO6
• Molecular Mass: 467.4349696
• Monoisotopic Mass: 467.15557215
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(c(=O)c1)OC)N(C(=O)C(F)(F)F)C)OC)OC)OC
• Canonical SMILES: COc1ccc2c(cc1=O)[C@H](CCc1c2c(OC)c(c(c1)OC)OC)N(C(=O)C(F)(F)F)C
• InChI: InChI=1S/C23H24F3NO6/c1-27(22(29)23(24,25)26)15-8-6-12-10-18(31-3)20(32-4)21(33-5)19(12)13-7-9-17(30-2)16(28)11-14(13)15/h7,9-11,15H,6,8H2,1-5H3/t15-/m0/s1
• InChIKey: HRGYENSCJVMEMY-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,2-trifluoro-N-methyl-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]acetamide
• IUPAC Traditional name: 2,2,2-trifluoro-N-methyl-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]acetamide
• Synonyms: (S)-2,2,2-Trifluoro-N-methyl-N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide; N-(Trifluoroacetyl)demecolchine; N-Trifluoroacetyldemecolcine; NSC 317022; N-Trifluoroacetyl-N-methyl-deacetylcolchicine

Database IDs

• CAS Number: 71295-35-7
• PubChem SID: 164234975
• PubChem CID: 51292

CALCULATED PROPERTIES

• Acid pKa: 17.939444
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.8179932
• LogD (pH = 7.4): 2.8179932
• Log P: 2.8179932
• Molar Refractivity: 117.2825 cm^3
• Polarizability: 42.890163 Å^3
• Polar Surface Area: 74.3 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - T789510

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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• Jordan, A., et al.: Med. Res. Rev
• 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)