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]acetamide

• ChemBase ID: 179055
• Molecular Formular: C21H20F3NO6
• Molecular Mass: 439.3818096
• Monoisotopic Mass: 439.12427203
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(c(=O)c1)O)NC(=O)C(F)(F)F)OC)OC)OC
• Canonical SMILES: COc1c(OC)cc2c(c1OC)c1ccc(c(=O)cc1[C@H](CC2)NC(=O)C(F)(F)F)O
• InChI: InChI=1S/C21H20F3NO6/c1-29-16-8-10-4-6-13(25-20(28)21(22,23)24)12-9-15(27)14(26)7-5-11(12)17(10)19(31-3)18(16)30-2/h5,7-9,13H,4,6H2,1-3H3,(H,25,28)(H,26,27)/t13-/m0/s1
• InChIKey: GZXFPMJSKAABTM-ZDUSSCGKSA-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]acetamide
• 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]acetamide
• Synonyms: 2,2,2-Trifluoro-N-[(7S)-5,6,7,9-tetrahydro-10-hydroxy-1,2,3-trimethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide; (S)-2,2,2-Trifluoro-N-(5,6,7,9-tetrahydro-10-hydroxy-1,2,3-trimethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide; N-Trifluoroacetyl Deacetylcolchiceine

Database IDs

• CAS Number: 71295-34-6
• PubChem SID: 164234965
• PubChem CID: 453133

CALCULATED PROPERTIES

• LogD (pH = 5.5): 2.3215656
• LogD (pH = 7.4): 1.610152
• Log P: 2.48149
• Molar Refractivity: 107.6346 cm^3
• Polarizability: 39.19393 Å^3
• Polar Surface Area: 94.09 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true
• Acid pKa: 5.77322
• H Acceptors: 6
• H Donor: 2

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichlormethane; DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 166-168°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T787015

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