2,2,2-trifluoro-N-[(10S)-3,4,5,13-tetramethoxy-14-oxotricyclo[9.5.0.02,7]hexadeca-1(11),2(7),3,5,12,15-hexaen-10-yl]acetamide

• ChemBase ID: 179062
• Molecular Formular: C22H22F3NO6
• Molecular Mass: 453.4083896
• Monoisotopic Mass: 453.13992209
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(=O)c(c1)OC)NC(=O)C(F)(F)F)OC)OC)OC
• Canonical SMILES: COc1cc2[C@H](CCc3c(c2ccc1=O)c(OC)c(c(c3)OC)OC)NC(=O)C(F)(F)F
• InChI: InChI=1S/C22H22F3NO6/c1-29-16-10-13-12(6-8-15(16)27)18-11(5-7-14(13)26-21(28)22(23,24)25)9-17(30-2)19(31-3)20(18)32-4/h6,8-10,14H,5,7H2,1-4H3,(H,26,28)/t14-/m0/s1
• InChIKey: MMPDMRMUKXXBSV-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,2-trifluoro-N-[(10S)-3,4,5,13-tetramethoxy-14-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(11),2(7),3,5,12,15-hexaen-10-yl]acetamide
• IUPAC Traditional name: 2,2,2-trifluoro-N-[(10S)-3,4,5,13-tetramethoxy-14-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(11),2(7),3,5,12,15-hexaen-10-yl]acetamide
• Synonyms: 2,2,2-Trifluoro-N-[(7S)-5,6,7,10-tetrahydro-1,2,3,9-tetramethoxy-10-oxobenzo[a]heptalen-7-yl]acetamide; N-(Trifluoroacetyl)deacetylisocolchicine; N-Trifluoroacetyliso Deacetylcolchicine

Database IDs

• CAS Number: 71324-48-6
• PubChem SID: 164234972
• PubChem CID: 330191

CALCULATED PROPERTIES

• Acid pKa: 5.8381934
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.4524214
• LogD (pH = 7.4): 1.7332226
• Log P: 2.5943172
• Molar Refractivity: 112.3858 cm^3
• Polarizability: 41.074142 Å^3
• Polar Surface Area: 83.09 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichlormethane; DMSO; Ethanol; Ethyl Acetate; Methanol
• Apperance: Tan Solid
• Melting Point: 136-138°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T788100

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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• Ceccatelli, S., et al.: Neuroreport, 8, 3779 (1992)
• 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