N-[(10S)-14-(2H3)methoxy-3,4,5-trimethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl](2H3)acetamide

• ChemBase ID: 164894
• Molecular Formular: C22H25NO6
• Molecular Mass: 399.437
• Monoisotopic Mass: 399.16818753
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(c(=O)c1)OC)NC(=O)C)OC)OC)OC
• Canonical SMILES: COc1c(OC)cc2c(c1OC)c1ccc(c(=O)cc1[C@H](CC2)NC(=O)C)OC
• InChI: InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1
• InChIKey: IAKHMKGGTNLKSZ-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(10S)-14-(^2H₃)methoxy-3,4,5-trimethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl](^2H₃)acetamide
• IUPAC Traditional name: N-[(10S)-14-(^2H₃)methoxy-3,4,5-trimethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl](^2H₃)acetamide
• Synonyms: N-[(7S)-5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide-d6; (-)-Colchicine-d6; Colchineos-d6; Colchisol-d6; Colcin-d6; Colsaloid-d6; Condylon-d6; NSC 757-d6; Colchicine-d6

Database IDs

• PubChem SID: 162259028
• PubChem CID: 45038708

CALCULATED PROPERTIES

• Acid pKa: 15.057998
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.4619873
• LogD (pH = 7.4): 1.4619886
• Log P: 1.4619886
• Molar Refractivity: 111.3756 cm^3
• Polarizability: 41.70993 Å^3
• Polar Surface Area: 83.09 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Light-Yellow Solid
• Melting Point: 153-155°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C640003

An isotopically labelled 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

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