(10S)-3,4,5,14-tetramethoxy-10-(methylamino)tricyclo[9.5.0.02,7]hexadeca-1(16),2,4,6,11,14-hexaen-13-one hydrobromide

• ChemBase ID: 165387
• Molecular Formular: C21H26BrNO5
• Molecular Mass: 452.33884
• Monoisotopic Mass: 451.09943494
• SMILES: c1(c(c(c2c(c1)CC[C@@H](c1c2ccc(c(=O)c1)OC)NC)OC)OC)OC.Br
• Canonical SMILES: CN[C@H]1CCc2c(c3c1cc(=O)c(cc3)OC)c(OC)c(c(c2)OC)OC.Br
• InChI: InChI=1S/C21H25NO5.BrH/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15;/h7,9-11,15,22H,6,8H2,1-5H3;1H/t15-;/m0./s1
• InChIKey: YEUWJSBRIISJLR-RSAXXLAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S)-3,4,5,14-tetramethoxy-10-(methylamino)tricyclo[9.5.0.0^2,^7]hexadeca-1(16),2,4,6,11,14-hexaen-13-one hydrobromide
• IUPAC Traditional name: colcemid hydrobromide
• Synonyms: N-Desacetyl-N-methylcolchicine Hydrobromide Salt; (7S)-6,7-Dihydro-1,2,3,10-tetramethoxy-7-(methylamino)benzo[a]heptalen-9(5H)-one Hydrobromide; Demecolcine Hydrobromide Salt

Database IDs

• CAS Number: 1246817-95-7
• PubChem SID: 162259520
• PubChem CID: 71315175

CALCULATED PROPERTIES

• Acid pKa: 16.95793
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.1205513
• LogD (pH = 7.4): -0.17595741
• Log P: 2.0757225
• Molar Refractivity: 106.7064 cm^3
• Polarizability: 40.089058 Å^3
• Polar Surface Area: 66.02 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichlormethane; DMSO; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D230795

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

• 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)
• Andreu, J.M., et al.: Biochemistry, 37, 8356 (1992)
• Jordan, A., et al.: Med. Res. Rev