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

• ChemBase ID: 165732
• Molecular Formular: C20H23NO5
• Molecular Mass: 357.40032
• Monoisotopic Mass: 357.15762284
• SMILES: c1(c(c(c2c(c1)CC[C@@H](c1c2ccc(c(=O)c1)O)NC)OC)OC)OC
• Canonical SMILES: CN[C@H]1CCc2c(c3c1cc(=O)c(cc3)O)c(OC)c(c(c2)OC)OC
• InChI: InChI=1S/C20H23NO5/c1-21-14-7-5-11-9-17(24-2)19(25-3)20(26-4)18(11)12-6-8-15(22)16(23)10-13(12)14/h6,8-10,14,21H,5,7H2,1-4H3,(H,22,23)/t14-/m0/s1
• InChIKey: ATWWYGQDYGSWQA-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S)-14-hydroxy-3,4,5-trimethoxy-10-(methylamino)tricyclo[9.5.0.0^2,^7]hexadeca-1(16),2,4,6,11,14-hexaen-13-one
• IUPAC Traditional name: (10S)-14-hydroxy-3,4,5-trimethoxy-10-(methylamino)tricyclo[9.5.0.0^2,^7]hexadeca-1(16),2,4,6,11,14-hexaen-13-one
• Synonyms: (7S)-6,7-Dihydro-10-hydroxy-1,2,3-trimethoxy-7-(methylamino)-benzo[a]heptalen-9(5H)-one; 7-Deacetamido-7-(methylamino)colchiceine; N-Desacetyl-N-methylcolchiceine; NSC 36559; Demecolceine

Database IDs

• CAS Number: 518-11-6
• PubChem SID: 162259865
• PubChem CID: 235315

CALCULATED PROPERTIES

• Acid pKa: 9.616167
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.2333548
• LogD (pH = 7.4): -0.2889623
• Log P: 1.6755071
• Molar Refractivity: 101.9552 cm^3
• Polarizability: 38.178032 Å^3
• Polar Surface Area: 77.02 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichlormethane; DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 120-122°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D230750

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