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

• ChemBase ID: 165745
• Molecular Formular: C21H23NO6
• Molecular Mass: 385.41042
• Monoisotopic Mass: 385.15253746
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(c(=O)c1)OC)NC(=O)C)OC)O)OC
• Canonical SMILES: COc1ccc2c(cc1=O)[C@H](CCc1c2c(OC)c(c(c1)OC)O)NC(=O)C
• InChI: InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-18(27-3)20(25)21(28-4)19(12)13-6-8-17(26-2)16(24)10-14(13)15/h6,8-10,15,25H,5,7H2,1-4H3,(H,22,23)/t15-/m0/s1
• InChIKey: DPOVAJCRYIUTBD-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(10S)-4-hydroxy-3,5,14-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: N-[(10S)-4-hydroxy-3,5,14-trimethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide
• Synonyms: N-[(7S)-5,6,7,9-Tetrahydro-2-hydroxy-1,3,10-trimethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide; O2-Demethylcolchicine; (-)-2-Demethylcolchicine; NSC 180533; 2-Demethyl Colchicine

Database IDs

• CAS Number: 102491-80-5
• PubChem SID: 162259878
• PubChem CID: 23757

CALCULATED PROPERTIES

• Acid pKa: 7.647434
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.3111593
• LogD (pH = 7.4): 1.123175
• Log P: 1.3160945
• Molar Refractivity: 106.8933 cm^3
• Polarizability: 39.804276 Å^3
• Polar Surface Area: 94.09 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform (Sparingly); Methanol
• Apperance: Yellow Solid
• Melting Point: 166-168°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D230880

A metabolite of Colchicine (C640000). Has shown anti-tumor activity.

REFERENCES

• Martinez, M., et al.: J. Appl. Toxicol., 15, 49 (1995)
• De Vincenzo, R., et al.: Oncol. Res., 11, 145(1995)
• Das, D., et al.: Biochim. Biophys. Acta., 1502, 351 (1995)
• Wagner, B., et al.: J. Biol. Chem., 275, 22461(1995)