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

• ChemBase ID: 164890
• Molecular Formular: C21H23NO6
• Molecular Mass: 385.41042
• Monoisotopic Mass: 385.15253746
• SMILES: c1c(c(c(c2c1CC[C@@H](c1c2ccc(c(=O)c1)O)NC(=O)C)OC)OC)OC
• Canonical SMILES: COc1c(OC)cc2c(c1OC)c1ccc(c(=O)cc1[C@H](CC2)NC(=O)C)O
• InChI: InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-18(26-2)20(27-3)21(28-4)19(12)13-6-8-16(24)17(25)10-14(13)15/h6,8-10,15H,5,7H2,1-4H3,(H,22,23)(H,24,25)/t15-/m0/s1
• InChIKey: PRGILOMAMBLWNG-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(10S)-14-hydroxy-3,4,5-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)-14-hydroxy-3,4,5-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-10-hydroxy-1,2,3,-trimethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide; O10-Demethylcolchicine; NSC 33411; Colchiceine

Database IDs

• CAS Number: 477-27-0
• PubChem SID: 162259024
• PubChem CID: 234105

CALCULATED PROPERTIES

• Acid pKa: 10.526462
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.3491558
• LogD (pH = 7.4): 1.3488368
• Log P: 1.3491611
• Molar Refractivity: 106.6244 cm^3
• Polarizability: 39.803528 Å^3
• Polar Surface Area: 94.09 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetonitril; DMSO
• Apperance: Off- White to Pale Yellow Solid
• Melting Point: 172-174°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C638500

A metabolite of Colchicine.

REFERENCES

• Zweig, M.H., et al.: Biochem. Pharmacol., 22, 2141 (1973)
• Fitzgerald, T.J., et al.: Biochem. Pharmacol., et al.: 25, 1383, (1973)