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

• ChemBase ID: 165452
• 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)OC)OC)OC
• Canonical SMILES: O=CN[C@H]1CCc2c(c3c1cc(=O)c(cc3)OC)c(OC)c(c(c2)OC)OC
• InChI: InChI=1S/C21H23NO6/c1-25-17-8-6-13-14(10-16(17)24)15(22-11-23)7-5-12-9-18(26-2)20(27-3)21(28-4)19(12)13/h6,8-11,15H,5,7H2,1-4H3,(H,22,23)/t15-/m0/s1
• InChIKey: HDSXDWASQCHADG-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]formamide
• IUPAC Traditional name: N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]formamide
• Synonyms: N-[(7S)-5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]formamide; Gloriosine; N-Deacetyl-N-formylcolchicine; N-Formyl-N-deacetylcolchicine; N-Formyl-N-desacetylcolchicine; N-Formyldeacetylcolchicine; NSC 403142; N-Deacetyl-N-formyl Colchicine

Database IDs

• CAS Number: 7411-12-3
• PubChem SID: 162259585
• PubChem CID: 23890

CALCULATED PROPERTIES

• Acid pKa: 15.247423
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.4132876
• LogD (pH = 7.4): 1.4132898
• Log P: 1.4132899
• Molar Refractivity: 106.8851 cm^3
• Polarizability: 39.874233 Å^3
• Polar Surface Area: 83.09 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Beige Solid
• Melting Point: 255-258°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D198940

Colchicine (C640000) derivative. A new alkaloid from Gloriosa superba.

REFERENCES

• Reitzer, L., et al.: J. Biol. Chem., 254, 2669 (1979)
• Nadtochiy, S., et al.: Biochem. J., 395, 611 (1979)
• Marroquin, L., et al.: Toxicol. Sci., 97, 539 (1979)