N-[(10S)-3,4-dimethoxy-14-(methylsulfanyl)-13-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]formamide

• ChemBase ID: 166048
• Molecular Formular: C26H31NO10S
• Molecular Mass: 549.59004
• Monoisotopic Mass: 549.1668672
• SMILES: c12c([C@H](CCc3c1c(c(c(c3)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)CO)O)O)O)OC)OC)NC=O)cc(=O)c(cc2)SC
• Canonical SMILES: O=CN[C@H]1CCc2c(c3c1cc(=O)c(cc3)SC)c(OC)c(c(c2)O[C@@H]1O[C@H](CO)[C@H]([C@H]([C@H]1O)O)O)OC
• InChI: InChI=1S/C26H31NO10S/c1-34-24-17(36-26-23(33)22(32)21(31)18(10-28)37-26)8-12-4-6-15(27-11-29)14-9-16(30)19(38-3)7-5-13(14)20(12)25(24)35-2/h5,7-9,11,15,18,21-23,26,28,31-33H,4,6,10H2,1-3H3,(H,27,29)/t15-,18+,21+,22-,23+,26+/m0/s1
• InChIKey: HBTNEQNKAJFDDC-MSNGREAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(10S)-3,4-dimethoxy-14-(methylsulfanyl)-13-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[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-dimethoxy-14-(methylsulfanyl)-13-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]formamide
• Synonyms: N-[(7S)-3-(β-D-Glucopyranosyloxy)-5,6,7,9-tetrahydro-1,2-dimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]formamide; N-Desacetyl-N-formyl Thiocolchicoside

Database IDs

• CAS Number: 219547-29-2
• PubChem SID: 162260181
• PubChem CID: 71315528

CALCULATED PROPERTIES

• Acid pKa: 12.199406
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.21297845
• LogD (pH = 7.4): -0.21298303
• Log P: -0.21297611
• Molar Refractivity: 140.574 cm^3
• Polarizability: 54.03408 Å^3
• Polar Surface Area: 164.01 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D288410

An alkaloid from colchicine derivative.

REFERENCES

• Kintz, P., et al.: J. Anal. Toxicol., 1997, 21, 70 (1997)
• Shi, Q., et al.: J. Med. Chem., 40, 961 (1997)