(2R,3R,4R,5S,6R)-6-{[(10S)-10-acetamido-3,4-dimethoxy-14-(methylsulfanyl)-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 165822
• Molecular Formular: C27H31NO11S
• Molecular Mass: 577.60014
• Monoisotopic Mass: 577.16178182
• SMILES: c1(=O)cc2c(ccc1SC)c1c(CC[C@@H]2NC(=O)C)cc(c(c1OC)OC)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O
• Canonical SMILES: COc1c(O[C@H]2O[C@H](C(=O)O)[C@@H]([C@H]([C@H]2O)O)O)cc2c(c1OC)c1ccc(c(=O)cc1[C@H](CC2)NC(=O)C)SC
• InChI: InChI=1S/C27H31NO11S/c1-11(29)28-15-7-5-12-9-17(38-27-22(33)20(31)21(32)25(39-27)26(34)35)23(36-2)24(37-3)19(12)13-6-8-18(40-4)16(30)10-14(13)15/h6,8-10,15,20-22,25,27,31-33H,5,7H2,1-4H3,(H,28,29)(H,34,35)/t15-,20+,21+,22-,25+,27-/m0/s1
• InChIKey: JJEHAQVFBUIDIV-IMCCAWCASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-{[(10S)-10-acetamido-3,4-dimethoxy-14-(methylsulfanyl)-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-{[(10S)-10-acetamido-3,4-dimethoxy-14-(methylsulfanyl)-13-oxotricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (7S)-7-(Acetylamino)-5,6,7,9-tetrahydro-1,2-dimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-3-yl β-D-Glucopyranosiduronic Acid; 3-Demethyl Thiocolchicine 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 819802-34-1
• PubChem SID: 162259955
• PubChem CID: 71315411

CALCULATED PROPERTIES

• Acid pKa: 2.9423296
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -2.3592527
• LogD (pH = 7.4): -3.3251076
• Log P: 0.15599713
• Molar Refractivity: 144.9319 cm^3
• Polarizability: 55.82104 Å^3
• Polar Surface Area: 181.08 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow SOlid
• Melting Point: >234°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D231335

The major metabolite of Thiocolchicoside (TCC), a muscle relaxant drug.

REFERENCES

• Sandouk, P., et al.: Biopharm. Drug Dispos., 15, 87 (1994)
• Perucca, E., et al.: Eur. J. Drug Metab. Pharmacokinet., 20, 301 (1994)
• Advokat, C., et al.: Pharmacol. Biochem. Behav., 63, 527 (1994)