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](2H3)acetamide

• ChemBase ID: 178534
• Molecular Formular: C27H33NO10S
• Molecular Mass: 563.61662
• Monoisotopic Mass: 563.18251726
• SMILES: c1(=O)cc2c(ccc1SC)c1c(CC[C@@H]2NC(=O)C)cc(c(c1OC)OC)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc3CC[C@@H](c4c(c3c(c2OC)OC)ccc(c(=O)c4)SC)NC(=O)C)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H33NO10S/c1-12(30)28-16-7-5-13-9-18(37-27-24(34)23(33)22(32)19(11-29)38-27)25(35-2)26(36-3)21(13)14-6-8-20(39-4)17(31)10-15(14)16/h6,8-10,16,19,22-24,27,29,32-34H,5,7,11H2,1-4H3,(H,28,30)/t16-,19+,22+,23-,24+,27+/m0/s1
• InChIKey: LEQAKWQJCITZNK-AXHKHJLKSA-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](^2H₃)acetamide
• 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](^2H₃)acetamide
• Synonyms: N-[(7S)-3-(β-D-Glucopyranosyloxy)-5,6,7,9-tetrahydro-1,2-dimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]acetamide-d3; (S)-N-[3-(β-D-Glucopyranosyloxy)-5,6,7,9-tetrahydro-1,2-dimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]acetamide-d3; Coltramyl-d3; Coltrax-d3; Miorel-d3; Miotens-d3; Muscoril-d3; NSC 147755-d3; Thiocolchicoside-d3

Database IDs

• PubChem SID: 164234444
• PubChem CID: 71752520

CALCULATED PROPERTIES

• Acid pKa: 12.199066
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.16427875
• LogD (pH = 7.4): -0.1642843
• Log P: -0.1642774
• Molar Refractivity: 145.0645 cm^3
• Polarizability: 55.862545 Å^3
• Polar Surface Area: 164.01 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T344387

A labelled GABA receptor antagonist which is prescribed as a muscle relaxant having analgesic effects.

REFERENCES

• Gelmi, M., et al.: J. Med. Chem., 50, 2245 (2007)
• Mascia, M., et al.: Eur. J. Pharmacol., 558, 37 (2007)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2007)