(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(6S)-6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 177625
• Molecular Formular: C25H33NO7S
• Molecular Mass: 491.59702
• Monoisotopic Mass: 491.1977734
• SMILES: c1cc(c2c(c1)C[C@H](CC2)N(CCc1cccs1)CCC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CCCN([C@H]1CCc2c(C1)cccc2O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CCc1cccs1
• InChI: InChI=1S/C25H33NO7S/c1-2-11-26(12-10-17-6-4-13-34-17)16-8-9-18-15(14-16)5-3-7-19(18)32-25-22(29)20(27)21(28)23(33-25)24(30)31/h3-7,13,16,20-23,25,27-29H,2,8-12,14H2,1H3,(H,30,31)/t16-,20-,21-,22+,23-,25+/m0/s1
• InChIKey: KIZPMKLPMDPLQT-JUHHHSNRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(6S)-6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(6S)-6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (S)-5,6,7,8-Tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-1-naphthalenyl β-D-Glucopyranosiduronic Acid; Rotigotine β-D-Glucuronide

Database IDs

• CAS Number: 128464-29-9
• PubChem SID: 164233535
• PubChem CID: 71752119

CALCULATED PROPERTIES

• Acid pKa: 3.186998
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.56891054
• LogD (pH = 7.4): 0.5704234
• Log P: 0.57052064
• Molar Refractivity: 126.5697 cm^3
• Polarizability: 49.853035 Å^3
• Polar Surface Area: 119.69 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R700710

Rotigotine β-D-Glucuronide is a metabolite of Rotigotine (R700700).

REFERENCES

• Braun, M., et al.: Eur. J. Neurol., 12, 96 (2005)
• Cawello, W., et al.: Clin. Pharmacokinet., 46, 851 (2005)
• Poewe, W., et al.: Lancet Neurol., 6, 513 (2005)