(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-[(2S)-3-{[(1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl]oxy}-3-oxo-2-phenylpropoxy]oxane-2-carboxylic acid

• ChemBase ID: 177719
• Molecular Formular: C23H29NO10
• Molecular Mass: 479.47706
• Monoisotopic Mass: 479.17914613
• SMILES: O(C(=O)[C@@H](c1ccccc1)CO[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)[C@H]1C[C@H]2[C@H]3[C@@H]([C@H](N2C)C1)O3
• Canonical SMILES: O=C([C@@H](c1ccccc1)CO[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)O[C@@H]1C[C@@H]2[C@@H]3[C@H]([C@H](C1)N2C)O3
• InChI: InChI=1S/C23H29NO10/c1-24-13-7-11(8-14(24)19-18(13)33-19)32-22(30)12(10-5-3-2-4-6-10)9-31-23-17(27)15(25)16(26)20(34-23)21(28)29/h2-6,11-20,23,25-27H,7-9H2,1H3,(H,28,29)/t11-,12-,13-,14+,15-,16-,17+,18-,19+,20-,23+/m1/s1
• InChIKey: NIZFCRZRBBERQF-OYPVIPJJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-[(2S)-3-{[(1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl]oxy}-3-oxo-2-phenylpropoxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-[(2S)-3-{[(1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl]oxy}-3-oxo-2-phenylpropoxy]oxane-2-carboxylic acid
• Synonyms: (2S)-3-[[(1α,2β,4β,5α,7β)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl]oxy]-3-oxo-2-phenylpropyl β-D-Glucopyranosiduronic Acid; (-)-Scopolamine 9'-glucuronide; Scopolamine O-β-D-glucuronide; Scopolamine β-D-Glucuronide

Database IDs

• CAS Number: 17660-02-5
• PubChem SID: 164233629
• PubChem CID: 71752171

CALCULATED PROPERTIES

• Acid pKa: 2.9379823
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -3.2782018
• LogD (pH = 7.4): -3.690717
• Log P: -3.271706
• Molar Refractivity: 112.002 cm^3
• Polarizability: 45.69069 Å^3
• Polar Surface Area: 158.52 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 167-172°C (dec)

Safety Information

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

DETAILS

Toronto Research Chemicals - S200010

A metabolite of Scopolamine.

REFERENCES

• Shutt, L., et al.: Anaesthesia, 34, 476 (1979)
• Wada, S., et al.: Xenobiotica, 21, 1289 (1979)
• Chen, X., et al.: Acta Pharm. Sin., 33, 849(1979)