(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5S,13R,17S)-17-hydroxy-4-methyl-14-oxo-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-10-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 176144
• Molecular Formular: C23H27NO10
• Molecular Mass: 477.46118
• Monoisotopic Mass: 477.16349607
• SMILES: c1(c2c3c(cc1)C[C@H]1[C@]4([C@@]3([C@H](C(=O)CC4)O2)CCN1C)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)C)ccc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C23H27NO10/c1-24-7-6-22-13-9-2-3-11(32-21-16(28)14(26)15(27)18(34-21)20(29)30)17(13)33-19(22)10(25)4-5-23(22,31)12(24)8-9/h2-3,12,14-16,18-19,21,26-28,31H,4-8H2,1H3,(H,29,30)/t12-,14-,15-,16+,18-,19-,21+,22-,23+/m0/s1
• InChIKey: ILRLBQVIWURYLX-LIJSDRPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5S,13R,17S)-17-hydroxy-4-methyl-14-oxo-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-10-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5S,13R,17S)-17-hydroxy-4-methyl-14-oxo-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-10-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (5α)-4,5-Epoxy-14-hydroxy-17-methyl-6-oxomorphinan-3-yl β-D-Glucopyranosiduronic Acid; Oxymorphone 3-Glucuronide; Oxymorphone 3-β-D-Glucuronide

Database IDs

• CAS Number: 770735-01-8
• PubChem SID: 164232054
• PubChem CID: 71751422

CALCULATED PROPERTIES

• Acid pKa: 2.680174
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -3.7902522
• LogD (pH = 7.4): -3.8431568
• Log P: -3.7909203
• Molar Refractivity: 111.5713 cm^3
• Polarizability: 44.812717 Å^3
• Polar Surface Area: 166.22 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O876810

A metabolite of Oxymorphone. Controlled substance (opiate). Analgesic (narcotic).

REFERENCES

• Eddy, N., et al.: J. Pharmacol. Exp. Ther., 125, 116 (1959)
• Cone, E., et al.: Drug Metab. Dispos., 11, 446 (1959)