(2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,14R,17S)-14,17-dihydroxy-4-methyl(13,14,15,15-2H4)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-10-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 171027
• Molecular Formular: C23H29NO10
• Molecular Mass: 479.47706
• Monoisotopic Mass: 479.17914613
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@@H](CC4)O)O2)CCN1C)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)Oc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@]4(O)CC[C@H]1O)C
• InChI: InChI=1S/C23H29NO10/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/h2-3,10,12,14-16,18-19,21,25-28,31H,4-8H2,1H3,(H,29,30)/t10-,12-,14+,15+,16-,18+,19?,21-,22+,23-/m1/s1
• InChIKey: IJMSQWNXMRYVBK-ZDLGVZNDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,14R,17S)-14,17-dihydroxy-4-methyl(13,14,15,15-^2H₄)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,14R,17S)-14,17-dihydroxy-4-methyl(13,14,15,15-^2H₄)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 6β-Hydroxy Oxymorphone-d4 β-D-Glucuronide

Database IDs

• PubChem SID: 164226937
• PubChem CID: 71749228

CALCULATED PROPERTIES

• Acid pKa: 2.6639864
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -4.201557
• LogD (pH = 7.4): -4.212203
• Log P: -4.201511
• Molar Refractivity: 112.4687 cm^3
• Polarizability: 45.27582 Å^3
• Polar Surface Area: 169.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H948887

A labelled metabolite of Oxymorphone.

REFERENCES

• Christensen, C.B., et al.: Pharmacol. Toxicol., 60, 75 (1987)
• Osborne, R., et al.: Clin. Pharmacol. Ther., 47, 12 (1987)
• Carrupt, P.A., et al.: J. Med. Chem., 34, 1272 (1987)