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

• ChemBase ID: 168686
• Molecular Formular: C25H31NO9
• Molecular Mass: 489.51494
• Monoisotopic Mass: 489.19988158
• SMILES: c1(c2c3c(cc1)C[C@H]1[C@H]4[C@@]3([C@H]([C@H](C=C4)O[C@@H]3O[C@H]([C@H](C([C@@H]3O)O)O)C(=O)O)O2)CCN1C)OCC
• Canonical SMILES: CCOc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@@H](C2)[C@@H]4C=C[C@@H]1O[C@@H]1O[C@@H](C(=O)O)[C@H](C([C@@H]1O)O)O)C
• InChI: InChI=1S/C25H31NO9/c1-3-32-14-6-4-11-10-13-12-5-7-15(22-25(12,8-9-26(13)2)16(11)20(14)34-22)33-24-19(29)17(27)18(28)21(35-24)23(30)31/h4-7,12-13,15,17-19,21-22,24,27-29H,3,8-10H2,1-2H3,(H,30,31)/t12-,13-,15-,17?,18-,19+,21-,22-,24+,25-/m0/s1
• InChIKey: YSMMNXFGGVDXFK-GFIBSHDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5R,6R)-6-{[(1S,5S,13R,14S,17R)-10-ethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,5R,6R)-6-{[(1S,5S,13R,14S,17R)-10-ethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (5α,6α)-7,8-Didehydro-4,5-epoxy-3-ethoxy-17-methylmorphinan-6-yl β-D-Glucopyranosiduronic Acid; Ethylmorphine 6-Glucuronide; Ethyl Morphine 6-β-D-Glucuronide

Database IDs

• CAS Number: 168074-32-6
• PubChem SID: 162262818
• PubChem CID: 71316640

CALCULATED PROPERTIES

• Acid pKa: 2.8704479
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -2.4824708
• LogD (pH = 7.4): -2.4874222
• Log P: -2.482054
• Molar Refractivity: 121.634 cm^3
• Polarizability: 48.06441 Å^3
• Polar Surface Area: 138.15 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E925160

A metabolite of Ethylmorphine in man. Controlled substance

REFERENCES

• Euler, M., et al.: Ther. Drug. Monit., 25, 645 (2003)
• Rivier, L., et al.: Anal. Chim. Acta, 492, 69 (2003)
• Edinboro, L., et al.: J. Anal. Toxicol., 29, 704 (2003)