(2S,3S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-hydroxy-4-(2H3)methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 174811
• Molecular Formular: C23H27NO9
• Molecular Mass: 461.46178
• Monoisotopic Mass: 461.16858145
• 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)O
• Canonical SMILES: OC1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O
• InChI: InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-5-13(31-22-17(28)15(26)16(27)19(33-22)21(29)30)20(23)32-18-12(25)4-2-9(14(18)23)8-11(10)24/h2-5,10-11,13,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,13-,15?,16-,17+,19-,20-,22+,23-/m0/s1
• InChIKey: GNJCUHZOSOYIEC-MGAOPTOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-hydroxy-4-(^2H₃)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}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-hydroxy-4-(^2H₃)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}oxane-2-carboxylic acid
• Synonyms: Morphine-d3 6-β-D-Glucuronide; (5α,6α)-7,8-Didehydro-4,5-epoxy-3-hydroxy-17-methyl-d3-morphinan-6-yl β-D-Glucopyranosiduronic Acid; Morphine-d3 6-O-Glucuronide; Morphine-d3 6-Glucuronide; Morphine-d3 Glucuronide

Database IDs

• CAS Number: 219533-69-4
• PubChem SID: 164230721
• PubChem CID: 71750840

CALCULATED PROPERTIES

• Acid pKa: 2.874723
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -2.9851973
• LogD (pH = 7.4): -2.9913528
• Log P: -2.9848087
• Molar Refractivity: 112.4031 cm^3
• Polarizability: 44.346565 Å^3
• Polar Surface Area: 149.15 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: >230°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - M652312

Major labelled metabolite of Morphine that is a potent opioid receptor agonist. Analgesic (narcotic).Controlled substance.

REFERENCES

• Frances, B., et al.: J. Pharmacol. Exp. Ther, 262, 25 (1992)
• Wu, D., et al.: Drug Metab. Dispos., 25, 768 (1992)
• Krzanowska, E.K., et al.: Brain Res., 799, 329 (1992)