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

• ChemBase ID: 174808
• 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)O2)CCN1C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=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@@H]4C=C[C@@H]1O)C
• InChI: InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-4-12(25)20(23)32-18-13(5-2-9(14(18)23)8-11(10)24)31-22-17(28)15(26)16(27)19(33-22)21(29)30/h2-5,10-12,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11-,12-,15-,16-,17+,19-,20-,22+,23-/m0/s1
• InChIKey: WAEXKFONHRHFBZ-MYIQFFIVSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 164230718
• PubChem CID: 71750837

CALCULATED PROPERTIES

• Acid pKa: 2.673982
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.4821389
• LogD (pH = 7.4): -3.4876406
• Log P: -3.4819388
• Molar Refractivity: 112.1342 cm^3
• Polarizability: 44.344105 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: 234-238°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - M652302

A labelled metabolite of Morphine. Analog of Morphine as molecular chameleon with unexpected lipophilicity.Controlled substance.

REFERENCES

• Christensen, C.B., et al.: Pharmacol. Toxicol., 60, 75 (1987)
• Coughtrie, M.W., et al.: Biochem. Pharmacol., 38, 3273 (1987)