(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,17S)-17-hydroxy-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: 175703
• Molecular Formular: C22H25NO10
• Molecular Mass: 463.4346
• Monoisotopic Mass: 463.14784601
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=O)CC4)O2)CCN1)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2NCC3)ccc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C22H25NO10/c24-9-3-4-22(30)11-7-8-1-2-10(16-12(8)21(22,5-6-23-11)18(9)32-16)31-20-15(27)13(25)14(26)17(33-20)19(28)29/h1-2,11,13-15,17-18,20,23,25-27,30H,3-7H2,(H,28,29)/t11-,13+,14+,15-,17+,18+,20-,21+,22-/m1/s1
• InChIKey: GUMRUCMZEVRHNB-WFGUJTTASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,17S)-17-hydroxy-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,5R,13R,17S)-17-hydroxy-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-6-oxomorphinan-3-yl β-D-Glucopyranosiduronic Acid; Noroxymorphone Glucuronide; Noroxymorphone β-D-Glucuronide

Database IDs

• CAS Number: 76636-08-3
• PubChem SID: 164231613
• PubChem CID: 29986007

CALCULATED PROPERTIES

• Acid pKa: 2.6802628
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -3.9139264
• LogD (pH = 7.4): -3.9166696
• Log P: -3.9136443
• Molar Refractivity: 106.2766 cm^3
• Polarizability: 42.994255 Å^3
• Polar Surface Area: 175.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N825310

The main metabolite of Naltrexone in bile.

REFERENCES

• Rodgers, R. M., et al.: Drug Metab. Dispos., 8, 390 (1980)