(2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,17S)-14,17-dihydroxy-4-(prop-2-en-1-yl)-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: 174931
• Molecular Formular: C25H31NO10
• Molecular Mass: 505.51434
• Monoisotopic Mass: 505.1947962
• SMILES: [C@H]1(O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)Oc1c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(CC4)O)O2)CCN1CC=C)O
• Canonical SMILES: C=CCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(CC4)O)c(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C25H31NO10/c1-2-8-26-9-7-24-15-11-3-4-13(34-23-18(30)16(28)17(29)20(36-23)22(31)32)19(15)35-21(24)12(27)5-6-25(24,33)14(26)10-11/h2-4,12,14,16-18,20-21,23,27-30,33H,1,5-10H2,(H,31,32)/t12?,14-,16+,17+,18-,20+,21+,23-,24+,25-/m1/s1
• InChIKey: OZQAAEZUQYITNF-KSFFBVFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,17S)-14,17-dihydroxy-4-(prop-2-en-1-yl)-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,17S)-14,17-dihydroxy-4-(prop-2-en-1-yl)-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: (5α)-4,5-Epoxy-6,14-dihydroxy-17-(2-propenyl)morphinan-3-yl β-D-Glucopyranosiduronic Acid; Naloxol-3-glucuronide; Naloxol 3-β-D-Glucuronide

Database IDs

• CAS Number: 24326-39-4
• PubChem SID: 164230841
• PubChem CID: 71750913

CALCULATED PROPERTIES

• Acid pKa: 2.6639771
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -3.4703207
• LogD (pH = 7.4): -3.495784
• Log P: -3.4707074
• Molar Refractivity: 121.6314 cm^3
• Polarizability: 48.667408 Å^3
• Polar Surface Area: 169.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N284510

A metabolite of Naloxone (N285000). Narcotic antagonist.

REFERENCES

• Scheurer, U., et al.: J. Pharmacol. Exp. Ther., 252, 1324 (1990)
• Yuan, C., et al.: Clin. Pharmacol. Ther., 59, 469 (1990)
• Ulens, C., et al.: Biochem. Pharmacol., 62, 1273 (1990)
• Comert, M., et al.: Eur. J. Pharmacol., 511, 183 (1990)