(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,17S)-17-hydroxy-14-oxo-4-[(2H5)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}oxane-2-carboxylic acid

• ChemBase ID: 174936
• Molecular Formular: C25H29NO10
• Molecular Mass: 503.49846
• Monoisotopic Mass: 503.17914613
• 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(=O)CC4)O2)CCN1CC=C)O
• Canonical SMILES: C=CCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C25H29NO10/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/h2-4,14,16-18,20-21,23,28-30,33H,1,5-10H2,(H,31,32)/t14-,16+,17+,18-,20+,21+,23-,24+,25-/m1/s1
• InChIKey: DSRNCSJRHACUJL-JXOQMJNJSA-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-4-[(^2H₅)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}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-4-[(^2H₅)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}oxane-2-carboxylic acid
• Synonyms: (5α)-4,5-Epoxy-14-hydroxy-6-oxo-17-(2-propenyl-d5)morphinan-3-yl β-D-Glucopyranosiduronic Acid; Naloxone-3-glucuronide-d5; Naloxone-d5 3-β-D-Glucuronide

Database IDs

• PubChem SID: 164230846
• PubChem CID: 71750916

CALCULATED PROPERTIES

• Acid pKa: 2.6801634
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -3.0590346
• LogD (pH = 7.4): -3.172641
• Log P: -3.0590029
• Molar Refractivity: 120.734 cm^3
• Polarizability: 48.20415 Å^3
• Polar Surface Area: 166.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N285012

A labelled 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)