(2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,17S)-4-(cyclopropylmethyl)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 174949
• Molecular Formular: C26H31NO10
• Molecular Mass: 517.52504
• Monoisotopic Mass: 517.1947962
• 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(=O)CC4)O2)CCN1CC1CC1)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@]4(O)CCC1=O)CC1CC1
• InChI: InChI=1S/C26H31NO10/c28-13-5-6-26(34)15-9-12-3-4-14(35-24-19(31)17(29)18(30)21(37-24)23(32)33)20-16(12)25(26,22(13)36-20)7-8-27(15)10-11-1-2-11/h3-4,11,15,17-19,21-22,24,29-31,34H,1-2,5-10H2,(H,32,33)/t15-,17+,18+,19-,21+,22+,24-,25+,26-/m1/s1
• InChIKey: KCSKQJYZSCIQRR-ODTDCTFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,17S)-4-(cyclopropylmethyl)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,17S)-4-(cyclopropylmethyl)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (5α)-17-(Cyclopropylmethyl)-4,5-epoxy-14-hydroxy-6-oxomorphinan-3-yl β-D-Glucopyranosiduronic Acid; Naltrexone 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 76630-71-2
• PubChem SID: 164230859
• PubChem CID: 71750923

CALCULATED PROPERTIES

• Acid pKa: 2.6801708
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -3.0096562
• LogD (pH = 7.4): -3.0203686
• Log P: -3.009599
• Molar Refractivity: 123.5133 cm^3
• Polarizability: 49.57085 Å^3
• Polar Surface Area: 166.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: >132°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - N285760

A metabolite of Naltrexone. Narcotic antagonist. Used in treatment of alcoholism.

REFERENCES

• Rodgers, R.M., et al.: Drug Metab. Dispos., 8, 390 (1980)
• Yaksh, T., et al.: J. Pharmacol. Exp. Ther., 244, 501 (1980)