sodium (2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-14,17-dihydroxy-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-carboxylate

• ChemBase ID: 174944
• Molecular Formular: C26H32NNaO10
• Molecular Mass: 541.52275
• Monoisotopic Mass: 541.19239051
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@@H](CC4)O)O2)CCN1CC1CC1)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-].[Na+]
• 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)CC[C@H]1O)CC1CC1.[Na+]
• InChI: InChI=1S/C26H33NO10.Na/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;/h3-4,11,13,15,17-19,21-22,24,28-31,34H,1-2,5-10H2,(H,32,33);/q;+1/p-1/t13-,15-,17+,18+,19-,21+,22+,24-,25+,26-;/m1./s1
• InChIKey: OVHLXRIUXXIPRM-MPZMPHOMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-14,17-dihydroxy-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-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-14,17-dihydroxy-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-carboxylate
• Synonyms: (5α,6β)-17-(Cyclopropylmethyl)-4,5-epoxy-6,14-dihydroxy-morphinan-3-yl β-D-Glucopyranosiduronic Acid; 6β-Naltrexol 3-O-β-D-Glucuronide

Database IDs

• PubChem SID: 164230854
• PubChem CID: 71750919

CALCULATED PROPERTIES

• Acid pKa: 2.6639822
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -3.420972
• LogD (pH = 7.4): -3.4226851
• Log P: -3.4206746
• Molar Refractivity: 135.2478 cm^3
• Polarizability: 49.918995 Å^3
• Polar Surface Area: 172.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 199-203°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - N285710

A metabolite of 6β-Naltrexol (N285700). Narcotic antagonist.

REFERENCES

• Portoghese, P. et al,: J. Med. Chem., 37, 579 (1994)
• Ohkawa, S., et al.: J. Med. Chem., 41, 4177 (1994)