(2S,3S,4S,5R,6R)-6-{[(1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 174917
• Molecular Formular: C27H35NO10
• Molecular Mass: 533.5675
• Monoisotopic Mass: 533.22609633
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@H](CC4)O[C@@H]3O[C@H]([C@H]([C@@H]([C@@H]3O)O)O)C(=O)O)O2)CCN1CC1CCC1)O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)O[C@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CCC2)ccc1O)O
• InChI: InChI=1S/C27H35NO10/c29-14-5-4-13-10-16-27(35)7-6-15(36-25-20(32)18(30)19(31)22(38-25)24(33)34)23-26(27,17(13)21(14)37-23)8-9-28(16)11-12-2-1-3-12/h4-5,12,15-16,18-20,22-23,25,29-32,35H,1-3,6-11H2,(H,33,34)/t15-,16+,18-,19-,20+,22-,23-,25+,26-,27+/m0/s1
• InChIKey: CATYADRMJMLDHO-SACJUFJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-10,17-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-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-10,17-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-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (5α,6α)-17-(Cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol 6-O-β-D-Glucuronide; Nalbuphine 6-O-β-D-Glucuronide

Database IDs

• PubChem SID: 164230827
• PubChem CID: 71750900

CALCULATED PROPERTIES

• Acid pKa: 2.8049595
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.4793804
• LogD (pH = 7.4): -2.4810438
• Log P: -2.4789493
• Molar Refractivity: 129.2806 cm^3
• Polarizability: 51.86025 Å^3
• Polar Surface Area: 169.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N232515

A metabolite of Nalbuphine (N232500).