N-phenyl-N-(piperidin-4-yl)-3-{[(2R,4S,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}propanamide

• ChemBase ID: 171047
• Molecular Formular: C19H28N2O7
• Molecular Mass: 396.43482
• Monoisotopic Mass: 396.18965125
• SMILES: C1CNCCC1N(c1ccccc1)C(=O)CCO[C@@H]1OC([C@H]([C@@H](C1O)O)O)O
• Canonical SMILES: OC1O[C@@H](OCCC(=O)N(c2ccccc2)C2CCNCC2)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C19H28N2O7/c22-14(8-11-27-19-17(25)15(23)16(24)18(26)28-19)21(12-4-2-1-3-5-12)13-6-9-20-10-7-13/h1-5,13,15-20,23-26H,6-11H2/t15-,16-,17?,18?,19+/m0/s1
• InChIKey: ZFDAQLSGIUYALM-BAJPUEBJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-phenyl-N-(piperidin-4-yl)-3-{[(2R,4S,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}propanamide
• IUPAC Traditional name: N-phenyl-N-(piperidin-4-yl)-3-{[(2R,4S,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}propanamide
• Synonyms: 3-(β-D-Glucopyranuronosyloxy)-N-phenyl-N-4-piperidinylpropanamide; ω-Hydroxy Norfentanyl O-β-D-Glucuronide

Database IDs

• PubChem SID: 164226957
• PubChem CID: 71749237

CALCULATED PROPERTIES

• Acid pKa: 11.246016
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.586271
• LogD (pH = 7.4): -3.9003031
• Log P: -1.6220573
• Molar Refractivity: 98.0756 cm^3
• Polarizability: 39.507034 Å^3
• Polar Surface Area: 131.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948955

ω-Hydroxy Norfentanyl O-β-D-Glucuronide is the glucronide conjugate of ω-Hydroxy Norfentanyl (H948805) and a potential metabolite of Norfentanyl.