N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]-3-{[(2R,4S,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}propanamide

• ChemBase ID: 170209
• Molecular Formular: C27H36N2O7
• Molecular Mass: 500.58394
• Monoisotopic Mass: 500.2522515
• SMILES: C1CN(CCC1N(c1ccccc1)C(=O)CCO[C@@H]1OC([C@H]([C@@H](C1O)O)O)O)CCc1ccccc1
• Canonical SMILES: OC1O[C@@H](OCCC(=O)N(c2ccccc2)C2CCN(CC2)CCc2ccccc2)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H36N2O7/c30-22(14-18-35-27-25(33)23(31)24(32)26(34)36-27)29(20-9-5-2-6-10-20)21-12-16-28(17-13-21)15-11-19-7-3-1-4-8-19/h1-10,21,23-27,31-34H,11-18H2/t23-,24-,25?,26?,27+/m0/s1
• InChIKey: JEOGEDBYVNQFDA-HTLFAXABSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]-3-{[(2R,4S,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}propanamide
• IUPAC Traditional name: N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]-3-{[(2R,4S,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}propanamide
• Synonyms: 3-(β-D-Glucopyranuronosyloxy)-N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide; ω-Hydroxy Fentanyl O-β-D-Glucuronide

Database IDs

• PubChem SID: 164226119
• PubChem CID: 71748863

CALCULATED PROPERTIES

• Acid pKa: 11.222792
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.0381048
• LogD (pH = 7.4): -0.3526495
• Log P: 1.0300027
• Molar Refractivity: 132.7379 cm^3
• Polarizability: 52.6324 Å^3
• Polar Surface Area: 122.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H825330

ω-Hydroxy Fentanyl O-β-D-Glucuronide is the glucronide conjugate of ω-Hydroxy Fentanyl (H825300) and a potential metabolite of Fentanyl.