(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl](1,2-2H2)ethoxy]-3-(4-fluorophenyl)morpholine

• ChemBase ID: 162614
• Molecular Formular: C20H18F7NO2
• Molecular Mass: 437.3512424
• Monoisotopic Mass: 437.12257636
• SMILES: N1[C@H]([C@@H](O[C@@H](c2cc(cc(c2)C(F)(F)F)C(F)(F)F)C)OCC1)c1ccc(cc1)F
• Canonical SMILES: Fc1ccc(cc1)[C@@H]1NCCO[C@@H]1O[C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C
• InChI: InChI=1S/C20H18F7NO2/c1-11(13-8-14(19(22,23)24)10-15(9-13)20(25,26)27)30-18-17(28-6-7-29-18)12-2-4-16(21)5-3-12/h2-5,8-11,17-18,28H,6-7H2,1H3/t11-,17+,18-/m1/s1
• InChIKey: AFBDSAJOMZYQAI-CNOZUTPLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl](1,2-^2H₂)ethoxy]-3-(4-fluorophenyl)morpholine
• IUPAC Traditional name: (2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl](1,2-^2H₂)ethoxy]-3-(4-fluorophenyl)morpholine
• Synonyms: (2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl)ethoxy]-3-(4-fluorophenyl)morpholine-d2; 2-(R)-[1-(R)-(3,5-Bis(trifluoromethyl)phenyl)ethoxy]-3-(S)-fluorophenylmorpholine-d2[Aprepitant-M2-d2]

Database IDs

• PubChem SID: 162256749
• PubChem CID: 45038411

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.221725
• LogD (pH = 7.4): 5.5562763
• Log P: 5.6912107
• Molar Refractivity: 95.027 cm^3
• Polarizability: 35.301006 Å^3
• Polar Surface Area: 30.49 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Yellow Oil

DETAILS

Toronto Research Chemicals - B657152

A labelled metabolite of Aprepitant.

REFERENCES

• Ballard, T., et al.: Eur. J. Pharmacol., 412, 255 (2001)
• Campos, D., et al.: J. Clin. Oncol., 19, 1759 (2001)
• Severini, C., et al.: Pharmacol. Rev., 54, 285 (2002)