(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxane-2-carboxylic acid; 3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-4,5-dihydro-1H-1,2,4-triazol-5-one

• ChemBase ID: 160772
• Molecular Formular: C30H33F7N4O9
• Molecular Mass: 726.5932424
• Monoisotopic Mass: 726.2135762
• SMILES: n1[nH]c(=O)[nH]c1CN1[C@H]([C@@H](O[C@@H](c2cc(cc(c2)C(F)(F)F)C(F)(F)F)C)OCC1)c1ccc(cc1)F.[C@H]1(O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C
• Canonical SMILES: C[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O.Fc1ccc(cc1)[C@H]1[C@H](OCCN1Cc1n[nH]c(=O)[nH]1)O[C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C
• InChI: InChI=1S/C23H21F7N4O3.C7H12O6/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)37-20-19(13-2-4-17(24)5-3-13)34(6-7-36-20)11-18-31-21(35)33-32-18;1-2-3(8)4(9)5(10)6(13-2)7(11)12/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H2,31,32,33,35);2-6,8-10H,1H3,(H,11,12)/t12-,19+,20-;2-,3-,4+,5-,6-/m10/s1
• InChIKey: KDUZYRPKZDEBSB-ZQGGTROGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxane-2-carboxylic acid; 3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: (2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxane-2-carboxylic acid; aprepitant
• Synonyms: 5-[[(2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one Glucuronide Sodium Salt; Aprepitant β-Glucuronide Sodium Salt

Database IDs

• PubChem SID: 162254907
• PubChem CID: 71313475

CALCULATED PROPERTIES

• Acid pKa: 9.646593
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.211254
• LogD (pH = 7.4): 5.2134037
• Log P: 5.215729
• Molar Refractivity: 116.9282 cm^3
• Polarizability: 43.315456 Å^3
• Polar Surface Area: 75.19 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A729810

A metabolite of Aprepitant (A729800).

REFERENCES

• Dean, B., et al.: Drug Metab. Rev., 32, 261 (2000)