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Record Information
Version3.6
Creation Date2013-07-09 16:12:28 UTC
Update Date2017-08-18 12:55:45 UTC
HMDB IDHMDB0061012
Secondary Accession Numbers
  • HMDB61012
Metabolite Identification
Common Name(2S,3R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine
Description(2S,3R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine is a metabolite of aprepitant. Aprepitant (Emend) is an antiemetic chemical compound that belongs to a class of drugs called substance P antagonists (SPA). It mediates its effect by blocking the neurokinin 1 (NK1) receptor. Aprepitant is manufactured by Merck & Co. under the brand name Emend for prevention of acute and delayed chemotherapy-induced nausea and vomiting (CINV) and for prevention of postoperative nausea and vomiting. It was approved by the FDA in 2003. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H18F7NO2
Average Molecular Weight437.3512
Monoisotopic Molecular Weight437.12257626
IUPAC Name(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine
Traditional Name(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine
CAS Registry NumberNot Available
SMILES
C[C@@H](O[C@H]1OCCN[C@H]1C1=CC=C(F)C=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F
InChI Identifier
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
InChI KeyAFBDSAJOMZYQAI-CNOZUTPLSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassOxazinanes
Direct ParentPhenylmorpholines
Alternative Parents
Substituents
  • Phenylmorpholine
  • Trifluoromethylbenzene
  • Fluorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Acetal
  • Secondary aliphatic amine
  • Oxacycle
  • Azacycle
  • Secondary amine
  • Organohalogen compound
  • Alkyl halide
  • Hydrocarbon derivative
  • Alkyl fluoride
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.01 mg/mLALOGPS
logP4.11ALOGPS
logP5.69ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)6.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area30.49 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.03 m3·mol-1ChemAxon
Polarizability36.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00349
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0061012
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available