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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:14:17 UTC
Update Date2017-10-23 19:15:51 UTC
HMDB IDHMDB0061040
Secondary Accession Numbers
  • HMDB61040
Metabolite Identification
Common Namehydroxynefazodone
Descriptionhydroxynefazodone is a metabolite of nefazodone. Nefazodone (Serzone, Nefadar) is an antidepressant marketed by Bristol-Myers Squibb. Its sale was discontinued in 2003 in some countries due to the rare incidence of hepatotoxicity (liver damage), which could lead to the need for a liver transplant, or even death. The incidence of severe liver damage is approximately 1 in every 250,000 to 300,000 patient-years. On June 14, 2004, Bristol-Myers Squibb discontinued the sale of Serzone in the United States and Canada. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H32ClN5O3
Average Molecular Weight486.006
Monoisotopic Molecular Weight485.219367622
IUPAC Name1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3-(1-hydroxyethyl)-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one
Traditional Name2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-5-(1-hydroxyethyl)-4-(2-phenoxyethyl)-1,2,4-triazol-3-one
CAS Registry NumberNot Available
SMILES
CC(O)C1=NN(CCCN2CCN(CC2)C2=CC=CC(Cl)=C2)C(=O)N1CCOC1=CC=CC=C1
InChI Identifier
InChI=1S/C25H32ClN5O3/c1-20(32)24-27-31(25(33)30(24)17-18-34-23-9-3-2-4-10-23)12-6-11-28-13-15-29(16-14-28)22-8-5-7-21(26)19-22/h2-5,7-10,19-20,32H,6,11-18H2,1H3
InChI KeyVKGQYGXMUUBRBD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDiazinanes
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • Phenylpiperazine
  • N-arylpiperazine
  • Phenol ether
  • Tertiary aliphatic/aromatic amine
  • Phenoxy compound
  • Dialkylarylamine
  • Aniline or substituted anilines
  • Chlorobenzene
  • N-alkylpiperazine
  • Halobenzene
  • Alkyl aryl ether
  • Aryl halide
  • Aryl chloride
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Azole
  • 1,2,4-triazole
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Ether
  • Organic nitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic alcohol
  • Organonitrogen compound
  • Amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility0.1 g/LALOGPS
logP3.13ALOGPS
logP3.7ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)14.01ChemAxon
pKa (Strongest Basic)7.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.85 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity133.95 m³·mol⁻¹ChemAxon
Polarizability52.73 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0cfu-6396500000-55b57e70f0f6b915a586View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9224560000-561d360936059220ee61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0041900000-9bed52369deef0adb8a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-1294200000-cc356241e9e3521df429View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-4892000000-8dfc154e51cb17776a4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-2941500000-2c85e764289f82ffd40cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-7931100000-1ce923e379701210c153View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-a0fea68b0ae2caa583e0View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00379
      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
      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