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Record Information
Version3.6
Creation Date2013-07-09 16:15:54 UTC
Update Date2017-03-02 22:05:42 UTC
HMDB IDHMDB61060
Secondary Accession NumbersNone
Metabolite Identification
Common Name4'-hydroxytrazodone
Description4'-hydroxytrazodone is a metabolite of trazodone. Trazodone (also sold under the brand names Desyrel, Oleptro, Beneficat, Deprax, Desirel, Molipaxin, Thombran, Trazorel, Trialodine, Trittico, and Mesyrel) is an antidepressant of the serotonin antagonist and reuptake inhibitor (SARI) class. It is a phenylpiperazine compound. Trazodone also has anxiolytic and hypnotic effects. Trazodone has considerably fewer prominent anticholinergic and sexual side effects than most of the tricyclic antidepressants (TCAs). (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H22ClN5O2
Average Molecular Weight387.863
Monoisotopic Molecular Weight387.14620268
IUPAC Name2-{3-[4-(3-chloro-4-hydroxyphenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one
Traditional Name2-{3-[4-(3-chloro-4-hydroxyphenyl)piperazin-1-yl]propyl}-[1,2,4]triazolo[4,3-a]pyridin-3-one
CAS Registry NumberNot Available
SMILES
OC1=C(Cl)C=C(C=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1
InChI Identifier
InChI=1S/C19H22ClN5O2/c20-16-14-15(5-6-17(16)26)23-12-10-22(11-13-23)7-3-9-25-19(27)24-8-2-1-4-18(24)21-25/h1-2,4-6,8,14,26H,3,7,9-13H2
InChI KeyFNUZSRSXQFIOPL-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
  • N-arylpiperazine
  • Phenylpiperazine
  • Aryl 1,2,4-triazol-3-one
  • Triazolopyridine
  • Aminophenol
  • P-aminophenol
  • 2-halophenol
  • Dialkylarylamine
  • Aniline or substituted anilines
  • Tertiary aliphatic/aromatic amine
  • 2-chlorophenol
  • Chlorobenzene
  • Halobenzene
  • Pyridinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • N-alkylpiperazine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Azole
  • 1,2,4-triazole
  • Triazole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organohalogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.43 mg/mLALOGPS
logP2.62ALOGPS
logP2.71ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)8.76ChemAxon
pKa (Strongest Basic)7.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area62.62 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity107.86 m3·mol-1ChemAxon
Polarizability41.24 Å3ChemAxon
Number of Rings4ChemAxon
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 IDDBMET00405
      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 LinkHMDB61060
      Metagene LinkHMDB61060
      METLIN IDNot Available
      PubChem Compound46781917
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available