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Record Information
Version3.6
Creation Date2013-07-09 16:15:54 UTC
Update Date2016-02-11 08:17:48 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 KeyInChIKey=FNUZSRSXQFIOPL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Phenylpiperazine
  • Triazolopyridine
  • Substituted aniline
  • Dialkylarylamine
  • 2-chlorophenol
  • 2-halophenol
  • Aminophenol
  • N-alkylpiperazine
  • Pyridinone
  • Phenol
  • Halobenzene
  • Chlorobenzene
  • Aniline
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Triazole
  • Azole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • 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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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