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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:15:54 UTC
Update Date2019-07-23 07:15:41 UTC
HMDB IDHMDB0061060
Secondary Accession Numbers
  • HMDB61060
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
Data?1563866141
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
Description Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines 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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.43 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity107.86 m³·mol⁻¹ChemAxon
Polarizability41.24 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+186.65930932474
DeepCCS[M-H]-184.30130932474
DeepCCS[M-2H]-218.46930932474
DeepCCS[M+Na]+193.82130932474
AllCCS[M+H]+188.732859911
AllCCS[M+H-H2O]+186.132859911
AllCCS[M+NH4]+191.132859911
AllCCS[M+Na]+191.832859911
AllCCS[M-H]-189.032859911
AllCCS[M+Na-2H]-188.732859911
AllCCS[M+HCOO]-188.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4'-hydroxytrazodoneOC1=C(Cl)C=C(C=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC14166.9Standard polar33892256
4'-hydroxytrazodoneOC1=C(Cl)C=C(C=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC13332.3Standard non polar33892256
4'-hydroxytrazodoneOC1=C(Cl)C=C(C=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC13706.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4'-hydroxytrazodone,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(N2CCN(CCCN3N=C4C=CC=CN4C3=O)CC2)C=C1Cl3451.8Semi standard non polar33892256
4'-hydroxytrazodone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(N2CCN(CCCN3N=C4C=CC=CN4C3=O)CC2)C=C1Cl3708.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4'-hydroxytrazodone GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-1960000000-1eb48f83823476f0dc662017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4'-hydroxytrazodone GC-MS (1 TMS) - 70eV, Positivesplash10-006w-5793600000-5efb0d5b0690274952792017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4'-hydroxytrazodone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 10V, Positive-QTOFsplash10-000i-0309000000-933d43ea1f35220ce4802017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 20V, Positive-QTOFsplash10-002r-4956000000-e58afe7993ed297497162017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 40V, Positive-QTOFsplash10-052s-9830000000-8e30afd67ec6e8533cbc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 10V, Negative-QTOFsplash10-000i-1309000000-3e2732588a3c25b65fc32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 20V, Negative-QTOFsplash10-001i-9848000000-1fdfeacf44c5348ab0a92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 40V, Negative-QTOFsplash10-057i-9810000000-4897debedec8eed8ddda2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 10V, Positive-QTOFsplash10-000i-0009000000-b71c48caecbf1e59ab632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 20V, Positive-QTOFsplash10-000i-0129000000-6e15c293d6526dce3a422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 40V, Positive-QTOFsplash10-02vi-1791000000-687e33bf8b7b40d77cd22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 10V, Negative-QTOFsplash10-000i-1009000000-63105e22cc0ce22ad0d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 20V, Negative-QTOFsplash10-0019-3009000000-17b9083487dc67b45b6d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-hydroxytrazodone 40V, Negative-QTOFsplash10-001i-9542000000-e1f4e8023f3adc286a492021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound46781917
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available