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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:09:11 UTC
Update Date2019-07-23 07:15:27 UTC
HMDB IDHMDB0060952
Secondary Accession Numbers
  • HMDB60952
Metabolite Identification
Common Name2-hydroxyimipramine
Description2-hydroxyimipramine is a metabolite of imipramine. Imipramine (sold as Antideprin, Deprimin, Deprinol, Depsol, Depsonil, Dynaprin, Eupramin, Imipramil, Irmin, Janimine, Melipramin, Surplix, Tofranil), also known as melipramine, is an antidepressant medication, a tricyclic antidepressant of the dibenzazepine group. Imipramine is mainly used in the treatment of major depression and enuresis (inability to control urination). It has also been evaluated for use in panic disorder. (Wikipedia)
Structure
Data?1563866127
Synonyms
ValueSource
2-Hydroxyimipramine hydrochlorideHMDB
Chemical FormulaC19H24N2O
Average Molecular Weight296.4067
Monoisotopic Molecular Weight296.1888634
IUPAC Name2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol
Traditional Name2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol
CAS Registry NumberNot Available
SMILES
CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12
InChI Identifier
InChI=1S/C19H24N2O/c1-20(2)12-5-13-21-18-7-4-3-6-15(18)8-9-16-14-17(22)10-11-19(16)21/h3-4,6-7,10-11,14,22H,5,8-9,12-13H2,1-2H3
InChI KeyROTCPJFWLNDKHU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassDibenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Alkyldiarylamine
  • Tertiary aliphatic/aromatic amine
  • Azepine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Process

Naturally occurring process

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 Solubility0.23 g/LALOGPS
logP3.83ALOGPS
logP3.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)10.53ChemAxon
pKa (Strongest Basic)9.18ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.71 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.59 m³·mol⁻¹ChemAxon
Polarizability34.41 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.89931661259
DarkChem[M-H]-171.31931661259
DeepCCS[M-2H]-196.33930932474
DeepCCS[M+Na]+171.90530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-hydroxyimipramineCN(C)CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C123695.8Standard polar33892256
2-hydroxyimipramineCN(C)CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C122510.7Standard non polar33892256
2-hydroxyimipramineCN(C)CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C122527.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-hydroxyimipramine,1TMS,isomer #1CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C)=CC=C212544.8Semi standard non polar33892256
2-hydroxyimipramine,1TBDMS,isomer #1CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C212758.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-hydroxyimipramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9170000000-c25c75c1eef21d5ff0902017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-hydroxyimipramine GC-MS (1 TMS) - 70eV, Positivesplash10-0pb9-9044000000-0e13bf1e84f3ab096d862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-hydroxyimipramine 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 - 2-hydroxyimipramine 10V, Positive-QTOFsplash10-0002-0090000000-8d8c8134a93148bda2322017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 20V, Positive-QTOFsplash10-0f72-6090000000-ef333add7ecb6afc412e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 40V, Positive-QTOFsplash10-007c-9220000000-a094728c7b1d6bd6e3242017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 10V, Negative-QTOFsplash10-0002-0090000000-cbcfaec215c09531c84f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 20V, Negative-QTOFsplash10-01ot-0090000000-68ffadf8b3d60843ff7b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 40V, Negative-QTOFsplash10-03di-3690000000-f0d1657cbf38e63ff3da2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 10V, Positive-QTOFsplash10-0002-4090000000-714070a2c74dfcceae902021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 20V, Positive-QTOFsplash10-000i-9020000000-3224f32928ea10f281da2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 40V, Positive-QTOFsplash10-0a4r-9010000000-9760421fa4aea109d3d12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 10V, Negative-QTOFsplash10-0002-0090000000-6097eef1edfc41faed9b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 20V, Negative-QTOFsplash10-03di-0090000000-507f20bdb92a02e9e0272021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyimipramine 40V, Negative-QTOFsplash10-0a4i-0590000000-5a0f85f636ea1c8c75ba2021-10-12Wishart 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 Compound108051
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