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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:11:24 UTC
Update Date2019-07-23 07:15:32 UTC
HMDB IDHMDB0060992
Secondary Accession Numbers
  • HMDB60992
Metabolite Identification
Common Name2-hydroxydesipramine
Description2-hydroxydesipramine is a metabolite of desipramine. Desipramine (also known as desmethylimipramine) is a tricyclic antidepressant (TCA). It inhibits the reuptake of norepinephrine and to a lesser extent serotonin. It is used to treat depression, but not considered a first line treatment since the introduction of SSRI antidepressants. Desipramine is an active metabolite of imipramine. It is sold under the brand names Norpramin and Pertofane. Along with other tricyclics, desipramine has found use in treating neuropathic pain. (Wikipedia)
Structure
Data?1563866132
Synonyms
ValueSource
2-Hydroxydesipramine monohydrochlorideHMDB
2-Hydroxydesipramine fumarateHMDB
2-Hydroxydesipramine monofumarateHMDB
2-OH-DMIHMDB
2-HydroxydesmethylimipramineHMDB
2-Hydroxy-desipramineHMDB
Chemical FormulaC18H22N2O
Average Molecular Weight282.3801
Monoisotopic Molecular Weight282.173213336
IUPAC Name2-[3-(methylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol
Traditional Name2-[3-(methylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol
CAS Registry NumberNot Available
SMILES
CNCCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12
InChI Identifier
InChI=1S/C18H22N2O/c1-19-11-4-12-20-17-6-3-2-5-14(17)7-8-15-13-16(21)9-10-18(15)20/h2-3,5-6,9-10,13,19,21H,4,7-8,11-12H2,1H3
InChI KeyNVJBOLMRGMDGLD-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
  • Secondary amine
  • Secondary aliphatic amine
  • Azacycle
  • Hydrocarbon derivative
  • Amine
  • 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

Source

Route of exposure

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 Solubility0.17 g/LALOGPS
logP10(3.34) g/LALOGPS
logP10(3.17) g/LChemAxon
logS10(-3.2) g/LALOGPS
pKa (Strongest Acidic)10.63ChemAxon
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area35.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity87.29 m³·mol⁻¹ChemAxon
Polarizability33.13 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]+166.1431661259
DarkChem[M-H]-166.16331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-hydroxydesipramineCNCCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C123761.7Standard polar33892256
2-hydroxydesipramineCNCCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C122533.9Standard non polar33892256
2-hydroxydesipramineCNCCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C122555.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-hydroxydesipramine,1TMS,isomer #1CNCCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C)=CC=C212533.8Semi standard non polar33892256
2-hydroxydesipramine,1TMS,isomer #2CN(CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C21)[Si](C)(C)C2785.4Semi standard non polar33892256
2-hydroxydesipramine,2TMS,isomer #1CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C)=CC=C21)[Si](C)(C)C2691.3Semi standard non polar33892256
2-hydroxydesipramine,2TMS,isomer #1CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C)=CC=C21)[Si](C)(C)C2795.7Standard non polar33892256
2-hydroxydesipramine,2TMS,isomer #1CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C)=CC=C21)[Si](C)(C)C3108.5Standard polar33892256
2-hydroxydesipramine,1TBDMS,isomer #1CNCCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C212743.7Semi standard non polar33892256
2-hydroxydesipramine,1TBDMS,isomer #2CN(CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C21)[Si](C)(C)C(C)(C)C3011.4Semi standard non polar33892256
2-hydroxydesipramine,2TBDMS,isomer #1CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21)[Si](C)(C)C(C)(C)C3120.3Semi standard non polar33892256
2-hydroxydesipramine,2TBDMS,isomer #1CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21)[Si](C)(C)C(C)(C)C3316.8Standard non polar33892256
2-hydroxydesipramine,2TBDMS,isomer #1CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21)[Si](C)(C)C(C)(C)C3301.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-hydroxydesipramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-5090000000-8e76a4f07afb1e4fce732017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-hydroxydesipramine GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9063000000-6e81780e6e12e98c39242017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-hydroxydesipramine 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-hydroxydesipramine 10V, Positive-QTOFsplash10-0f89-0090000000-bcb8aabdf8ebb58527c32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 20V, Positive-QTOFsplash10-0ul3-5090000000-40c13e82295f08b136db2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 40V, Positive-QTOFsplash10-006x-9230000000-6fcc2799f8061fa4efb02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 10V, Negative-QTOFsplash10-001i-0090000000-3409ea36098e6ee2dfed2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 20V, Negative-QTOFsplash10-01q9-0090000000-08b72e43d94db0d0a4332017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 40V, Negative-QTOFsplash10-03di-3690000000-7b5f4646b111996cb18b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 10V, Negative-QTOFsplash10-01q9-0090000000-c527909959df3c9546fd2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 20V, Negative-QTOFsplash10-01q9-0090000000-952acc2b1d05fbeb05352021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 40V, Negative-QTOFsplash10-0a4i-0090000000-0badbe995f9db9a9b99b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 10V, Positive-QTOFsplash10-00e9-9050000000-ed115f5372a00595c12d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 20V, Positive-QTOFsplash10-00di-9030000000-6fe4309013d9ef58dba82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxydesipramine 40V, Positive-QTOFsplash10-00dl-9010000000-25be336ae3f22a2180502021-09-25Wishart 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 Compound121249
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