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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:11:23 UTC
Update Date2019-07-23 07:14:44 UTC
HMDB IDHMDB0060630
Secondary Accession Numbers
  • HMDB60630
Metabolite Identification
Common Name(E)-2-hydroxydoxepin
Description(E)-2-hydroxydoxepin is a metabolite of doxepin. Doxepin is a psychotropic agent with tricyclic antidepressant and anxiolytic properties, known under many brand-names such as Aponal, the original preparation by Boehringer-Mannheim, now part of the Roche group; Adapine, Doxal, Deptran, Sinquan and Sinequan. As doxepin hydrochloride, it is the active ingredient in cream-based preparations (Zonalon and Xepin) for the treatment of dermatological itch. (Wikipedia)
Structure
Data?1563866084
SynonymsNot Available
Chemical FormulaC19H21NO2
Average Molecular Weight295.3755
Monoisotopic Molecular Weight295.157228921
IUPAC Name(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-5-ol
Traditional Name(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-5-ol
CAS Registry NumberNot Available
SMILES
CN(C)CC\C=C1/C2=CC(O)=CC=C2OCC2=C1C=CC=C2
InChI Identifier
InChI=1S/C19H21NO2/c1-20(2)11-5-8-17-16-7-4-3-6-14(16)13-22-19-10-9-15(21)12-18(17)19/h3-4,6-10,12,21H,5,11,13H2,1-2H3/b17-8-
InChI KeyGRQPGTWGEQWMMM-IUXPMGMMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxepines
Sub ClassDibenzoxepines
Direct ParentDibenzoxepines
Alternative Parents
Substituents
  • Dibenzoxepine
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Oxacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • 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 Solubility0.13 g/LALOGPS
logP3.84ALOGPS
logP2.94ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.07ChemAxon
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.7 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.23 m³·mol⁻¹ChemAxon
Polarizability33.67 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
DeepCCS[M+H]+171.39630932474
DeepCCS[M-H]-169.03830932474
DeepCCS[M-2H]-201.92430932474
DeepCCS[M+Na]+177.48930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(E)-2-hydroxydoxepinCN(C)CC\C=C1/C2=CC(O)=CC=C2OCC2=C1C=CC=C23655.0Standard polar33892256
(E)-2-hydroxydoxepinCN(C)CC\C=C1/C2=CC(O)=CC=C2OCC2=C1C=CC=C22350.3Standard non polar33892256
(E)-2-hydroxydoxepinCN(C)CC\C=C1/C2=CC(O)=CC=C2OCC2=C1C=CC=C22549.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(E)-2-hydroxydoxepin,1TMS,isomer #1CN(C)CC/C=C1/C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C)C=C122602.4Semi standard non polar33892256
(E)-2-hydroxydoxepin,1TBDMS,isomer #1CN(C)CC/C=C1/C2=CC=CC=C2COC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122850.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (E)-2-hydroxydoxepin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9040000000-44dc41d6196461d8e9df2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-2-hydroxydoxepin GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9013000000-1ada3fa3f839a5c6b22e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-2-hydroxydoxepin 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 - (E)-2-hydroxydoxepin 10V, Positive-QTOFsplash10-0002-0090000000-3c7af17ff121e45167eb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 20V, Positive-QTOFsplash10-0zgj-3190000000-f5340f8dd9219b60367c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 40V, Positive-QTOFsplash10-0pbc-9360000000-dbfa51b8e3061560faef2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 10V, Negative-QTOFsplash10-0006-0090000000-a29aa17b53d5064315412017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 20V, Negative-QTOFsplash10-0006-0090000000-e92584307aa000c1ec712017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 40V, Negative-QTOFsplash10-0a4i-3290000000-cdb65e536dc863ad82b62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 10V, Negative-QTOFsplash10-0006-0090000000-84f4977e0a47a94b8f5a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 20V, Negative-QTOFsplash10-0006-0090000000-61798c9bbfb2fd16459f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 40V, Negative-QTOFsplash10-0a4i-0190000000-c973eb09b911e494261c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 10V, Positive-QTOFsplash10-0002-0090000000-5739248b27ea332e1b0c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 20V, Positive-QTOFsplash10-0002-0090000000-c5116963f7b07395ca0a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-hydroxydoxepin 40V, Positive-QTOFsplash10-006x-3290000000-4a45e1b765238169aa262021-10-12Wishart 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 Compound67319009
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