Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:00:17 UTC
Update Date2019-07-23 07:15:07 UTC
HMDB IDHMDB0060799
Secondary Accession Numbers
  • HMDB60799
Metabolite Identification
Common Name7-Hydroxyamoxapine
Description7-Hydroxyamoxapine belongs to the class of organic compounds known as dibenzoxazepines. Dibenzoxazepines are compounds containing a dibenzoxazepine moiety, which consists of two benzene connected by an oxazepine ring. 7-Hydroxyamoxapine is a very strong basic compound (based on its pKa). 7-Hydroxyamoxapine is a metabolite of amoxapine. Amoxapine (Amokisan, Asendin, Asendis, Defanyl, Demolox, Moxadil) is a tetracyclic antidepressant of the dibenzoxazepine family, though it is often classified as a secondary amine tricyclic antidepressant. It is the N-demethylated metabolite of Loxapine.
Structure
Data?1563866107
Synonyms
ValueSource
2-Chloro-11-(1-piperazinyl)dibenzo(b,F)(1,4)oxazepin-7-olMeSH
Chemical FormulaC17H16ClN3O2
Average Molecular Weight329.781
Monoisotopic Molecular Weight329.093104478
IUPAC Name13-chloro-10-(piperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-ol
Traditional Name7-hydroxyamoxapine
CAS Registry Number37081-76-8
SMILES
OC1=CC2=C(C=C1)N=C(N1CCNCC1)C1=C(O2)C=CC(Cl)=C1
InChI Identifier
InChI=1S/C17H16ClN3O2/c18-11-1-4-15-13(9-11)17(21-7-5-19-6-8-21)20-14-3-2-12(22)10-16(14)23-15/h1-4,9-10,19,22H,5-8H2
InChI KeyMEUGUMOVYNSGEW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzoxazepines. Dibenzoxazepines are compounds containing a dibenzoxazepine moiety, which consists of two benzene connected by an oxazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazepines
Sub ClassDibenzoxazepines
Direct ParentDibenzoxazepines
Alternative Parents
Substituents
  • Dibenzoxazepine
  • Diaryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aryl chloride
  • Aryl halide
  • 1,4-diazinane
  • Piperazine
  • Imidolactam
  • Benzenoid
  • Amidine
  • Carboxylic acid amidine
  • Secondary aliphatic amine
  • Oxacycle
  • Ether
  • Azacycle
  • Secondary amine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • 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 Solubility0.23 g/LALOGPS
logP2.67ALOGPS
logP1.93ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.25ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.09 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.8 m³·mol⁻¹ChemAxon
Polarizability33.76 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]+177.17430932474
DeepCCS[M-H]-174.81630932474
DeepCCS[M-2H]-208.61630932474
DeepCCS[M+Na]+183.85530932474
AllCCS[M+H]+174.632859911
AllCCS[M+H-H2O]+171.432859911
AllCCS[M+NH4]+177.532859911
AllCCS[M+Na]+178.332859911
AllCCS[M-H]-175.532859911
AllCCS[M+Na-2H]-174.832859911
AllCCS[M+HCOO]-174.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7-HydroxyamoxapineOC1=CC2=C(C=C1)N=C(N1CCNCC1)C1=C(O2)C=CC(Cl)=C14347.1Standard polar33892256
7-HydroxyamoxapineOC1=CC2=C(C=C1)N=C(N1CCNCC1)C1=C(O2)C=CC(Cl)=C12918.2Standard non polar33892256
7-HydroxyamoxapineOC1=CC2=C(C=C1)N=C(N1CCNCC1)C1=C(O2)C=CC(Cl)=C13078.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-Hydroxyamoxapine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2N=C(N3CCNCC3)C3=CC(Cl)=CC=C3OC2=C12995.9Semi standard non polar33892256
7-Hydroxyamoxapine,1TMS,isomer #2C[Si](C)(C)N1CCN(C2=NC3=CC=C(O)C=C3OC3=CC=C(Cl)C=C23)CC13119.5Semi standard non polar33892256
7-Hydroxyamoxapine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2N=C(N3CCN([Si](C)(C)C)CC3)C3=CC(Cl)=CC=C3OC2=C13090.9Semi standard non polar33892256
7-Hydroxyamoxapine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2N=C(N3CCN([Si](C)(C)C)CC3)C3=CC(Cl)=CC=C3OC2=C13007.2Standard non polar33892256
7-Hydroxyamoxapine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2N=C(N3CCN([Si](C)(C)C)CC3)C3=CC(Cl)=CC=C3OC2=C14288.7Standard polar33892256
7-Hydroxyamoxapine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2N=C(N3CCNCC3)C3=CC(Cl)=CC=C3OC2=C13185.6Semi standard non polar33892256
7-Hydroxyamoxapine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC=C(O)C=C3OC3=CC=C(Cl)C=C23)CC13358.2Semi standard non polar33892256
7-Hydroxyamoxapine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2N=C(N3CCN([Si](C)(C)C(C)(C)C)CC3)C3=CC(Cl)=CC=C3OC2=C13496.0Semi standard non polar33892256
7-Hydroxyamoxapine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2N=C(N3CCN([Si](C)(C)C(C)(C)C)CC3)C3=CC(Cl)=CC=C3OC2=C13409.8Standard non polar33892256
7-Hydroxyamoxapine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2N=C(N3CCN([Si](C)(C)C(C)(C)C)CC3)C3=CC(Cl)=CC=C3OC2=C14411.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7-Hydroxyamoxapine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9172000000-6434d9a2c64244c9beab2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Hydroxyamoxapine GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9016000000-7fe13b6c611595419c9d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Hydroxyamoxapine 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 - 7-Hydroxyamoxapine 10V, Positive-QTOFsplash10-001i-0009000000-ccb81a94432a74b5bbef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 20V, Positive-QTOFsplash10-001i-0039000000-c0958613e27f3e93d22b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 40V, Positive-QTOFsplash10-0cdr-4390000000-659a43e1fb3ef64d1fac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 10V, Negative-QTOFsplash10-004i-0019000000-3057f84f638347c801352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 20V, Negative-QTOFsplash10-004i-0049000000-051307c6dbe5f3e014e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 40V, Negative-QTOFsplash10-0006-9130000000-97f4c8f29fe8d3ffc9402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 10V, Positive-QTOFsplash10-001i-0009000000-2a0b3ee37f0986f8fe942021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 20V, Positive-QTOFsplash10-001i-0009000000-2a0b3ee37f0986f8fe942021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 40V, Positive-QTOFsplash10-0gb9-2193000000-9ea6bea84e27f0355c792021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 10V, Negative-QTOFsplash10-004i-0009000000-317a80daeb1f485525d02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 20V, Negative-QTOFsplash10-004i-1019000000-893efbf2efcb681e02052021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxyamoxapine 40V, Negative-QTOFsplash10-004i-3089000000-069bf530d0bc134fd7cf2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 Link7-Hydroxyamoxapine
METLIN IDNot Available
PubChem Compound162242
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