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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 23:07:29 UTC
Update Date2021-09-26 23:17:58 UTC
HMDB IDHMDB0260049
Secondary Accession NumbersNone
Metabolite Identification
Common Namezotepine
DescriptionZotepine, also known as setous or lodopin, belongs to the class of organic compounds known as dibenzothiepins. Dibenzothiepins are compounds containing a dibenzothiepin moiety, which consists of two benzene connected by a thiepine ring. Based on a literature review a significant number of articles have been published on Zotepine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Zotepine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically zotepine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
2-Chlor-11-(2-dimethylaminoaethoxy)-dibenzo(b,F)-thiepinChEBI
2-Chloro-11-(2-(dimethylamino)ethoxy)dibenzo(b,F)thiepinChEBI
LodopinChEBI
SetousChEBI
ZotepinaChEBI
ZotepinumChEBI
ZoleptilMeSH
2-chloro-11-(2-Dimethylaminoethoxy)dibenzo(b,F)thiepineMeSH
NipoleptMeSH
Chemical FormulaC18H18ClNOS
Average Molecular Weight331.86
Monoisotopic Molecular Weight331.0797631
IUPAC Name[2-({6-chloro-2-thiatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-9-yl}oxy)ethyl]dimethylamine
Traditional Namecompound-4
CAS Registry NumberNot Available
SMILES
CN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C12
InChI Identifier
InChI=1S/C18H18ClNOS/c1-20(2)9-10-21-16-11-13-5-3-4-6-17(13)22-18-8-7-14(19)12-15(16)18/h3-8,11-12H,9-10H2,1-2H3
InChI KeyHDOZVRUNCMBHFH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzothiepins. Dibenzothiepins are compounds containing a dibenzothiepin moiety, which consists of two benzene connected by a thiepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiepins
Sub ClassDibenzothiepins
Direct ParentDibenzothiepins
Alternative Parents
Substituents
  • Dibenzothiepin
  • Diarylthioether
  • Aryl thioether
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP4.74ALOGPS
logP4.51ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.92ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.61 m³·mol⁻¹ChemAxon
Polarizability36.21 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
AllCCS[M+H]+174.53732859911
AllCCS[M+H-H2O]+171.26332859911
AllCCS[M+Na]+178.4432859911
AllCCS[M+NH4]+177.56932859911
AllCCS[M-H]-176.88332859911
AllCCS[M+Na-2H]-176.39932859911
AllCCS[M+HCOO]-176.00732859911
DeepCCS[M-2H]-202.70330932474
DeepCCS[M+Na]+178.26930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
zotepineCN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C123543.1Standard polar33892256
zotepineCN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C122511.5Standard non polar33892256
zotepineCN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C122573.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - zotepine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-80e02fa4b206648fd60e2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - zotepine 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 - zotepine 10V, Positive-QTOFsplash10-001i-1009000000-96045d6ac7460e729f342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - zotepine 20V, Positive-QTOFsplash10-00di-9124000000-514ffa2cfc3d46bf4d112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - zotepine 40V, Positive-QTOFsplash10-076r-9510000000-1a60fee5bb74f9f306c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - zotepine 10V, Negative-QTOFsplash10-001i-0039000000-3caf4f9bea17829913e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - zotepine 20V, Negative-QTOFsplash10-0a59-0095000000-c0ec1fc18f181403f5aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - zotepine 40V, Negative-QTOFsplash10-0a4i-1190000000-8eaef1c160ca62b1cb732016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09225
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5534
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkZotepine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID32316
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]