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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 22:49:33 UTC
Update Date2022-11-23 22:29:21 UTC
HMDB IDHMDB0259875
Secondary Accession NumbersNone
Metabolite Identification
Common NameVortioxetine
Description1-{2-[(2,4-dimethylphenyl)sulfanyl]phenyl}piperazine, also known as brintellix, belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. Based on a literature review a small amount of articles have been published on 1-{2-[(2,4-dimethylphenyl)sulfanyl]phenyl}piperazine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Vortioxetine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Vortioxetine 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
BrintellixKegg
1-{2-[(2,4-dimethylphenyl)sulphanyl]phenyl}piperazineGenerator
1-(2-(2,4-Dimethylphenylsulfanyl)phenyl)piperazineMeSH
Vortioxetine hydrobromideMeSH
Chemical FormulaC18H22N2S
Average Molecular Weight298.45
Monoisotopic Molecular Weight298.15036989
IUPAC Name1-{2-[(2,4-dimethylphenyl)sulfanyl]phenyl}piperazine
Traditional Namevortioxetine
CAS Registry NumberNot Available
SMILES
CC1=CC(C)=C(SC2=CC=CC=C2N2CCNCC2)C=C1
InChI Identifier
InChI=1S/C18H22N2S/c1-14-7-8-17(15(2)13-14)21-18-6-4-3-5-16(18)20-11-9-19-10-12-20/h3-8,13,19H,9-12H2,1-2H3
InChI KeyYQNWZWMKLDQSAC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • Phenylpiperazine
  • N-arylpiperazine
  • Diarylthioether
  • Aryl thioether
  • M-xylene
  • Xylene
  • Tertiary aliphatic/aromatic amine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Thiophenol ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary amine
  • Secondary aliphatic amine
  • Secondary amine
  • Azacycle
  • Thioether
  • Sulfenyl compound
  • Organopnictogen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP4.51ALOGPS
logP4.76ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)8.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.27 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.01 m³·mol⁻¹ChemAxon
Polarizability34.58 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]+170.36732859911
AllCCS[M+H-H2O]+166.98532859911
AllCCS[M+Na]+174.40432859911
AllCCS[M+NH4]+173.50332859911
AllCCS[M-H]-174.30632859911
AllCCS[M+Na-2H]-173.69232859911
AllCCS[M+HCOO]-173.14532859911
DeepCCS[M+H]+168.88330932474
DeepCCS[M-H]-166.52530932474
DeepCCS[M-2H]-199.41130932474
DeepCCS[M+Na]+174.97730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VORTIOXETINECC1=CC(C)=C(SC2=CC=CC=C2N2CCNCC2)C=C13212.6Standard polar33892256
VORTIOXETINECC1=CC(C)=C(SC2=CC=CC=C2N2CCNCC2)C=C12403.1Standard non polar33892256
VORTIOXETINECC1=CC(C)=C(SC2=CC=CC=C2N2CCNCC2)C=C12555.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
VORTIOXETINE,1TMS,isomer #1CC1=CC=C(SC2=CC=CC=C2N2CCN([Si](C)(C)C)CC2)C(C)=C12726.1Semi standard non polar33892256
VORTIOXETINE,1TMS,isomer #1CC1=CC=C(SC2=CC=CC=C2N2CCN([Si](C)(C)C)CC2)C(C)=C12573.2Standard non polar33892256
VORTIOXETINE,1TMS,isomer #1CC1=CC=C(SC2=CC=CC=C2N2CCN([Si](C)(C)C)CC2)C(C)=C13262.6Standard polar33892256
VORTIOXETINE,1TBDMS,isomer #1CC1=CC=C(SC2=CC=CC=C2N2CCN([Si](C)(C)C(C)(C)C)CC2)C(C)=C12946.1Semi standard non polar33892256
VORTIOXETINE,1TBDMS,isomer #1CC1=CC=C(SC2=CC=CC=C2N2CCN([Si](C)(C)C(C)(C)C)CC2)C(C)=C12763.4Standard non polar33892256
VORTIOXETINE,1TBDMS,isomer #1CC1=CC=C(SC2=CC=CC=C2N2CCN([Si](C)(C)C(C)(C)C)CC2)C(C)=C13398.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vortioxetine GC-MS (Non-derivatized) - 70eV, Positivesplash10-052o-1980000000-f946530f9325fe92b2f12021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vortioxetine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8141643
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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 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 ]