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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 22:52:53 UTC
Update Date2021-09-26 23:17:45 UTC
HMDB IDHMDB0259914
Secondary Accession NumbersNone
Metabolite Identification
Common NameXaliproden
DescriptionXaliproden belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Based on a literature review a significant number of articles have been published on Xaliproden. This compound has been identified in human blood as reported by (PMID: 31557052 ). Xaliproden is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Xaliproden 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
1,2,3,6-Tetrahydro-1-(2-(2-naphthalenyl)ethyl)-4-(3-(trifluoromethyl)phenyl)-pyridineChEBI
1,2,3,6-Tetrahydro-1-(2-(2-naphthyl)ethyl)-4-(alpha,alpha,alpha-trifluoro-m-tolyl)pyridineChEBI
1,2,3,6-Tetrahydro-1-(2-(2-naphthyl)ethyl)-4-(a,a,a-trifluoro-m-tolyl)pyridineGenerator
1,2,3,6-Tetrahydro-1-(2-(2-naphthyl)ethyl)-4-(α,α,α-trifluoro-m-tolyl)pyridineGenerator
SR 57746ChEMBL
1-(2-(Naphth-2-yl)ethyl)-4-(3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridine hydrochlorideMeSH
1-(2-(Naphth-2-yl)ethyl)-4-(trifluoromethylphenyl)-1,2,5,6-tetrahydropyridine hydrochlorideMeSH
Xaliproden hydrochlorideMeSH
Chemical FormulaC24H22F3N
Average Molecular Weight381.442
Monoisotopic Molecular Weight381.170434201
IUPAC Name1-[2-(naphthalen-2-yl)ethyl]-4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine
Traditional Namexaliproden
CAS Registry NumberNot Available
SMILES
FC(F)(F)C1=CC(=CC=C1)C1=CCN(CCC2=CC3=CC=CC=C3C=C2)CC1
InChI Identifier
InChI=1S/C24H22F3N/c25-24(26,27)23-7-3-6-22(17-23)20-11-14-28(15-12-20)13-10-18-8-9-19-4-1-2-5-21(19)16-18/h1-9,11,16-17H,10,12-15H2
InChI KeyWJJYZXPHLSLMGE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Trifluoromethylbenzene
  • Phenethylamine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Hydropyridine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic nitrogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Amine
  • Hydrocarbon derivative
  • 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
logP6.26ALOGPS
logP6.23ChemAxon
logS-6.2ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.26 m³·mol⁻¹ChemAxon
Polarizability41.17 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+192.58832859911
AllCCS[M+H-H2O]+189.91132859911
AllCCS[M+Na]+195.76232859911
AllCCS[M+NH4]+195.05632859911
AllCCS[M-H]-187.46232859911
AllCCS[M+Na-2H]-186.32832859911
AllCCS[M+HCOO]-185.24432859911
DeepCCS[M+H]+190.1530932474
DeepCCS[M-H]-187.79230932474
DeepCCS[M-2H]-221.84530932474
DeepCCS[M+Na]+197.07330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XaliprodenFC(F)(F)C1=CC(=CC=C1)C1=CCN(CCC2=CC3=CC=CC=C3C=C2)CC13331.8Standard polar33892256
XaliprodenFC(F)(F)C1=CC(=CC=C1)C1=CCN(CCC2=CC3=CC=CC=C3C=C2)CC12673.1Standard non polar33892256
XaliprodenFC(F)(F)C1=CC(=CC=C1)C1=CCN(CCC2=CC3=CC=CC=C3C=C2)CC12812.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xaliproden GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0962000000-5ceccaa41d5ff2006d1c2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xaliproden 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 - Xaliproden 10V, Positive-QTOFsplash10-001i-0109000000-cfc295a33dfd7c25285b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xaliproden 20V, Positive-QTOFsplash10-0a5c-0897000000-f37f78e073a0d2babb292017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xaliproden 40V, Positive-QTOFsplash10-0a4i-0911000000-891b585e4ff1e1c3f1c62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xaliproden 10V, Negative-QTOFsplash10-001i-0009000000-1333266076e1b838b4dc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xaliproden 20V, Negative-QTOFsplash10-003r-0169000000-ae71d361402d168cade42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xaliproden 40V, Negative-QTOFsplash10-0kdi-2690000000-1419a73b0414be098ef02017-07-26Wishart 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 IDDB06393
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID114237
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkXaliproden
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID48520
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 ]