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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:18:44 UTC
Update Date2021-09-26 22:55:15 UTC
HMDB IDHMDB0246282
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate
Description4-(2-{4-[3-(4-chlorophenyl)prop-2-en-1-yl]piperazin-1-yl}ethyl)benzoic acid belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Based on a literature review very few articles have been published on 4-(2-{4-[3-(4-chlorophenyl)prop-2-en-1-yl]piperazin-1-yl}ethyl)benzoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-(2-(1-(4-chlorocinnamyl)piperazin-4-yl)ethyl)benzoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate 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
4-(2-{4-[3-(4-chlorophenyl)prop-2-en-1-yl]piperazin-1-yl}ethyl)benzoateGenerator
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoic acidGenerator
Chemical FormulaC22H25ClN2O2
Average Molecular Weight384.9
Monoisotopic Molecular Weight384.1604558
IUPAC Name1-[2-(4-carboxyphenyl)ethyl]-4-[3-(4-chlorophenyl)prop-2-en-1-yl]piperazin-1-ium
Traditional Name1-[2-(4-carboxyphenyl)ethyl]-4-[3-(4-chlorophenyl)prop-2-en-1-yl]piperazin-1-ium
CAS Registry NumberNot Available
SMILES
[O-]C(=O)C1=CC=C(CC[NH+]2CCN(CC=CC3=CC=C(Cl)C=C3)CC2)C=C1
InChI Identifier
InChI=1S/C22H25ClN2O2/c23-21-9-5-18(6-10-21)2-1-12-24-14-16-25(17-15-24)13-11-19-3-7-20(8-4-19)22(26)27/h1-10H,11-17H2,(H,26,27)
InChI KeyYQIGCNRBMYEJID-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • Benzoic acid or derivatives
  • Benzoic acid
  • Styrene
  • Benzoyl
  • Halobenzene
  • N-alkylpiperazine
  • Chlorobenzene
  • Aralkylamine
  • 1,4-diazinane
  • Aryl chloride
  • Piperazine
  • Aryl halide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Amino acid
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP3.68ALOGPS
logP1.94ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)3.96ChemAxon
pKa (Strongest Basic)8.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.81 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity134.25 m³·mol⁻¹ChemAxon
Polarizability43.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+189.24530932474
DeepCCS[M-H]-186.88730932474
DeepCCS[M-2H]-220.82330932474
DeepCCS[M+Na]+196.05130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate[O-]C(=O)C1=CC=C(CC[NH+]2CCN(CC=CC3=CC=C(Cl)C=C3)CC2)C=C13259.1Standard non polar33892256
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate[O-]C(=O)C1=CC=C(CC[NH+]2CCN(CC=CC3=CC=C(Cl)C=C3)CC2)C=C13259.2Standard non polar33892256
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate[O-]C(=O)C1=CC=C(CC[NH+]2CCN(CC=CC3=CC=C(Cl)C=C3)CC2)C=C13455.4Semi standard non polar33892256
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate[O-]C(=O)C1=CC=C(CC[NH+]2CCN(CC=CC3=CC=C(Cl)C=C3)CC2)C=C13455.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate,1TMS,isomer #1C[Si](C)(C)[N+]1(CCC2=CC=C(C(=O)[O-])C=C2)CCN(CC=CC2=CC=C(Cl)C=C2)CC13407.4Semi standard non polar33892256
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate,1TMS,isomer #1C[Si](C)(C)[N+]1(CCC2=CC=C(C(=O)[O-])C=C2)CCN(CC=CC2=CC=C(Cl)C=C2)CC13342.2Standard non polar33892256
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate,1TMS,isomer #1C[Si](C)(C)[N+]1(CCC2=CC=C(C(=O)[O-])C=C2)CCN(CC=CC2=CC=C(Cl)C=C2)CC14297.8Standard polar33892256
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)[N+]1(CCC2=CC=C(C(=O)[O-])C=C2)CCN(CC=CC2=CC=C(Cl)C=C2)CC13637.3Semi standard non polar33892256
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)[N+]1(CCC2=CC=C(C(=O)[O-])C=C2)CCN(CC=CC2=CC=C(Cl)C=C2)CC13590.1Standard non polar33892256
4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)[N+]1(CCC2=CC=C(C(=O)[O-])C=C2)CCN(CC=CC2=CC=C(Cl)C=C2)CC14434.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-000w-0791000000-dc08f63cd5088d41a6352021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(2-(1-(4-Chlorocinnamyl)piperazin-4-yl)ethyl)benzoate 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 ID22906101
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound114892
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 ]