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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:45:46 UTC
Update Date2021-10-13 07:13:16 UTC
HMDB IDHMDB0038445
Secondary Accession Numbers
  • HMDB38445
Metabolite Identification
Common Name1-Isothiocyanato-2-phenylethane
Description1-Isothiocyanato-2-phenylethane, also known as 2-phenylethyl isothiocyanate (PEITC) or (2-isothiocyanatoethyl) benzene is an isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties. It has a role as an antineoplastic agent, a metabolite and an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor. It belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. PEITC is found in high concentrations in kohlrabis. In terms of biosynthesis, PEITC is produced from gluconasturtiin by the action of the enzyme myrosinase. PEITC has been used in trials studying the prevention and treatment of leukemia, lung cancer, tobacco use disorder, and lymphoproliferative disorders.
Structure
Data?1563863198
Synonyms
ValueSource
(2-Isothiocyanatoethyl)benzeneChEBI
2-Phenylethyl isothiocyanateChEBI
beta-Phenethyl isothiocyanateChEBI
beta-Phenylethyl isothiocyanateChEBI
PEITCChEBI
Phenethyl mustard oilChEBI
PhenylaethylsenfoelChEBI
Phenylethyl isothiocyanateChEBI
2-Phenylethyl isothiocyanic acidGenerator
b-Phenethyl isothiocyanateGenerator
b-Phenethyl isothiocyanic acidGenerator
beta-Phenethyl isothiocyanic acidGenerator
Β-phenethyl isothiocyanateGenerator
Β-phenethyl isothiocyanic acidGenerator
b-Phenylethyl isothiocyanateGenerator
b-Phenylethyl isothiocyanic acidGenerator
beta-Phenylethyl isothiocyanic acidGenerator
Β-phenylethyl isothiocyanateGenerator
Β-phenylethyl isothiocyanic acidGenerator
Phenylethyl isothiocyanic acidGenerator
(2-Isothiocyanatoethyl)benzene, 9ciHMDB
Phenethyl isothiocyanateHMDB
PhenethylisothiocyanateHMDB
PEITC compoundHMDB
Phenethyl isothiocyanic acidHMDB
Chemical FormulaC9H9NS
Average Molecular Weight163.239
Monoisotopic Molecular Weight163.045569983
IUPAC Name(2-isothiocyanatoethyl)benzene
Traditional Namephenethyl isothiocyanate
CAS Registry Number2257-09-2
SMILES
S=C=NCCC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
InChI KeyIZJDOKYDEWTZSO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Isothiocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point139.00 to 140.00 °C. @ 11.00 mm HgThe Good Scents Company Information System
Water Solubility110 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP3.470The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP10(3.41) g/LALOGPS
logP10(3.08) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.7 m³·mol⁻¹ChemAxon
Polarizability18.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.73831661259
DarkChem[M-H]-131.00731661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Isothiocyanato-2-phenylethaneS=C=NCCC1=CC=CC=C12232.7Standard polar33892256
1-Isothiocyanato-2-phenylethaneS=C=NCCC1=CC=CC=C11424.0Standard non polar33892256
1-Isothiocyanato-2-phenylethaneS=C=NCCC1=CC=CC=C11464.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1-Isothiocyanato-2-phenylethane EI-B (Non-derivatized)splash10-0lxx-9600000000-1487c40cb717ac50d5402017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Isothiocyanato-2-phenylethane EI-B (Non-derivatized)splash10-0006-9300000000-dce10ef46bd36fa889952017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Isothiocyanato-2-phenylethane EI-B (Non-derivatized)splash10-0lxx-9600000000-1487c40cb717ac50d5402018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Isothiocyanato-2-phenylethane EI-B (Non-derivatized)splash10-0006-9300000000-dce10ef46bd36fa889952018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Isothiocyanato-2-phenylethane GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-8ba905c1a81fe91b0bff2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Isothiocyanato-2-phenylethane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Isothiocyanato-2-phenylethane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9400000000-89e2793dff2133a5d1962015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 10V, Positive-QTOFsplash10-03di-0900000000-eb29097e9abb6d0a69b62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 20V, Positive-QTOFsplash10-0a4i-1900000000-be2e5f6b10478c76d7a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 40V, Positive-QTOFsplash10-0a4i-8900000000-0665aea5aa041d7a38bc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 10V, Negative-QTOFsplash10-03di-2900000000-8cdabbdaddb353bffc802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 20V, Negative-QTOFsplash10-08fr-8900000000-ec5fdeb8c6a63b0341dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 40V, Negative-QTOFsplash10-0a4i-9100000000-eae0633f4737c22d4ec32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 10V, Positive-QTOFsplash10-0a4i-0900000000-d4c3b06d47f3ec6e00712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 20V, Positive-QTOFsplash10-0a4i-7900000000-e5f90967fb5289ac63ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 40V, Positive-QTOFsplash10-002f-9100000000-5c511cf6c615d97e03b32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 10V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 20V, Negative-QTOFsplash10-0a4i-9000000000-cd84ea46dbb46a75690a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanato-2-phenylethane 40V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12695
Phenol Explorer Compound IDNot Available
FooDB IDFDB004307
KNApSAcK IDC00057265
Chemspider ID15870
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenethyl_isothiocyanate
METLIN IDNot Available
PubChem Compound16741
PDB IDNot Available
ChEBI ID351346
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1049131
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .