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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 22:45:27 UTC
Update Date2020-02-26 21:26:14 UTC
HMDB IDHMDB0006095
Secondary Accession Numbers
  • HMDB06095
Metabolite Identification
Common Name3-Methylsulfinylpropyl isothiocyanate
DescriptionConsumption of broccoli sprouts has shown to be effective at inhibiting Helicobacter pylori growth with sulforaphane being at least one of the active agents. Sulforaphane is an anticancer and antimicrobial compound which can be obtained by eating cruciferous vegetables such as brussel sprouts, broccoli, cauliflower, bok choy, kale, collards, arugula, broccoli sprouts, chinese broccoli, broccoli raab, kohlrabi, mustard, turnip, radish, watercress and cabbage. The enzyme myrosinase transforms glucoraphanin (a glucosinolate) into sulforaphane upon damage to the plant (such as from chewing). The young sprouts of broccoli and cauliflower are particularly rich in glucoraphanin.
Structure
Data?1582752373
Synonyms
ValueSource
3-Isothiocyanatopropyl methyl sulfoxideChEBI
IMSPChEBI
MethylsulfinylpropylisothiocyanateChEBI
3-Isothiocyanatopropyl methyl sulphoxideGenerator
Methylsulfinylpropylisothiocyanic acidGenerator
MethylsulphinylpropylisothiocyanateGenerator
Methylsulphinylpropylisothiocyanic acidGenerator
3-Methylsulfinylpropyl isothiocyanic acidGenerator
3-Methylsulphinylpropyl isothiocyanateGenerator
3-Methylsulphinylpropyl isothiocyanic acidGenerator
1-Isothiocyanato-3-(methylsulphinyl)propaneMeSH
1-Isothiocyanato-3-(methylsulfinyl)propaneMeSH
(R)-1-Isothiocyanato-3-(methylsulphinyl)propaneGenerator
Chemical FormulaC5H9NOS2
Average Molecular Weight163.261
Monoisotopic Molecular Weight163.012555295
IUPAC Name1-isothiocyanato-3-methanesulfinylpropane
Traditional Nameiberin
CAS Registry Number505-44-2
SMILES
CS(=O)CCCN=C=S
InChI Identifier
InChI=1S/C5H9NOS2/c1-9(7)4-2-3-6-5-8/h2-4H2,1H3
InChI KeyLELAOEBVZLPXAZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassSulfoxides
Sub ClassNot Available
Direct ParentSulfoxides
Alternative Parents
Substituents
  • Sulfoxide
  • Isothiocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfinyl compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
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
Water Solubility2.87 g/LALOGPS
logP0.69ALOGPS
logP-0.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.92 m³·mol⁻¹ChemAxon
Polarizability17.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.64631661259
DarkChem[M-H]-128.77531661259
DeepCCS[M+H]+130.44830932474
DeepCCS[M-H]-128.29730932474
DeepCCS[M-2H]-163.97330932474
DeepCCS[M+Na]+138.63630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methylsulfinylpropyl isothiocyanateCS(=O)CCCN=C=S2221.5Standard polar33892256
3-Methylsulfinylpropyl isothiocyanateCS(=O)CCCN=C=S1450.3Standard non polar33892256
3-Methylsulfinylpropyl isothiocyanateCS(=O)CCCN=C=S1417.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0mdi-9100000000-cba8365c48cdd07cae162017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 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 - 3-Methylsulfinylpropyl isothiocyanate 10V, Positive-QTOFsplash10-03di-1900000000-0f45d378074d3cee9fb12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 20V, Positive-QTOFsplash10-0bt9-5900000000-5c92d4441150139484052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 40V, Positive-QTOFsplash10-0006-9000000000-ad018f5caa95c24942fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 10V, Negative-QTOFsplash10-03di-9400000000-3156b9c5eaa02f6c4c702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 20V, Negative-QTOFsplash10-03di-9000000000-cbc7ae5d57c39a5f66be2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 40V, Negative-QTOFsplash10-08fr-9000000000-1a81c645e78474f5e1e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 10V, Negative-QTOFsplash10-03di-6900000000-67dd71397391c18484402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 20V, Negative-QTOFsplash10-03di-9300000000-229345e9b4ce8990cbaf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 40V, Negative-QTOFsplash10-0a4i-9000000000-dbe2377aeefa575913e52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 10V, Positive-QTOFsplash10-0udi-4900000000-40d813da252f99b6c9882021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 20V, Positive-QTOFsplash10-0zfr-9700000000-35cceb22e4f361385ddd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 40V, Positive-QTOFsplash10-05fr-9000000000-915fc15db1ff11b2de642021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.09 +/- 0.08 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008196
KNApSAcK IDC00047246
Chemspider ID10023
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10455
PDB IDNot Available
ChEBI ID89494
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 ReferencesNot Available