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Record Information
Version4.0
Creation Date2007-04-12 22:45:27 UTC
Update Date2017-09-27 08:24:41 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
Thumb
Synonyms
ValueSource
1-isothiocyanato-3-(Methylsulfinyl)propaneHMDB
3-Isothiocyanatopropyl methyl sulfoxideHMDB
MethylsulfinylpropylisothiocyanateHMDB
1-isothiocyanato-3-(Methylsulphinyl)propaneMeSH
IMSPMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as sulfoxides. These are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganosulfur compounds
Sub ClassSulfoxides
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:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0mdi-9100000000-cba8365c48cdd07cae16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-0f45d378074d3cee9fb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-5900000000-5c92d444115013948405View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ad018f5caa95c24942feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9400000000-3156b9c5eaa02f6c4c70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-cbc7ae5d57c39a5f66beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-9000000000-1a81c645e78474f5e1e0View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023829
KNApSAcK IDNot Available
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available