(R)-1-Isothiocyanato-3-(methylsulfinyl)propane (CHEM026554)

Record Information
Version1.0
Creation Date2016-05-25 23:04:15 UTC
Update Date2026-08-23 03:01:58 UTC
Accession NumberCHEM026554
Identification
Common Name(R)-1-Isothiocyanato-3-(methylsulfinyl)propane
ClassSmall Molecule
Description
An isothiocyanate that is 1-isothiocyanatopropane in which a hydrogen at position 3 has been replaced by a methylsulfinyl group. A glucosinolate hydrolysis product found in many members of the Brassicaceae family, it is a quorum-sensing inhibitor (QSI) of the bacterial pathogen Pseudomonas aeruginosa.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
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 Mass163.261 g/mol
Monoisotopic Mass163.013 g/mol
CAS Registry Number37791-20-1
IUPAC Name1-isothiocyanato-3-methanesulfinylpropane
Traditional Nameiberin
SMILESCS(=O)CCCN=C=S
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0006095
FooDB IDFDB008196
Phenol Explorer IDNot Available
KNApSAcK IDC00047246
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10023
ChEBI ID89494
PubChem Compound ID10455
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15740016
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16289008
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16931178
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17167713
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17273780
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17310076
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19489030
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22286987
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23403058
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25155599
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26679410
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=8225130
13.