Sulforaphane (CHEM028336)

Record Information
Version1.0
Creation Date2016-05-26 00:23:15 UTC
Update Date2026-08-23 05:39:59 UTC
Accession NumberCHEM028336
Identification
Common NameSulforaphane
ClassSmall Molecule
Description
An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SulforafanChEBI
SulphorafanGenerator
SulphoraphaneGenerator
(R)-SulphoraphaneHMDB
1-Isothiocyanato-4-methylsulphinylbutaneHMDB
MethylsulfoxybutylisothiocyanateHMDB
4-Methylsulphinylbutyl glucosinolateHMDB
Chemical FormulaC6H11NOS2
Average Molecular Mass177.288 g/mol
Monoisotopic Mass177.028 g/mol
CAS Registry Number4478-93-7
IUPAC Name1-isothiocyanato-4-methanesulfinylbutane
Traditional Namesulforaphane
SMILESCS(=O)CCCCN=C=S
InChI IdentifierInChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
InChI KeySUVMJBTUFCVSAD-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 Descriptors
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 Solubility2.55 g/LALOGPS
logP1.24ALOGPS
logP0.22ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.57 m³·mol⁻¹ChemAxon
Polarizability19.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 IDHMDB0005792
FooDB IDFDB012609
Phenol Explorer IDNot Available
KNApSAcK IDC00050239
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSulforaphane
Chemspider ID5157
ChEBI ID47807
PubChem Compound ID5350
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=16442570
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17134937
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18090122
4. Iori R; Bernardi R; Gueyrard D; Rollin P; Palmieri S Formation of glucoraphanin by chemoselective oxidation of natural glucoerucin: a chemoenzymatic route to sulforaphane. Bioorganic & medicinal chemistry letters (1999), 9(7), 1047-8.
5. Fimognari C, Hrelia P: Sulforaphane as a promising molecule for fighting cancer. Mutat Res. 2007 May-Jun;635(2-3):90-104. Epub 2006 Nov 28.