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Record Information
Version3.6
Creation Date2007-01-22 21:33:44 UTC
Update Date2016-02-11 01:07:16 UTC
HMDB IDHMDB05792
Secondary Accession NumbersNone
Metabolite Identification
Common NameSulforaphane
DescriptionSulforaphane (SFN) is the most characterized isothiocyanate. SFN has received a great deal of attention because of its ability to simultaneously modulate multiple cellular targets involved in cancer development, including: (i) DNA protection by modulating carcinogen-metabolizing enzymes and blocking the action of mutagens; (ii) inhibition of cell proliferation and induction of apoptosis, thereby retarding or eliminating clonal expansion of initiated, transformed, and/or neoplastic cells; (iii) inhibition of neoangiogenesis, progression of benign tumors to malignant tumors, and metastasis formation. SFN is therefore able to prevent, delay, or reverse preneoplastic lesions, as well as to act on cancer cells as a therapeutic agent. Taking into account this evidence and its favorable toxicological profile, SFN can be viewed as a conceptually promising agent in cancer prevention and/or therapy. SFN is the hydrolysis product of glucoraphanin, particularly high in the young sprouts of broccoli and cauliflower. SFN can also 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. (PMID: 17134937 ).
Structure
Thumb
Synonyms
ValueSource
SulforafanChEBI
SulphorafanGenerator
SulphoraphaneGenerator
1-isothiocyanato-4-(Methylsulfinyl)-butaneHMDB
1-isothiocyanato-4-(Methylsulfinyl)butaneHMDB
4-Methylsulfinyl butyl isothiocyanateHMDB
DL-SulforaphaneHMDB
SFNHMDB
SulforathaneHMDB
Chemical FormulaC6H11NOS2
Average Molecular Weight177.288
Monoisotopic Molecular Weight177.028205359
IUPAC Name1-isothiocyanato-4-methanesulfinylbutane
Traditional Namesulforaphane
CAS Registry Number4478-93-7
SMILES
CS(=O)CCCCN=C=S
InChI Identifier
InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
InChI KeyInChIKey=SUVMJBTUFCVSAD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sulfoxides. These 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
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Food
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility2.55 mg/mLALOGPS
logP1.24ALOGPS
logP0.22ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.57 m3·mol-1ChemAxon
Polarizability19.11 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03k9-4900000000-742108ad95fbe3ca0e61View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.54 +/- 0.11 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 IDFDB012608
KNApSAcK IDNot Available
Chemspider ID5157
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulforaphane
NuGOwiki LinkHMDB05792
Metagene LinkHMDB05792
METLIN IDNot Available
PubChem Compound5350
PDB IDNot Available
ChEBI ID47807
References
Synthesis ReferenceIori 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [17134937 ]