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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-01-22 21:33:44 UTC
Update Date2017-12-07 01:55:30 UTC
HMDB IDHMDB0005792
Secondary Accession Numbers
  • HMDB05792
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
(R)-SulphoraphaneGenerator
1-isothiocyanato-4-MethylsulphinylbutaneMeSH
MethylsulfoxybutylisothiocyanateMeSH
SulphoraphaneMeSH
4-Methylsulphinylbutyl glucosinolateMeSH
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 KeySUVMJBTUFCVSAD-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 Descriptors
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 Solubility2.55 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
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, Positivesplash10-03di-9200000000-13bb34bfb5f98523f06eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03k9-4900000000-742108ad95fbe3ca0e61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03k9-4900000000-742108ad95fbe3ca0e61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-0c6d5f2ee2aaf8646546View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-3900000000-068b539328d9244f017dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-96f75c1a46ae1959b305View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-9500000000-2be1c78cc874ea6f663aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-43a3325cb22657f00fbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-9000000000-377cf68733d05500349aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.54 +/- 0.11 uMAdult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
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
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. [PubMed:17134937 ]