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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-01-22 21:33:44 UTC
Update Date2022-03-07 02:49:29 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
Data?1582752365
Synonyms
ValueSource
SulforafanChEBI
SulphorafanGenerator
SulphoraphaneGenerator
(R)-SulphoraphaneHMDB
1-Isothiocyanato-4-methylsulphinylbutaneHMDB
MethylsulfoxybutylisothiocyanateHMDB
4-Methylsulphinylbutyl glucosinolateHMDB
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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point368.00 to 369.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility13820 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.407 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.36431661259
DarkChem[M-H]-132.78131661259
DeepCCS[M+H]+135.12430932474
DeepCCS[M-H]-132.89230932474
DeepCCS[M-2H]-168.71530932474
DeepCCS[M+Na]+143.70930932474
AllCCS[M+H]+137.232859911
AllCCS[M+H-H2O]+133.532859911
AllCCS[M+NH4]+140.732859911
AllCCS[M+Na]+141.732859911
AllCCS[M-H]-140.832859911
AllCCS[M+Na-2H]-143.232859911
AllCCS[M+HCOO]-145.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulforaphaneCS(=O)CCCCN=C=S2345.1Standard polar33892256
SulforaphaneCS(=O)CCCCN=C=S1567.4Standard non polar33892256
SulforaphaneCS(=O)CCCCN=C=S1528.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulforaphane GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9200000000-13bb34bfb5f98523f06e2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulforaphane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-03k9-4900000000-742108ad95fbe3ca0e612012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane LC-ESI-QTOF , positive-QTOFsplash10-03k9-4900000000-742108ad95fbe3ca0e612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-014i-9000000000-7966b27346fb428d53ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-03fr-0900000000-af73321f81bddaf436122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-03di-0900000000-f0da4b16134ff4652c8d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-014j-2900000000-fdc05deaaf8a3bb325352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-03di-0900000000-225c7e29256c6a4934d02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-00di-9000000000-73be15346a4e5144e2612021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-03di-0900000000-f3f4885c993126477f132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-00di-9300000000-deedc73726d227f19f412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-00di-9200000000-260a6d9d8aeff3f77df42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-03di-0900000000-0b0b8e45874beab607cf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-03di-0900000000-b2800c3f60c7b563bc5b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-03k9-6900000000-7b9f717a8d3956572b8d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Negative-QTOFsplash10-03di-0900000000-45a381b14aea32f3e7c82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 35V, Positive-QTOFsplash10-0229-9400000000-4c01aaa0876fd3eca2792021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-03di-0900000000-9f7a884add20d9d6db312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-0400-2900000000-3de54c87b48257b9e4752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOFsplash10-03di-2900000000-213ad1b19418d48286a32021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulforaphane 10V, Positive-QTOFsplash10-004i-1900000000-0c6d5f2ee2aaf86465462017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulforaphane 20V, Positive-QTOFsplash10-016r-3900000000-068b539328d9244f017d2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulforaphane 40V, Positive-QTOFsplash10-0a4i-9100000000-96f75c1a46ae1959b3052017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulforaphane 10V, Negative-QTOFsplash10-03fr-9500000000-2be1c78cc874ea6f663a2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulforaphane 20V, Negative-QTOFsplash10-03di-9000000000-43a3325cb22657f00fbd2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulforaphane 40V, Negative-QTOFsplash10-08fr-9000000000-377cf68733d05500349a2017-06-28Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.54 +/- 0.11 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012609
KNApSAcK IDC00050239
Chemspider ID5157
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulforaphane
METLIN IDNot Available
PubChem Compound5350
PDB IDNot Available
ChEBI ID47807
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1120281
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 ]