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Sulforaphane (FDB012608)

Record Information
Version1.0
Creation date2010-04-08 22:10:16 UTC
Update date2019-11-26 03:07:11 UTC
Primary IDFDB012608
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]. Sulforaphane is found in many foods, some of which are brussel sprouts, white cabbage, broccoli, and cabbage.
CAS Number4478-93-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H11NOS2
IUPAC name1-isothiocyanato-4-methanesulfinylbutane
InChI IdentifierInChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
InChI KeySUVMJBTUFCVSAD-UHFFFAOYSA-N
Isomeric SMILESCS(=O)CCCCN=C=S
Average Molecular Weight177.288
Monoisotopic Molecular Weight177.028205359
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Foods

Fruits and vegetables:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.65%; H 6.25%; N 7.90%; O 9.02%; S 36.17%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSulforaphane, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-9200000000-13bb34bfb5f98523f06eSpectrum
Predicted GC-MSSulforaphane, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03k9-4900000000-742108ad95fbe3ca0e612012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03k9-4900000000-742108ad95fbe3ca0e612017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-9000000000-7966b27346fb428d53ee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03fr-0900000000-af73321f81bddaf436122021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0900000000-f0da4b16134ff4652c8d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014j-2900000000-fdc05deaaf8a3bb325352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0900000000-225c7e29256c6a4934d02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-9000000000-73be15346a4e5144e2612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0900000000-f3f4885c993126477f132021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-9300000000-deedc73726d227f19f412021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-9200000000-260a6d9d8aeff3f77df42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0900000000-0b0b8e45874beab607cf2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0900000000-b2800c3f60c7b563bc5b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03k9-6900000000-7b9f717a8d3956572b8d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-03di-0900000000-45a381b14aea32f3e7c82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0229-9400000000-4c01aaa0876fd3eca2792021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0900000000-9f7a884add20d9d6db312021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0400-2900000000-3de54c87b48257b9e4752021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-2900000000-213ad1b19418d48286a32021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-0c6d5f2ee2aaf86465462017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-3900000000-068b539328d9244f017d2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-96f75c1a46ae1959b3052017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-9500000000-2be1c78cc874ea6f663a2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-43a3325cb22657f00fbd2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-9000000000-377cf68733d05500349a2017-06-28View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID5157
ChEMBL IDCHEMBL48802
KEGG Compound IDNot Available
Pubchem Compound ID5350
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05792
CRC / DFC (Dictionary of Food Compounds) IDHJH46-I:HJH46-I
EAFUS IDNot Available
Dr. Duke IDSULFORAPHANE|4-METHYL-SULFINYL-BUTYL-ISOTHIOCYANATE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
quinone-reductase inducerDUKE
anti neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).