Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-01-22 21:33:44 UTC

Update Date

2023-02-21 17:17:07 UTC

HMDB ID

HMDB0005792

Secondary Accession Numbers

HMDB05792

Metabolite Identification

Common Name

Sulforaphane

Description

Sulforaphane (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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Sulforafan	ChEBI
Sulphorafan	Generator
Sulphoraphane	Generator
(R)-Sulphoraphane	HMDB
1-Isothiocyanato-4-methylsulphinylbutane	HMDB
Methylsulfoxybutylisothiocyanate	HMDB
4-Methylsulphinylbutyl glucosinolate	HMDB

Chemical Formula

C₆H₁₁NOS₂

Average Molecular Weight

177.288

Monoisotopic Molecular Weight

177.028205359

IUPAC Name

1-isothiocyanato-4-methanesulfinylbutane

Traditional Name

sulforaphane

CAS Registry Number

4478-93-7

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 Key

SUVMJBTUFCVSAD-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).

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Sulfoxides

Sub Class

Not Available

Direct Parent

Sulfoxides

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 Framework

Aliphatic acyclic compounds

External Descriptors

sulfoxide (CHEBI:47807 )
isothiocyanate (CHEBI:47807 )

Ontology

Not Available

Brassicas (FooDB: FOOD00857)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	368.00 to 369.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	13820 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.407 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.55 g/L	ALOGPS
logP	1.24	ALOGPS
logP	0.22	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	49.57 m³·mol⁻¹	ChemAxon
Polarizability	19.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.364	31661259
DarkChem	[M-H]-	132.781	31661259
DeepCCS	[M+H]+	135.124	30932474
DeepCCS	[M-H]-	132.892	30932474
DeepCCS	[M-2H]-	168.715	30932474
DeepCCS	[M+Na]+	143.709	30932474
AllCCS	[M+H]+	137.2	32859911
AllCCS	[M+H-H2O]+	133.5	32859911
AllCCS	[M+NH4]+	140.7	32859911
AllCCS	[M+Na]+	141.7	32859911
AllCCS	[M-H]-	140.8	32859911
AllCCS	[M+Na-2H]-	143.2	32859911
AllCCS	[M+HCOO]-	145.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulforaphane	CS(=O)CCCCN=C=S	2345.1	Standard polar	33892256
Sulforaphane	CS(=O)CCCCN=C=S	1567.4	Standard non polar	33892256
Sulforaphane	CS(=O)CCCCN=C=S	1528.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sulforaphane GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9200000000-13bb34bfb5f98523f06e	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulforaphane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-03k9-4900000000-742108ad95fbe3ca0e61	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane LC-ESI-QTOF , positive-QTOF	splash10-03k9-4900000000-742108ad95fbe3ca0e61	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-014i-9000000000-7966b27346fb428d53ee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-03fr-0900000000-af73321f81bddaf43612	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-03di-0900000000-f0da4b16134ff4652c8d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-014j-2900000000-fdc05deaaf8a3bb32535	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-03di-0900000000-225c7e29256c6a4934d0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-00di-9000000000-73be15346a4e5144e261	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-03di-0900000000-f3f4885c993126477f13	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-00di-9300000000-deedc73726d227f19f41	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-00di-9200000000-260a6d9d8aeff3f77df4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-03di-0900000000-0b0b8e45874beab607cf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-03di-0900000000-b2800c3f60c7b563bc5b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-03k9-6900000000-7b9f717a8d3956572b8d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Negative-QTOF	splash10-03di-0900000000-45a381b14aea32f3e7c8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 35V, Positive-QTOF	splash10-0229-9400000000-4c01aaa0876fd3eca279	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-03di-0900000000-9f7a884add20d9d6db31	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-0400-2900000000-3de54c87b48257b9e475	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulforaphane 6V, Positive-QTOF	splash10-03di-2900000000-213ad1b19418d48286a3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulforaphane 10V, Positive-QTOF	splash10-004i-1900000000-0c6d5f2ee2aaf8646546	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulforaphane 20V, Positive-QTOF	splash10-016r-3900000000-068b539328d9244f017d	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulforaphane 40V, Positive-QTOF	splash10-0a4i-9100000000-96f75c1a46ae1959b305	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulforaphane 10V, Negative-QTOF	splash10-03fr-9500000000-2be1c78cc874ea6f663a	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulforaphane 20V, Negative-QTOF	splash10-03di-9000000000-43a3325cb22657f00fbd	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulforaphane 40V, Negative-QTOF	splash10-08fr-9000000000-377cf68733d05500349a	2017-06-28	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.54 +/- 0.11 uM	Adult (>18 years old)	Both	Normal	16289008	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23657156	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012609

KNApSAcK ID

C00050239

Chemspider ID

5157

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulforaphane

METLIN ID

Not Available

PubChem Compound

5350

PDB ID

Not Available

ChEBI ID

47807

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1120281

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]

Showing metabocard for Sulforaphane (HMDB0005792)

MOL for HMDB0005792 (Sulforaphane)

3D MOL for HMDB0005792 (Sulforaphane)

3D SDF for HMDB0005792 (Sulforaphane)

3D-SDF for HMDB0005792 (Sulforaphane)

PDB for HMDB0005792 (Sulforaphane)

3D PDB for HMDB0005792 (Sulforaphane)

SMILES for HMDB0005792 (Sulforaphane)

INCHI for HMDB0005792 (Sulforaphane)

Structure for HMDB0005792 (Sulforaphane)

3D Structure for HMDB0005792 (Sulforaphane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra