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Showing metabocard for Sulforaphane (HMDB0005792)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-01-22 21:33:44 UTC
Update Date2023-02-21 17:17:07 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005792 (Sulforaphane)

  Mrv1652305271900292D          

 10  9  0  0  0  0            999 V2000
    9.7991   -9.0820    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5136   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2280   -8.2570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9425   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6570   -8.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3714   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0859   -8.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8004   -8.6695    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5149   -8.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8004   -9.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
M  END
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3D MOL for HMDB0005792 (Sulforaphane)

HMDB0005792
     RDKit          3D
Sulforaphane
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.5517    0.7832    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261   -0.5850    0.6229 S   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0127   -1.8020   -0.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413   -0.1489   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1148   -1.2853    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -1.0321   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    0.1726    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    0.4935   -0.3759 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8591    1.6330   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5998    3.0695   -0.2629 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4488    1.1664   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6029    0.4714    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478    1.5890    1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899    0.7686    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9350    0.1118   -1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022   -2.2441   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -1.3707    1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928   -0.9254   -1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836   -1.9380   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.0083    1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4383    1.0641   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
M  END
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3D SDF for HMDB0005792 (Sulforaphane)

  Mrv1652305271900292D          

 10  9  0  0  0  0            999 V2000
    9.7991   -9.0820    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5136   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2280   -8.2570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9425   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6570   -8.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3714   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0859   -8.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8004   -8.6695    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5149   -8.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8004   -9.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005792

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C6H11NOS2

> <MOLECULAR_WEIGHT>
177.288

> <EXACT_MASS>
177.028205359

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
19.108731790879084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-isothiocyanato-4-methanesulfinylbutane

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
0.21977109100000025

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6321878230660762

> <JCHEM_POLAR_SURFACE_AREA>
29.43

> <JCHEM_REFRACTIVITY>
49.567699999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulforaphane

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0005792 (Sulforaphane)

HMDB0005792
     RDKit          3D
Sulforaphane
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.5517    0.7832    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261   -0.5850    0.6229 S   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0127   -1.8020   -0.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413   -0.1489   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1148   -1.2853    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -1.0321   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    0.1726    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    0.4935   -0.3759 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8591    1.6330   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5998    3.0695   -0.2629 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4488    1.1664   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6029    0.4714    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478    1.5890    1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899    0.7686    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9350    0.1118   -1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022   -2.2441   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -1.3707    1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928   -0.9254   -1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836   -1.9380   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.0083    1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4383    1.0641   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
M  END
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PDB for HMDB0005792 (Sulforaphane)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0      18.292 -16.953   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0      19.625 -16.183   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      20.959 -15.413   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      22.293 -16.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.626 -15.413   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.960 -16.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.294 -15.413   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0      27.627 -16.183   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0      28.961 -15.413   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      27.627 -17.723   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0005792 (Sulforaphane)

COMPND    HMDB0005792
HETATM    1  C1  UNL     1      -3.552   0.783   0.381  1.00  0.00           C  
HETATM    2  S1  UNL     1      -2.426  -0.585   0.623  1.00  0.00           S  
HETATM    3  O1  UNL     1      -3.013  -1.802  -0.109  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.841  -0.149  -0.123  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.115  -1.285   0.071  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.480  -1.032  -0.522  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.066   0.173   0.131  1.00  0.00           C  
HETATM    8  N1  UNL     1       3.395   0.493  -0.376  1.00  0.00           N  
HETATM    9  C6  UNL     1       3.859   1.633  -0.044  1.00  0.00           C  
HETATM   10  S2  UNL     1       4.600   3.070  -0.263  1.00  0.00           S  
HETATM   11  H1  UNL     1      -3.449   1.166  -0.668  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.603   0.471   0.588  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.248   1.589   1.080  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.490   0.769   0.396  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.935   0.112  -1.189  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.302  -2.244  -0.277  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.285  -1.371   1.185  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.393  -0.925  -1.621  1.00  0.00           H  
HETATM   19  H9  UNL     1       2.084  -1.938  -0.342  1.00  0.00           H  
HETATM   20  H10 UNL     1       2.144   0.008   1.212  1.00  0.00           H  
HETATM   21  H11 UNL     1       1.438   1.064  -0.136  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9    9
CONECT    9   10   10
END
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SMILES for HMDB0005792 (Sulforaphane)

CS(=O)CCCCN=C=S
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INCHI for HMDB0005792 (Sulforaphane)

InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
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
Source
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
Predicted Chromatographic Properties
Spectra
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)Not Available
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 ]