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Showing metabocard for (R)-(E)-Sulforaphene (HMDB0031573)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:08 UTC
Update Date2023-02-21 17:20:53 UTC
HMDB IDHMDB0031573
Secondary Accession Numbers
  • HMDB31573
Metabolite Identification
Common Name(R)-(E)-Sulforaphene
Description(R)-(E)-Sulforaphene, also known as sulforaphene, 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) (R)-(E)-Sulforaphene has been detected, but not quantified in, root vegetables. This could make (R)-(e)-sulforaphene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-(E)-Sulforaphene.
Structure
Data?1677000053
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031573 ((R)-(E)-Sulforaphene)


  Mrv1652309211809262D          

 10  9  0  0  0  0            999 V2000
   -2.8582   -0.2062    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    0.6187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    0.2062    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436   -0.6187    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  2  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 HMDB0031573 ((R)-(E)-Sulforaphene)

HMDB0031573
     RDKit          3D
(R)-(E)-Sulforaphene
 19 18  0  0  0  0  0  0  0  0999 V2000
   -3.4341   -0.3182    0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -0.2138    1.5690 S   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5696   -1.3552    2.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6688    0.0222    1.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2084   -0.0460   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237    0.1560   -0.4577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8057   -1.0671   -1.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069   -0.7427   -1.4229 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9117   -0.3768   -0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8475   -0.0155    0.8476 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4406   -0.6185    0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485    0.6542   -0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -1.1180   -0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0283    0.2377    1.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056   -0.2616   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2818    0.9874   -1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086    0.3965    0.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004   -1.3024   -2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8117   -1.9351   -0.4663 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  2  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
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
M  END
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3D SDF for HMDB0031573 ((R)-(E)-Sulforaphene)


  Mrv1652309211809262D          

 10  9  0  0  0  0            999 V2000
   -2.8582   -0.2062    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    0.6187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    0.2062    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436   -0.6187    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  2  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>
HMDB0031573

> <DATABASE_NAME>
hmdb

> <SMILES>
CS(=O)\C=C\CCN=C=S

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NOS2/c1-10(8)5-3-2-4-7-6-9/h3,5H,2,4H2,1H3/b5-3+

> <INCHI_KEY>
QKGJFQMGPDVOQE-HWKANZROSA-N

> <FORMULA>
C6H9NOS2

> <MOLECULAR_WEIGHT>
175.272

> <EXACT_MASS>
175.012555295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
18.132124300217548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E)-4-isothiocyanato-1-methanesulfinylbut-1-ene

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
0.307234390666667

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.795372571421226

> <JCHEM_POLAR_SURFACE_AREA>
29.43

> <JCHEM_REFRACTIVITY>
49.69859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
raphanin

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0031573 ((R)-(E)-Sulforaphene)

HMDB0031573
     RDKit          3D
(R)-(E)-Sulforaphene
 19 18  0  0  0  0  0  0  0  0999 V2000
   -3.4341   -0.3182    0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -0.2138    1.5690 S   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5696   -1.3552    2.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6688    0.0222    1.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2084   -0.0460   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237    0.1560   -0.4577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8057   -1.0671   -1.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069   -0.7427   -1.4229 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9117   -0.3768   -0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8475   -0.0155    0.8476 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4406   -0.6185    0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485    0.6542   -0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -1.1180   -0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0283    0.2377    1.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056   -0.2616   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2818    0.9874   -1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086    0.3965    0.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004   -1.3024   -2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8117   -1.9351   -0.4663 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  2  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
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
M  END
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PDB for HMDB0031573 ((R)-(E)-Sulforaphene)

HEADER    PROTEIN                                 21-SEP-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-SEP-18         0                                  
HETATM    1  S   UNK     0      -5.335  -0.385   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0      -4.001   0.385   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.668   1.155   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.334   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.668   1.155   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       4.001   0.385   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0       5.335   1.155   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -1.155   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 HMDB0031573 ((R)-(E)-Sulforaphene)

COMPND    HMDB0031573
HETATM    1  C1  UNL     1      -3.434  -0.318   0.147  1.00  0.00           C  
HETATM    2  S1  UNL     1      -2.363  -0.214   1.569  1.00  0.00           S  
HETATM    3  O1  UNL     1      -2.570  -1.355   2.520  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.669   0.022   1.123  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.208  -0.046  -0.100  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.224   0.156  -0.458  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.806  -1.067  -1.124  1.00  0.00           C  
HETATM    8  N1  UNL     1       3.207  -0.743  -1.423  1.00  0.00           N  
HETATM    9  C6  UNL     1       3.912  -0.377  -0.416  1.00  0.00           C  
HETATM   10  S2  UNL     1       4.847  -0.015   0.848  1.00  0.00           S  
HETATM   11  H1  UNL     1      -4.441  -0.618   0.508  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.549   0.654  -0.366  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.088  -1.118  -0.565  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.028   0.238   1.924  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.906  -0.262  -0.903  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.282   0.987  -1.203  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.809   0.396   0.453  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.300  -1.302  -2.068  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.812  -1.935  -0.466  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7   16   17
CONECT    7    8   18   19
CONECT    8    9    9
CONECT    9   10   10
END
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SMILES for HMDB0031573 ((R)-(E)-Sulforaphene)

CS(=O)\C=C\CCN=C=S
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INCHI for HMDB0031573 ((R)-(E)-Sulforaphene)

InChI=1S/C6H9NOS2/c1-10(8)5-3-2-4-7-6-9/h3,5H,2,4H2,1H3/b5-3+
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(R)-(e)-SulphorapheneGenerator
SulphorapheneHMDB
(1E)-4-Isothiocyanato-1-methanesulphinylbut-1-eneHMDB
SulforapheneHMDB
Chemical FormulaC6H9NOS2
Average Molecular Weight175.272
Monoisotopic Molecular Weight175.012555295
IUPAC Name(1E)-4-isothiocyanato-1-methanesulfinylbut-1-ene
Traditional Nameraphanin
CAS Registry Number2404-46-8
SMILES
CS(=O)\C=C\CCN=C=S
InChI Identifier
InChI=1S/C6H9NOS2/c1-10(8)5-3-2-4-7-6-9/h3,5H,2,4H2,1H3/b5-3+
InChI KeyQKGJFQMGPDVOQE-HWKANZROSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.89 g/LALOGPS
logP1.62ALOGPS
logP0.31ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.7 m³·mol⁻¹ChemAxon
Polarizability18.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+130.55130932474
DeepCCS[M-H]-128.2830932474
DeepCCS[M-2H]-163.96630932474
DeepCCS[M+Na]+138.70230932474
AllCCS[M+H]+137.232859911
AllCCS[M+H-H2O]+133.432859911
AllCCS[M+NH4]+140.732859911
AllCCS[M+Na]+141.732859911
AllCCS[M-H]-139.232859911
AllCCS[M+Na-2H]-141.532859911
AllCCS[M+HCOO]-144.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.38 minutes32390414
Predicted by Siyang on May 30, 20228.726 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.37 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid136.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid837.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid305.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid98.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid187.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid62.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid254.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid284.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)489.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid646.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid123.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid883.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid193.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid234.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate613.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA321.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water159.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-(E)-SulforapheneCS(=O)\C=C\CCN=C=S2365.7Standard polar33892256
(R)-(E)-SulforapheneCS(=O)\C=C\CCN=C=S1524.5Standard non polar33892256
(R)-(E)-SulforapheneCS(=O)\C=C\CCN=C=S1507.2Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008194
KNApSAcK IDC00053805
Chemspider ID4938389
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6433206
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .