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Showing NP-Card for R-2-Propenyl 1-propenesulfinothioate (NP0047455)

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Record Information
Version2.0
Created at2022-03-17 20:40:30 UTC
Updated at2022-03-17 20:40:30 UTC
NP-MRD IDNP0047455
Secondary Accession NumbersNone
Natural Product Identification
Common NameR-2-Propenyl 1-propenesulfinothioate
DescriptionR-2-Propenyl 1-propenesulfinothioate, also known as 5-bromo-protocatechuic acid or 3-bromo-4,5-dihydroxybenzoic acid, belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl). R-2-Propenyl 1-propenesulfinothioate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, R-2-Propenyl 1-propenesulfinothioate has been detected, but not quantified in, onion-family vegetables. This could make R-2-propenyl 1-propenesulfinothioate a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047455 (R-2-Propenyl 1-propenesulfinothioate)


  Mrv0541 05061306402D          

  9  8  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
M  END
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3D MOL for NP0047455 (R-2-Propenyl 1-propenesulfinothioate)

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3D SDF for NP0047455 (R-2-Propenyl 1-propenesulfinothioate)

  Mrv0541 05061306402D          

  9  8  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047455

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C/S(=O)SCC=C

> <INCHI_IDENTIFIER>
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4,6H,1,5H2,2H3/b6-4-

> <INCHI_KEY>
MMTFXWIIILIGFN-XQRVVYSFSA-N

> <FORMULA>
C6H10OS2

> <MOLECULAR_WEIGHT>
162.273

> <EXACT_MASS>
162.017306322

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.531463522363865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(1Z)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
2.3670000000000004

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.576628222305661

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
45.063

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1Z)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047455 (R-2-Propenyl 1-propenesulfinothioate)
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PDB for NP0047455 (R-2-Propenyl 1-propenesulfinothioate)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.645  -0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       3.644   2.104   0.000  0.00  0.00           S+0
HETATM    9  S   UNK     0       4.977   1.334   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    9                                                       
CONECT    7    9                                                            
CONECT    8    5    9                                                       
CONECT    9    6    7    8                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0047455 (R-2-Propenyl 1-propenesulfinothioate)
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SMILES for NP0047455 (R-2-Propenyl 1-propenesulfinothioate)
C\C=C/S(=O)SCC=C
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INCHI for NP0047455 (R-2-Propenyl 1-propenesulfinothioate)
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4,6H,1,5H2,2H3/b6-4-
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Synonyms
ValueSource
R-2-Propenyl 1-propenesulfinothioic acidGenerator
R-2-Propenyl 1-propenesulphinothioateGenerator
R-2-Propenyl 1-propenesulphinothioic acidGenerator
3-Bromo-4,5-dihydroxybenzoic acidHMDB
5-Bromo-3,4-dihydroxybenzoic acidHMDB
5-Bromo-protocatechuic acidHMDB
5-Bromoprotocatechuic acidHMDB
Sodium 1,4-bis(trimethylhexyl) sulphonatosuccinateHMDB
3-{[(1Z)-prop-1-ene-1-sulphinyl]sulphanyl}prop-1-eneGenerator
Chemical FormulaC6H10OS2
Average Mass162.2730 Da
Monoisotopic Mass162.01731 Da
IUPAC Name3-{[(1Z)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene
Traditional Name3-{[(1Z)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene
CAS Registry Number143038-12-4
SMILES
C\C=C/S(=O)SCC=C
InChI Identifier
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4,6H,1,5H2,2H3/b6-4-
InChI KeyMMTFXWIIILIGFN-XQRVVYSFSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium cepaFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium fistulosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassThiosulfinic acid esters  
Sub ClassNot Available
Direct ParentThiosulfinic acid esters  
Alternative Parents
Substituents
  • Thiosulfinic acid ester
    • 

  • Allyl sulfur compound
    • 

  • Sulfenyl compound
    • 

  • Sulfinyl compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.61ALOGPS
logP2.37ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity45.06 m³·mol⁻¹ChemAxon
Polarizability16.53 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032752  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010718  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound88088040  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available