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Showing NP-Card for (1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene (NP0147847)

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Record Information
Version2.0
Created at2022-09-02 03:31:15 UTC
Updated at2022-09-02 03:31:16 UTC
NP-MRD IDNP0147847
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene
DescriptionThiosulfinate, also known as thiosulfinic 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). (1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene is found in Allium cepa. (1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene was first documented in 2022 (PMID: 35738490). Based on a literature review a small amount of articles have been published on thiosulfinate (PMID: 35276798) (PMID: 35255244) (PMID: 35107883) (PMID: 35077829).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0147847 ((1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene)


  Mrv1652309022205312D          

  9  8  0  0  0  0            999 V2000
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
M  CHG  2   5   1   6  -1
M  END
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3D MOL for NP0147847 ((1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene)

     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -3.8928   -0.6098   -0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5152   -0.0743   -0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2694    1.2217   -0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7261    2.0120   -0.2008 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728    0.6832    1.0318 S   0  0  0  0  0  3  0  0  0  0  0  0
    0.6722    1.4712    2.4265 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.7000    0.1797    0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939   -0.2884    0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -0.7489   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8364   -1.7220   -0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5730   -0.2917    0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683   -0.2540   -1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6654   -0.7130   -0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1477    1.8525   -0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7370    0.2064   -1.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8117   -0.3367    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9275   -1.8591   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9975   -0.3214   -1.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8856   -0.4075    0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  2  0
  8  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  3 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
  9 18  1  0
  9 19  1  0
M  CHG  2   5   1   6  -1
M  END
Download

3D SDF for NP0147847 ((1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene)


  Mrv1652309022205312D          

  9  8  0  0  0  0            999 V2000
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
M  CHG  2   5   1   6  -1
M  END
> <DATABASE_ID>
NP0147847

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\S[S+]([O-])\C=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-6H,1-2H3/b5-3+,6-4+

> <INCHI_KEY>
GYJUUWJKEUIYPF-GGWOSOGESA-N

> <FORMULA>
C6H10OS2

> <MOLECULAR_WEIGHT>
162.27

> <EXACT_MASS>
162.01730729

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
16.92150394026919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
0.9855172264573875

> <ALOGPS_LOGS>
-1.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.180047271666984

> <JCHEM_PKA_STRONGEST_BASIC>
-4.46964732337286

> <JCHEM_POLAR_SURFACE_AREA>
23.06

> <JCHEM_REFRACTIVITY>
45.3038

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.73e+00 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0147847 ((1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene)

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PDB for NP0147847 ((1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene)
HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       3.850   1.334   0.000  0.00  0.00           S+0
HETATM    5  S   UNK     0       2.310   1.334   0.000  0.00  0.00           S+1
HETATM    6  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O-1
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770  -1.334   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0147847 ((1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene)
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SMILES for NP0147847 ((1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene)
C\C=C\S[S+]([O-])\C=C\C
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INCHI for NP0147847 ((1e)-1-{[(1e)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene)
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-6H,1-2H3/b5-3+,6-4+
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View in JSmol
Synonyms
ValueSource
Thiosulfinic acidGenerator
ThiosulphinateGenerator
Thiosulphinic acidGenerator
Chemical FormulaC6H10OS2
Average Mass162.2700 Da
Monoisotopic Mass162.01731 Da
IUPAC Name(1E)-1-{[(1E)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene
Traditional Name(1E)-1-{[(1E)-prop-1-ene-1-sulfinyl]sulfanyl}prop-1-ene
CAS Registry NumberNot Available
SMILES
C\C=C\S[S+]([O-])\C=C\C
InChI Identifier
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-6H,1-2H3/b5-3+,6-4+
InChI KeyGYJUUWJKEUIYPF-GGWOSOGESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium cepaLOTUS Database
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
    • 

  • 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
logP1.58ALOGPS
logP0.99ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)11.18ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.3 m³·mol⁻¹ChemAxon
Polarizability16.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00054137  
Chemspider ID57503157  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThiosulfinate  
METLIN IDNot Available
PubChem Compound58219327  
PDB IDNot Available
ChEBI ID183507  
Good Scents IDNot Available
References
General References
  1. Morozova E, Abo Qoura L, Anufrieva N, Koval V, Lesnova E, Kushch A, Kulikova V, Revtovich S, Pokrovsky VS, Demidkina T: Daidzein-directed methionine gamma-lyase in enzyme prodrug therapy against breast cancer. Biochimie. 2022 Oct;201:177-183. doi: 10.1016/j.biochi.2022.05.007. Epub 2022 Jun  20. [PubMed:35738490  ] 
  2. Liebana-Garcia R, Olivares M, Rodriguez-Ruano SM, Tolosa-Enguis V, Chulia I, Gil-Martinez L, Guillamon E, Banos A, Sanz Y: The Allium Derivate Propyl Propane Thiosulfinate Exerts Anti-Obesogenic Effects in a Murine Model of Diet-Induced Obesity. Nutrients. 2022 Jan 19;14(3):440. doi: 10.3390/nu14030440. [PubMed:35276798  ] 
  3. Fernandez G, Sbres M, Lado J, Perez-Faggiani E: Postharvest sour rot control in lemon fruit by natamycin and an Allium extract. Int J Food Microbiol. 2022 May 2;368:109605. doi:  10.1016/j.ijfoodmicro.2022.109605. Epub 2022 Mar 1. [PubMed:35255244  ] 
  4. Zhu L, Myhill LJ, Andersen-Civil AIS, Thamsborg SM, Blanchard A, Williams AR: Garlic-Derived Organosulfur Compounds Regulate Metabolic and Immune Pathways in Macrophages and Attenuate Intestinal Inflammation in Mice. Mol Nutr Food Res. 2022 Apr;66(7):e2101004. doi: 10.1002/mnfr.202101004. Epub  2022 Mar 7. [PubMed:35107883  ] 
  5. Cascajosa-Lira A, Pichardo S, Banos A, Guillamon E, Molina-Hernandez V, Moyano R, Jos A, Camean AM: Acute and subchronic 90-days toxicity assessment of propyl-propane-thiosulfinate (PTS) in rats. Food Chem Toxicol. 2022 Mar;161:112827. doi: 10.1016/j.fct.2022.112827. Epub 2022  Jan 22. [PubMed:35077829  ] 
  6. LOTUS database [Link]