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Showing NP-Card for S-Propyl 1-propanesulfinothioate (NP0047959)

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Record Information
Version2.0
Created at2022-03-17 20:48:44 UTC
Updated at2022-03-17 20:48:44 UTC
NP-MRD IDNP0047959
Secondary Accession NumbersNone
Natural Product Identification
Common NameS-Propyl 1-propanesulfinothioate
DescriptionS-Propyl 1-propanesulfinothioate, also known as S-propyl propane-1-thiosulfinate or propyl propylthiosulfinic 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). A sulfinic acid derivative obtained by formal condensation of propanethiosulfinic acid with propanethiol. S-Propyl 1-propanesulfinothioate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, S-Propyl 1-propanesulfinothioate has been detected, but not quantified in, onion-family vegetables. S-Propyl 1-propanesulfinothioate is found in Allium schoenoprasum. S-Propyl 1-propanesulfinothioate was first documented in 2000 (PMID: 10820136). This could make S-propyl 1-propanesulfinothioate a potential biomarker for the consumption of these foods (PMID: 21445384).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047959 (S-Propyl 1-propanesulfinothioate)


  Mrv0541 05061307472D          

  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
    4.8099    1.1270    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  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  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 NP0047959 (S-Propyl 1-propanesulfinothioate)

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3D SDF for NP0047959 (S-Propyl 1-propanesulfinothioate)

  Mrv0541 05061307472D          

  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
    4.8099    1.1270    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  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  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>
NP0047959

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCSS(=O)CCC

> <INCHI_IDENTIFIER>
InChI=1S/C6H14OS2/c1-3-5-8-9(7)6-4-2/h3-6H2,1-2H3

> <INCHI_KEY>
XPRZAEWSYWTDSQ-UHFFFAOYSA-N

> <FORMULA>
C6H14OS2

> <MOLECULAR_WEIGHT>
166.305

> <EXACT_MASS>
166.04860645

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.654154948884845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(propane-1-sulfinyl)sulfanyl]propane

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
2.1624

> <ALOGPS_LOGS>
-1.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.62628820907052

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
45.1524

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(propane-1-sulfinyl)sulfanyl]propane

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047959 (S-Propyl 1-propanesulfinothioate)
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PDB for NP0047959 (S-Propyl 1-propanesulfinothioate)
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       8.978   2.104   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 NP0047959 (S-Propyl 1-propanesulfinothioate)
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SMILES for NP0047959 (S-Propyl 1-propanesulfinothioate)
CCCSS(=O)CCC
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INCHI for NP0047959 (S-Propyl 1-propanesulfinothioate)
InChI=1S/C6H14OS2/c1-3-5-8-9(7)6-4-2/h3-6H2,1-2H3
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Synonyms
ValueSource
1-Propanesulfinothioic acid, S-propyl esterChEBI
Dipropyl thiosulfinateChEBI
Propyl propanethiosulfinateChEBI
Propyl propylthiosulfinateChEBI
S-Propyl propane-1-thiosulfinateChEBI
1-Propanesulfinothioate, S-propyl esterGenerator
1-Propanesulphinothioate, S-propyl esterGenerator
1-Propanesulphinothioic acid, S-propyl esterGenerator
Dipropyl thiosulfinic acidGenerator
Dipropyl thiosulphinateGenerator
Dipropyl thiosulphinic acidGenerator
Propyl propanethiosulfinic acidGenerator
Propyl propanethiosulphinateGenerator
Propyl propanethiosulphinic acidGenerator
Propyl propylthiosulfinic acidGenerator
Propyl propylthiosulphinateGenerator
Propyl propylthiosulphinic acidGenerator
S-Propyl propane-1-thiosulfinic acidGenerator
S-Propyl propane-1-thiosulphinateGenerator
S-Propyl propane-1-thiosulphinic acidGenerator
S-Propyl 1-propanesulfinothioic acidGenerator
S-Propyl 1-propanesulphinothioateGenerator
S-Propyl 1-propanesulphinothioic acidGenerator
O-BenzoylthiamineHMDB
S-Propyl 1-propanesulfinothioate, 9ciHMDB
S-Propyl 1-propanesulfinothioateChEBI
S-Propyl propanethiosulfinic acidGenerator
S-Propyl propanethiosulphinateGenerator
S-Propyl propanethiosulphinic acidGenerator
Chemical FormulaC6H14OS2
Average Mass166.3050 Da
Monoisotopic Mass166.04861 Da
IUPAC Name1-[(propane-1-sulfinyl)sulfanyl]propane
Traditional Name1-[(propane-1-sulfinyl)sulfanyl]propane
CAS Registry Number1948-52-3
SMILES
CCCSS(=O)CCC
InChI Identifier
InChI=1S/C6H14OS2/c1-3-5-8-9(7)6-4-2/h3-6H2,1-2H3
InChI KeyXPRZAEWSYWTDSQ-UHFFFAOYSA-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...
Allium schoenoprasumLOTUS 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
logP1.61ALOGPS
logP2.16ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity45.15 m³·mol⁻¹ChemAxon
Polarizability18.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034394  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012782  
KNApSAcK IDNot Available
Chemspider ID67333  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74761  
PDB IDNot Available
ChEBI ID91021  
Good Scents IDNot Available
References
General References
  1. Teyssier C, Siess MH: Metabolism of dipropyl disulfide by rat liver phase I and phase II enzymes and by isolated perfused rat liver. Drug Metab Dispos. 2000 Jun;28(6):648-54. [PubMed:10820136  ] 
  2. Lynett PT, Butts K, Vaidya V, Garrett GE, Pratt DA: The mechanism of radical-trapping antioxidant activity of plant-derived thiosulfinates. Org Biomol Chem. 2011 May 7;9(9):3320-30. doi: 10.1039/c1ob05192j. Epub 2011 Mar  28. [PubMed:21445384  ]