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Showing NP-Card for Divinyl sulfide (NP0047787)

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Record Information
Version2.0
Created at2022-03-17 20:45:58 UTC
Updated at2022-03-17 20:45:58 UTC
NP-MRD IDNP0047787
Secondary Accession NumbersNone
Natural Product Identification
Common NameDivinyl sulfide
DescriptionDivinyl sulfide, also known as (CH2=ch)2S or divinyl thioether, belongs to the class of organic compounds known as thioenol ethers. Thioenol ethers are compounds containing the enol ether functional group, with the formula R3SCR2=CR1. Divinyl sulfide is the organosulfur compound with the formula S(CHCH2)2. Divinyl sulfide is possibly neutral. Outside of the human body, Divinyl sulfide has been detected, but not quantified in, onion-family vegetables. This could make divinyl sulfide a potential biomarker for the consumption of these foods. Divinylsulfide was first prepared in 1920 by the reaction of sulfur mustard with sodium ethoxide:(ClCH2CH2)2S + 2 NaOEt → (CH2CH)2S + 2 EtOH + 2 NaClA variety of monovinyl sulfides are known, often arising from the reactions of thiols and acetylenes. It is notable as the product from hydrogen sulfide and acetylene, a combination that arises when acetylene is generated by hydrolysis of technical grade calcium carbide, which contains impurities of calcium sulfide. Divinyl sulfide is found in Allium spp. It is a colorless liquid with a faint odor.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047787 (Divinyl sulfide)


  Mrv0541 05061307272D          

  5  4  0  0  0  0            999 V2000
   -1.2375   -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
   -0.4125   -0.7145    0.0000 C   0  0  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 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
M  END
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3D MOL for NP0047787 (Divinyl sulfide)

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3D SDF for NP0047787 (Divinyl sulfide)

  Mrv0541 05061307272D          

  5  4  0  0  0  0            999 V2000
   -1.2375   -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
   -0.4125   -0.7145    0.0000 C   0  0  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 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047787

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C=CSC=C

> <INCHI_IDENTIFIER>
InChI=1S/C4H6S/c1-3-5-4-2/h3-4H,1-2H2

> <INCHI_KEY>
UIYCHXAGWOYNNA-UHFFFAOYSA-N

> <FORMULA>
C4H6S

> <MOLECULAR_WEIGHT>
86.155

> <EXACT_MASS>
86.019020882

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
9.401472840949577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(ethenylsulfanyl)ethene

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
1.4568505896666664

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
26.7581

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,1'-thiobisethene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047787 (Divinyl sulfide)
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PDB for NP0047787 (Divinyl sulfide)
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      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    5                                                       
CONECT    5    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END

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3D PDB for NP0047787 (Divinyl sulfide)
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SMILES for NP0047787 (Divinyl sulfide)
C=CSC=C
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INCHI for NP0047787 (Divinyl sulfide)
InChI=1S/C4H6S/c1-3-5-4-2/h3-4H,1-2H2
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View in JSmol
Synonyms
ValueSource
Divinyl sulphideGenerator
(CH2=ch)2SHMDB
1,1'-Thiobis-etheneHMDB
1,1'-ThiobisetheneHMDB
1,1'-Thiobisethene, 9ciHMDB
1-(Vinylsulfanyl)ethyleneHMDB
3-Thia-1,4-pentadieneHMDB
Diethenyl sulfideHMDB
Divinyl thioetherHMDB
Vinyl sulfideHMDB
Vinyl sulfide, 8ciHMDB
(Ethenylsulphanyl)etheneGenerator
ThiiraneMeSH
Divinyl sulfideMeSH
DivinylsulfideMeSH
Ethylene sulfideMeSH
Chemical FormulaC4H6S
Average Mass86.1550 Da
Monoisotopic Mass86.01902 Da
IUPAC Name(ethenylsulfanyl)ethene
Traditional Name1,1'-thiobisethene
CAS Registry Number627-51-0
SMILES
C=CSC=C
InChI Identifier
InChI=1S/C4H6S/c1-3-5-4-2/h3-4H,1-2H2
InChI KeyUIYCHXAGWOYNNA-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 spp.Plant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thioenol ethers. Thioenol ethers are compounds containing the enol ether functional group, with the formula R3SCR2=CR1.
KingdomOrganic compounds  
Super ClassOrganosulfur compounds  
ClassThioethers  
Sub ClassThioenol ethers  
Direct ParentThioenol ethers  
Alternative Parents
Substituents
  • Thioenolether
    • 

  • Sulfenyl compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP2ALOGPS
logP1.46ChemAxon
logS-1.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.76 m³·mol⁻¹ChemAxon
Polarizability9.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033922  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012121  
KNApSAcK IDNot Available
Chemspider ID11817  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDivinyl sulfide  
METLIN IDNot Available
PubChem Compound12321  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available