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Showing NP-Card for 1,2-Ethanedithiol (NP0338318)

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Record Information
Version2.0
Created at2024-09-11 14:53:09 UTC
Updated at2024-09-11 14:53:10 UTC
NP-MRD IDNP0338318
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,2-Ethanedithiol
Description1,2-Ethanedithiol, also known as ethylene dimercaptan or 1,2-dimercaptoethane, belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain. As a 1,2-dithiol, this compound is widely used in organic chemistry because it reacts with aldehydes and ketones to give 1,3-dithiolanes, which are useful intermediates. Diols such as ethylene glycol undergo analogous reactions to 1,3-dioxolanes and 1,3-dioxanes. 1,2-Ethanedithiol is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,2-Ethanedithiol is a sulfury tasting compound. Outside of the human body,. One distinguishing feature of the dithiolanes and dithianes derived from aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated.1,2-Ethanedithiol is commonly used as a scavenger in peptide cleavage synthesis. It is a common building block in organic synthesis and an excellent ligand for metal ions.1,2-Ethanedithiol is prepared commercially by the reaction of 1,2-dichloroethane with aqueous sodium bisulfide. It has a very characteristic odor which is compared by many people to rotten cabbage. In the laboratory, it can also be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis. C2H4(SH)2 + RR'CO → C2H4S2CRR' + H2OOther 1,2- and 1,3-dithiols undergo this reaction to give related 1,3-dithiolanes and 1,3-dithianes (six-membered rings).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0338318 (1,2-Ethanedithiol)


  Mrv0541 05061306052D          

  4  3  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
    0.8250    0.0000    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
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
M  END
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3D MOL for NP0338318 (1,2-Ethanedithiol)

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3D SDF for NP0338318 (1,2-Ethanedithiol)

  Mrv0541 05061306052D          

  4  3  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
    0.8250    0.0000    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
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338318

> <DATABASE_NAME>
NP-MRD

> <SMILES>
SCCS

> <INCHI_IDENTIFIER>
InChI=1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2

> <INCHI_KEY>
VYMPLPIFKRHAAC-UHFFFAOYSA-N

> <FORMULA>
C2H6S2

> <MOLECULAR_WEIGHT>
94.199

> <EXACT_MASS>
93.991091572

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
10.248379609834622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethane-1,2-dithiol

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.9822447913333332

> <ALOGPS_LOGS>
-1.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.583850843790062

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.81252931715675

> <JCHEM_PKA_STRONGEST_BASIC>
-9.588044109484688

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
26.9188

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-ethanedithiol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0338318 (1,2-Ethanedithiol)
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PDB for NP0338318 (1,2-Ethanedithiol)
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       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       3.850  -1.334   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END

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3D PDB for NP0338318 (1,2-Ethanedithiol)
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SMILES for NP0338318 (1,2-Ethanedithiol)
SCCS
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INCHI for NP0338318 (1,2-Ethanedithiol)
InChI=1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2
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Synonyms
ValueSource
1,2-DimercaptoethaneHMDB
1,2-Dithiol ethaneHMDB
1,2-EthanethiolHMDB
alpha-Ethylene dimercaptanHMDB
Dithio-ethylene glycolHMDB
Dithioethylene glycolHMDB
Ethylene dimercaptanHMDB
Ethylene dithioglycolHMDB
Ethylene mercaptanHMDB
EthylenedimercaptanHMDB
EthylenedithiolHMDB
FEMA 3484HMDB
2-Mercaptoethanol disulfideMeSH
BisEDTMeSH
Bismuth ethanedithiolMeSH
EthanedithiolMeSH
1,2-EthanedithiolMeSH
EthandithiolMeSH
Chemical FormulaC2H6S2
Average Mass94.1990 Da
Monoisotopic Mass93.99109 Da
IUPAC Nameethane-1,2-dithiol
Traditional Name1,2-ethanedithiol
CAS Registry NumberNot Available
SMILES
SCCS
InChI Identifier
InChI=1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2
InChI KeyVYMPLPIFKRHAAC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.
KingdomOrganic compounds  
Super ClassOrganosulfur compounds  
ClassThiols  
Sub ClassAlkylthiols  
Direct ParentAlkylthiols  
Alternative Parents
Substituents
  • Alkylthiol
    • 

  • 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
logP0.84ALOGPS
logP0.98ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.81ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.92 m³·mol⁻¹ChemAxon
Polarizability10.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031707  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008370  
KNApSAcK IDNot Available
Chemspider ID13865015  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1,2-Ethanedithiol  
METLIN IDNot Available
PubChem Compound10902  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available