Showing metabocard for Bis(2-hydroxyethyl) trisulfide (MMDBc0018201)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 08:26:34 UTC
Update Date2025-10-07 16:06:48 UTC
Metabolite IDMMDBc0018201
Metabolite Identification
Common NameBis(2-hydroxyethyl) trisulfide
DescriptionBis(2-hydroxyethyl) trisulfide is a thiosulfate derivative that belongs to the class of organosulfur compounds. This metabolite has been shown to influence various biochemical pathways, particularly in immune response modulation. In studies involving J774A.1 cells, bis(2-hydroxyethyl) trisulfide has been reported to increase cytochrome b mRNA levels, indicating its potential role in mitochondrial function and oxidative stress responses (PMID:8799491 ). Furthermore, it has been demonstrated to activate mouse peritoneal macrophages, suggesting its involvement in the immune activation process (PMID:8287048 ). The cytotoxic effects of this compound, isolated from Bacillus stearothermophilus UK563, have been investigated in the context of mRNA expression levels in macrophages, highlighting its potential as a modulator of gene expression in immune cells (PMID:8799491 ). Overall, bis(2-hydroxyethyl) trisulfide appears to play a significant role in cellular signaling pathways related to immune responses and may serve as a valuable compound for further research in immunology and cellular metabolism.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x0000564323901a98>


  Mrv1533004241500382D          

  9  8  0  0  0  0            999 V2000
    2.9980    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000564323901a98>

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3D SDF for #<Metabolite:0x0000564323901a98>

  Mrv1533004241500382D          

  9  8  0  0  0  0            999 V2000
    2.9980    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0018201

> <DATABASE_NAME>
MIME

> <SMILES>
OCCSSSCCO

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O2S3/c5-1-3-7-9-8-4-2-6/h5-6H,1-4H2

> <INCHI_KEY>
PSTIDNOIODJAFC-UHFFFAOYSA-N

> <FORMULA>
C4H10O2S3

> <MOLECULAR_WEIGHT>
186.3

> <EXACT_MASS>
185.984293084

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
18.551829269637125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(2-hydroxyethyl)sulfanyl]disulfanyl}ethan-1-ol

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
0.05539878433333326

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.706151750773422

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.10381556290271

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6217205526829277

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
45.6528

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(2-hydroxyethyl)sulfanyl]disulfanyl}ethanol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x0000564323901a98>
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PDB for #<Metabolite:0x0000564323901a98>
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       5.596   4.771   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       9.597   4.001   0.000  0.00  0.00           S+0
HETATM    5  S   UNK     0      10.931   4.771   0.000  0.00  0.00           S+0
HETATM    6  S   UNK     0      12.265   4.001   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    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 #<Metabolite:0x0000564323901a98>
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SMILES for #<Metabolite:0x0000564323901a98>
OCCSSSCCO
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INCHI for #<Metabolite:0x0000564323901a98>
InChI=1S/C4H10O2S3/c5-1-3-7-9-8-4-2-6/h5-6H,1-4H2
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Synonyms
ValueSource
2-{[(2-hydroxyethyl)sulphanyl]disulphanyl}ethan-1-olGenerator
Bis(2-hydroxyethyl)trisulfideMeSH
BS-1 CompoundMeSH
Molecular FormulaC4H10O2S3
Average Mass186.3
Monoisotopic Mass185.984293084
IUPAC Name2-{[(2-hydroxyethyl)sulfanyl]disulfanyl}ethan-1-ol
Traditional Name2-{[(2-hydroxyethyl)sulfanyl]disulfanyl}ethanol
CAS Registry NumberNot Available
SMILES
OCCSSSCCO
InChI Identifier
InChI=1S/C4H10O2S3/c5-1-3-7-9-8-4-2-6/h5-6H,1-4H2
InChI KeyPSTIDNOIODJAFC-UHFFFAOYSA-N