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Showing metabocard for 2,3-Dimercapto-1-propanesulfonic acid (HMDB0251547)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:54:43 UTC
Update Date2021-10-01 21:21:55 UTC
HMDB IDHMDB0251547
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,3-Dimercapto-1-propanesulfonic acid
Description2,3-disulfanylpropane-1-sulfonic acid, also known as DMPS or 2,3-dimercaptopropane-1-sulfonate, belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom). 2,3-disulfanylpropane-1-sulfonic acid is an extremely strong acidic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,3-dimercapto-1-propanesulfonic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,3-Dimercapto-1-propanesulfonic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0251547 (2,3-Dimercapto-1-propanesulfonic acid)

  Mrv1652306031608572D          

  9  8  0  0  0  0            999 V2000
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    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
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  7  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  2  0  0  0  0
M  END
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3D MOL for HMDB0251547 (2,3-Dimercapto-1-propanesulfonic acid)

HMDB0251547
     RDKit          3D
2,3-Dimercapto-1-propanesulfonic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.5925    1.5908   -1.6364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140    0.6618   -0.5574 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.1347    1.2703    0.2413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5510   -0.7745   -1.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949    0.3134    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -0.3673   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1681    0.6437   -1.4110 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5455   -0.5344    0.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0218   -1.3389    0.3230 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -1.4457   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    1.2277    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1181   -0.3848    1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305   -1.3620   -0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169    1.8998   -0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7628    0.5036    1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658   -1.1540    1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4223   -0.7495   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0251547 (2,3-Dimercapto-1-propanesulfonic acid)

  Mrv1652306031608572D          

  9  8  0  0  0  0            999 V2000
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    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
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  7  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251547

> <DATABASE_NAME>
hmdb

> <SMILES>
OS(=O)(=O)CC(S)CS

> <INCHI_IDENTIFIER>
InChI=1S/C3H8O3S3/c4-9(5,6)2-3(8)1-7/h3,7-8H,1-2H2,(H,4,5,6)

> <INCHI_KEY>
JLVSRWOIZZXQAD-UHFFFAOYSA-N

> <FORMULA>
C3H8O3S3

> <MOLECULAR_WEIGHT>
188.27

> <EXACT_MASS>
187.96355764

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
17.05157695690801

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-disulfanylpropane-1-sulfonic acid

> <ALOGPS_LOGP>
-0.21

> <JCHEM_LOGP>
-0.0778724006666667

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.678301672917888

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.9190506893202306

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
41.30270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DMPS

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0251547 (2,3-Dimercapto-1-propanesulfonic acid)

HMDB0251547
     RDKit          3D
2,3-Dimercapto-1-propanesulfonic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.5925    1.5908   -1.6364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140    0.6618   -0.5574 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.1347    1.2703    0.2413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5510   -0.7745   -1.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949    0.3134    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -0.3673   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1681    0.6437   -1.4110 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5455   -0.5344    0.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0218   -1.3389    0.3230 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -1.4457   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    1.2277    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1181   -0.3848    1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305   -1.3620   -0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169    1.8998   -0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7628    0.5036    1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658   -1.1540    1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4223   -0.7495   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0251547 (2,3-Dimercapto-1-propanesulfonic acid)

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.540   0.000   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM    7  S   UNK     0       2.667  -4.620   0.000  0.00  0.00           S+0
HETATM    8  S   UNK     0       2.667  -1.540   0.000  0.00  0.00           S+0
HETATM    9  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    3    7                                                       
CONECT    2    3    9                                                       
CONECT    3    1    2    8                                                  
CONECT    4    9                                                            
CONECT    5    9                                                            
CONECT    6    9                                                            
CONECT    7    1                                                            
CONECT    8    3                                                            
CONECT    9    2    4    5    6                                             
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0251547 (2,3-Dimercapto-1-propanesulfonic acid)

COMPND    HMDB0251547
HETATM    1  O1  UNL     1      -1.593   1.591  -1.636  1.00  0.00           O  
HETATM    2  S1  UNL     1      -2.014   0.662  -0.557  1.00  0.00           S  
HETATM    3  O2  UNL     1      -3.135   1.270   0.241  1.00  0.00           O  
HETATM    4  O3  UNL     1      -2.551  -0.774  -1.226  1.00  0.00           O  
HETATM    5  C1  UNL     1      -0.695   0.313   0.590  1.00  0.00           C  
HETATM    6  C2  UNL     1       0.470  -0.367  -0.096  1.00  0.00           C  
HETATM    7  S2  UNL     1       1.168   0.644  -1.411  1.00  0.00           S  
HETATM    8  C3  UNL     1       1.546  -0.534   0.978  1.00  0.00           C  
HETATM    9  S3  UNL     1       3.022  -1.339   0.323  1.00  0.00           S  
HETATM   10  H1  UNL     1      -2.754  -1.446  -0.518  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.345   1.228   1.089  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.118  -0.385   1.343  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.231  -1.362  -0.467  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.517   1.900  -0.900  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.763   0.504   1.334  1.00  0.00           H  
HETATM   16  H7  UNL     1       1.066  -1.154   1.775  1.00  0.00           H  
HETATM   17  H8  UNL     1       3.422  -0.750  -0.862  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    4   10
CONECT    5    6   11   12
CONECT    6    7    8   13
CONECT    7   14
CONECT    8    9   15   16
CONECT    9   17
END
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SMILES for HMDB0251547 (2,3-Dimercapto-1-propanesulfonic acid)

OS(=O)(=O)CC(S)CS
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INCHI for HMDB0251547 (2,3-Dimercapto-1-propanesulfonic acid)

InChI=1S/C3H8O3S3/c4-9(5,6)2-3(8)1-7/h3,7-8H,1-2H2,(H,4,5,6)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC3H8O3S3
Average Molecular Weight188.27
Monoisotopic Molecular Weight187.96355764
IUPAC Name2,3-disulfanylpropane-1-sulfonic acid
Traditional NameDMPS
CAS Registry NumberNot Available
SMILES
OS(=O)(=O)CC(S)CS
InChI Identifier
InChI=1S/C3H8O3S3/c4-9(5,6)2-3(8)1-7/h3,7-8H,1-2H2,(H,4,5,6)
InChI KeyJLVSRWOIZZXQAD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
Substituents
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • Alkylthiol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC10922
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6321
PDB IDNot Available
ChEBI ID888
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details
1. Solute carrier family 22 member 6
General function:
Not Available
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of cidofovir, adefovir, 9-(2-phosphonylmethoxyethyl) guanine (PMEG), 9-(2-phosphonylmethoxyethyl) diaminopurine (PMEDAP), ochratoxin (OTA), acyclovir (ACV), 3'-azido-3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS), 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF) and edaravone sulfate (By similarity). Mediates the sodium-independent uptake of p-aminohippurate (PAH) and 2,3-dimercapto-1-propanesulfonic acid (DMPS). PAH uptake is inhibited by p-chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), indomethacin, sulindac, diclofenac, carprofen, okadaic acid, furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, bumetamide, losartan, probenecid, phenol red and glutarate (By similarity). PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), urate, alpha-ketoglutarate and probenecid.
Gene Name:
SLC22A6
Uniprot ID:
Q9TSY7
Molecular weight:
60588.3
Enzyme Details
2. Solute carrier family 22 member 6
General function:
Not Available
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS), 9-(2-phosphonylmethoxyethyl) guanine (PMEG), 9-(2-phosphonylmethoxyethyl) diaminopurine (PMEDAP), ochratoxin (OTA), acyclovir (ACV), 3'-azido-3-'deoxythymidine (AZT), cimetidine (CMD) and edaravone sulfate. Mediates the sodium-independent uptake of p-aminohippurate (PAH), cidofovir, adefovir, 2,4-dichloro-phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF). PAH uptake is inhibited by p-chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), indomethacin, sulindac, diclofenac, carprofen, okadaic acid, benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, bumetamide, losartan, phenol red, urate and alpha-ketoglutarate (By similarity). PAH uptake is inhibited by glutarate and probenecid.
Gene Name:
SLC22A6
Uniprot ID:
O35956
Molecular weight:
60765.66

Transporters

Enzyme Details
1. Solute carrier family 22 member 6
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8