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Showing metabocard for Dimercaptosuccinic acid monomethyl ester (HMDB0254837)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 14:18:41 UTC
Update Date2021-09-26 23:09:08 UTC
HMDB IDHMDB0254837
Secondary Accession NumbersNone
Metabolite Identification
Common NameDimercaptosuccinic acid monomethyl ester
DescriptionDimercaptosuccinic acid monomethyl ester, also known as mome-dmsa, belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain. Based on a literature review a significant number of articles have been published on Dimercaptosuccinic acid monomethyl ester. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dimercaptosuccinic acid monomethyl ester is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dimercaptosuccinic acid monomethyl ester 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 HMDB0254837 (Dimercaptosuccinic acid monomethyl ester)

  Mrv1652309112116182D          

 11 10  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 S   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
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3D MOL for HMDB0254837 (Dimercaptosuccinic acid monomethyl ester)

HMDB0254837
     RDKit          3D
Dimercaptosuccinic acid monomethyl ester
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.0582    0.2107    0.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    0.1606   -0.2100 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -0.1477    0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3695   -0.3965    1.1961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1086   -0.1718   -1.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0907    1.4750   -1.9150 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5234   -0.5662   -0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3991   -2.2450   -0.0622 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1391    0.3377    0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357   -0.0782    1.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889    1.6726   -0.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8257    0.9927    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181    0.4475    1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837   -0.7579    0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273   -0.8731   -1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0571    1.5574   -2.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1649   -0.5875   -1.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345   -3.0669   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620    2.0363   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
 11 19  1  0
M  END
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3D SDF for HMDB0254837 (Dimercaptosuccinic acid monomethyl ester)

  Mrv1652309112116182D          

 11 10  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 S   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254837

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C(S)C(S)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O4S2/c1-9-5(8)3(11)2(10)4(6)7/h2-3,10-11H,1H3,(H,6,7)

> <INCHI_KEY>
GELAOSIUBCMYGY-UHFFFAOYSA-N

> <FORMULA>
C5H8O4S2

> <MOLECULAR_WEIGHT>
196.24

> <EXACT_MASS>
195.986401086

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
17.715583434005445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methoxy-4-oxo-2,3-disulfanylbutanoic acid

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.4047211019999999

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.953505342071654

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8111047112589866

> <JCHEM_PKA_STRONGEST_BASIC>
-7.2018552362776465

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
43.2365

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-4-oxo-2,3-disulfanylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0254837 (Dimercaptosuccinic acid monomethyl ester)

HMDB0254837
     RDKit          3D
Dimercaptosuccinic acid monomethyl ester
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.0582    0.2107    0.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    0.1606   -0.2100 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -0.1477    0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3695   -0.3965    1.1961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1086   -0.1718   -1.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0907    1.4750   -1.9150 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5234   -0.5662   -0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3991   -2.2450   -0.0622 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1391    0.3377    0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357   -0.0782    1.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889    1.6726   -0.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8257    0.9927    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181    0.4475    1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837   -0.7579    0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273   -0.8731   -1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0571    1.5574   -2.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1649   -0.5875   -1.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345   -3.0669   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620    2.0363   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
 11 19  1  0
M  END
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PDB for HMDB0254837 (Dimercaptosuccinic acid monomethyl ester)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.620   2.667   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
HETATM   10  S   UNK     0       8.621   4.977   0.000  0.00  0.00           S+0
HETATM   11  S   UNK     0       7.287   1.127   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11    5                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0254837 (Dimercaptosuccinic acid monomethyl ester)

COMPND    HMDB0254837
HETATM    1  C1  UNL     1       3.058   0.211   0.834  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.122   0.161  -0.210  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.785  -0.148   0.015  1.00  0.00           C  
HETATM    4  O2  UNL     1       0.369  -0.396   1.196  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.109  -0.172  -1.154  1.00  0.00           C  
HETATM    6  S1  UNL     1      -0.091   1.475  -1.915  1.00  0.00           S  
HETATM    7  C4  UNL     1      -1.523  -0.566  -0.791  1.00  0.00           C  
HETATM    8  S2  UNL     1      -1.399  -2.245  -0.062  1.00  0.00           S  
HETATM    9  C5  UNL     1      -2.139   0.338   0.180  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.536  -0.078   1.290  1.00  0.00           O  
HETATM   11  O4  UNL     1      -2.289   1.673  -0.126  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.826   0.993   0.579  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.618   0.448   1.816  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.584  -0.758   0.946  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.327  -0.873  -1.893  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.057   1.557  -2.726  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.165  -0.587  -1.695  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.434  -3.067  -0.524  1.00  0.00           H  
HETATM   19  H8  UNL     1      -3.062   2.036  -0.686  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    7   15
CONECT    6   16
CONECT    7    8    9   17
CONECT    8   18
CONECT    9   10   10   11
CONECT   11   19
END
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SMILES for HMDB0254837 (Dimercaptosuccinic acid monomethyl ester)

COC(=O)C(S)C(S)C(O)=O
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INCHI for HMDB0254837 (Dimercaptosuccinic acid monomethyl ester)

InChI=1S/C5H8O4S2/c1-9-5(8)3(11)2(10)4(6)7/h2-3,10-11H,1H3,(H,6,7)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Dimercaptosuccinate monomethyl esterGenerator
MoMe-dmsaMeSH
Dimercaptosuccinic acid monomethyl ester, (r*,r*)-(+-)-isomerMeSH
Dimercaptosuccinic acid monomethyl ester, lead saltMeSH
Chemical FormulaC5H8O4S2
Average Molecular Weight196.24
Monoisotopic Molecular Weight195.986401086
IUPAC Name4-methoxy-4-oxo-2,3-disulfanylbutanoic acid
Traditional Name4-methoxy-4-oxo-2,3-disulfanylbutanoic acid
CAS Registry NumberNot Available
SMILES
COC(=O)C(S)C(S)C(O)=O
InChI Identifier
InChI=1S/C5H8O4S2/c1-9-5(8)3(11)2(10)4(6)7/h2-3,10-11H,1H3,(H,6,7)
InChI KeyGELAOSIUBCMYGY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentThia fatty acids
Alternative Parents
Substituents
  • Fatty acid ester
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • 2-mercaptocarboxylic acid
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alkylthiol
  • Organosulfur compound
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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 ID9610394
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11435530
PDB IDNot Available
ChEBI IDNot Available
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 ]