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Showing metabocard for Succimer (HMDB0014706)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:43 UTC
HMDB IDHMDB0014706
Secondary Accession Numbers
  • HMDB14706
Metabolite Identification
Common NameSuccimer
DescriptionSuccimer is only found in individuals that have used or taken this drug. It is a mercaptodicarboxylic acid used as an antidote to heavy metal poisoning because it forms strong chelates with them. [PubChem]Succimer is a heavy metal chelator. It binds with high specificity to ions of lead in the blood to form a water-soluble complex that is subsequently excreted by the kidneys. Succimer can also chelate mercury, cadmium, and arsenic in this manner.
Structure
Data?1582753211
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014706 (Succimer)

566
  Mrv0541 02231214462D          

 10  9  0  0  1  0            999 V2000
    3.5217   -1.0312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    1.0312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5  9  2  0  0  0  0
  6 10  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for HMDB0014706 (Succimer)

HMDB0014706
     RDKit          3D
Succimer
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.7447   -0.8761   -1.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2297   -0.6831   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274   -1.3416   -0.2227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6861    0.1402    0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8926    1.4385    0.9945 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6665    0.7253    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7199    1.7956   -1.1169 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003   -0.3357    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6691   -0.3374    1.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321   -1.3782   -0.6048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5952   -1.8530    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6044   -0.4952    1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547    2.6638    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031    1.3802    1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    1.1137   -2.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248   -1.9569   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
 10 16  1  0
M  END
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3D SDF for HMDB0014706 (Succimer)

566
  Mrv0541 02231214462D          

 10  9  0  0  1  0            999 V2000
    3.5217   -1.0312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    1.0312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5  9  2  0  0  0  0
  6 10  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014706

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O4S2/c5-3(6)1(9)2(10)4(7)8/h1-2,9-10H,(H,5,6)(H,7,8)

> <INCHI_KEY>
ACTRVOBWPAIOHC-UHFFFAOYSA-N

> <FORMULA>
C4H6O4S2

> <MOLECULAR_WEIGHT>
182.218

> <EXACT_MASS>
181.97075006

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.4676630169322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-disulfanylbutanedioic acid

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
0.25882704599999995

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.44874638068228

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3712346491431497

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
38.46740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chemet

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0014706 (Succimer)

HMDB0014706
     RDKit          3D
Succimer
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.7447   -0.8761   -1.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2297   -0.6831   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274   -1.3416   -0.2227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6861    0.1402    0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8926    1.4385    0.9945 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6665    0.7253    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7199    1.7956   -1.1169 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003   -0.3357    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6691   -0.3374    1.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321   -1.3782   -0.6048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5952   -1.8530    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6044   -0.4952    1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547    2.6638    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031    1.3802    1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    1.1137   -2.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248   -1.9569   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
 10 16  1  0
M  END
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PDB for HMDB0014706 (Succimer)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 566                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.574  -1.925   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       7.907   1.925   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       3.907  -0.385   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.575   0.385   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.240   1.925   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.241  -1.925   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.574  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.907   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.240   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.241  -0.385   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5    9                                                            
CONECT    6   10                                                            
CONECT    7    1    8    9                                                  
CONECT    8    2    7   10                                                  
CONECT    9    3    5    7                                                  
CONECT   10    4    6    8                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0014706 (Succimer)

COMPND    HMDB0014706
HETATM    1  O1  UNL     1      -0.745  -0.876  -1.617  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.230  -0.683  -0.476  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.427  -1.342  -0.223  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.686   0.140   0.595  1.00  0.00           C  
HETATM    5  S1  UNL     1      -1.893   1.439   0.995  1.00  0.00           S  
HETATM    6  C3  UNL     1       0.667   0.725   0.327  1.00  0.00           C  
HETATM    7  S2  UNL     1       0.720   1.796  -1.117  1.00  0.00           S  
HETATM    8  C4  UNL     1       1.700  -0.336   0.306  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.669  -0.337   1.100  1.00  0.00           O  
HETATM   10  O4  UNL     1       1.632  -1.378  -0.605  1.00  0.00           O  
HETATM   11  H1  UNL     1      -2.595  -1.853   0.627  1.00  0.00           H  
HETATM   12  H2  UNL     1      -0.604  -0.495   1.508  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.355   2.664   0.525  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.903   1.380   1.210  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.819   1.114  -2.319  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.425  -1.957  -0.834  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    6   12
CONECT    5   13
CONECT    6    7    8   14
CONECT    7   15
CONECT    8    9    9   10
CONECT   10   16
END
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SMILES for HMDB0014706 (Succimer)

OC(=O)C(S)C(S)C(O)=O
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INCHI for HMDB0014706 (Succimer)

InChI=1S/C4H6O4S2/c5-3(6)1(9)2(10)4(7)8/h1-2,9-10H,(H,5,6)(H,7,8)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC4H6O4S2
Average Molecular Weight182.218
Monoisotopic Molecular Weight181.97075006
IUPAC Name2,3-disulfanylbutanedioic acid
Traditional Namechemet
CAS Registry Number304-55-2
SMILES
OC(=O)C(S)C(S)C(O)=O
InChI Identifier
InChI=1S/C4H6O4S2/c5-3(6)1(9)2(10)4(7)8/h1-2,9-10H,(H,5,6)(H,7,8)
InChI KeyACTRVOBWPAIOHC-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
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • 2-mercaptocarboxylic acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alkylthiol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point193 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.43 g/LNot Available
LogP-0.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00566 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00566 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 ID8988
KEGG Compound IDC07598
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimercaptosuccinic acid
METLIN IDNot Available
PubChem Compound9354
PDB IDNot Available
ChEBI ID140459
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. Mann KV, Travers JD: Succimer, an oral lead chelator. Clin Pharm. 1991 Dec;10(12):914-22. [PubMed:1663439 ]
  2. Aaseth J, Jacobsen D, Andersen O, Wickstrom E: Treatment of mercury and lead poisonings with dimercaptosuccinic acid and sodium dimercaptopropanesulfonate. A review. Analyst. 1995 Mar;120(3):853-4. [PubMed:7741240 ]
  3. Miller AL: Dimercaptosuccinic acid (DMSA), a non-toxic, water-soluble treatment for heavy metal toxicity. Altern Med Rev. 1998 Jun;3(3):199-207. [PubMed:9630737 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.