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Showing metabocard for 3-Sulfinylpyruvic acid (HMDB0001405)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:40 UTC
HMDB IDHMDB0001405
Secondary Accession Numbers
  • HMDB0002332
  • HMDB01405
  • HMDB02332
Metabolite Identification
Common Name3-Sulfinylpyruvic acid
Description3-Sulfinylpyruvic acid is a compound found in the mammalian cysteine metabolic pathway. It is the deaminated form of cysteine sulfinic acid which subsequently spontaneously reacts to form pyruvate and release sulfur dioxide (PMID: 3925121 , 6822523 ). It is the byproduct of oxidoreductases (EC 1.4.1.-), and aspartate transaminase (EC 2.6.1.1). It is also often associated with hepatic disease, and the presence of aspartate transaminase is used in diagnostic biochemical assays of such ailments (PMID: 17310554 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001405 (3-Sulfinylpyruvic acid)

  Mrv1652306121920132D          

  9  8  0  0  0  0            999 V2000
 9993.2233 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9374 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6531 9993.3504    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6531 9992.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3686 9993.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5086 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7936 9993.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5086 9994.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.2233 9992.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  2  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
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for HMDB0001405 (3-Sulfinylpyruvic acid)

HMDB0001405
     RDKit          3D
3-Sulfinylpyruvic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
    0.1079   -0.3309    1.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0762   -0.2791    0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3471   -0.1525    1.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9166   -0.3448   -0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695   -0.3010   -1.2954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703   -0.4592   -1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7999   -0.4528   -0.2195 S   0  0  0  0  0  4  0  0  0  0  0  0
   -1.8891   -1.7174    0.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080    0.9649    0.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -0.5141    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4167    0.4226   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3995   -1.3962   -1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7677    1.0876    1.0892 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
  6 11  1  0
  6 12  1  0
  9 13  1  0
M  END
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3D SDF for HMDB0001405 (3-Sulfinylpyruvic acid)

  Mrv1652306121920132D          

  9  8  0  0  0  0            999 V2000
 9993.2233 9993.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9374 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6531 9993.3504    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6531 9992.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3686 9993.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5086 9993.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7936 9993.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5086 9994.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.2233 9992.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  2  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
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001405

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H4O5S/c4-2(3(5)6)1-9(7)8/h1H2,(H,5,6)(H,7,8)

> <INCHI_KEY>
JXYLQEMXCAAMOL-UHFFFAOYSA-N

> <FORMULA>
C3H4O5S

> <MOLECULAR_WEIGHT>
152.126

> <EXACT_MASS>
151.977943928

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
11.626876761768395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxo-3-sulfinopropanoic acid

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-0.3367

> <ALOGPS_LOGS>
-1.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.4980979499885008

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7113654556517908

> <JCHEM_PKA_STRONGEST_BASIC>
-9.87426248852735

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
26.890599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-sulfinylpyruvate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001405 (3-Sulfinylpyruvic acid)

HMDB0001405
     RDKit          3D
3-Sulfinylpyruvic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
    0.1079   -0.3309    1.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0762   -0.2791    0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3471   -0.1525    1.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9166   -0.3448   -0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695   -0.3010   -1.2954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703   -0.4592   -1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7999   -0.4528   -0.2195 S   0  0  0  0  0  4  0  0  0  0  0  0
   -1.8891   -1.7174    0.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080    0.9649    0.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -0.5141    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4167    0.4226   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3995   -1.3962   -1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7677    1.0876    1.0892 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
  6 11  1  0
  6 12  1  0
  9 13  1  0
M  END
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PDB for HMDB0001405 (3-Sulfinylpyruvic acid)

HEADER    PROTEIN                                 12-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-JUN-19         0                                  
HETATM    1  C   UNK     0    8654.0178654.254   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8655.3508655.023   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0    8656.6868654.254   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0    8656.6868652.713   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8658.0218655.023   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8652.6838655.023   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8651.3488654.254   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8652.6838656.563   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8654.0178652.713   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0001405 (3-Sulfinylpyruvic acid)

COMPND    HMDB0001405
HETATM    1  O1  UNL     1       0.108  -0.331   1.667  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.076  -0.279   0.875  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.347  -0.152   1.437  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.917  -0.345  -0.568  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.969  -0.301  -1.295  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.370  -0.459  -1.257  1.00  0.00           C  
HETATM    7  S1  UNL     1      -1.800  -0.453  -0.219  1.00  0.00           S  
HETATM    8  O4  UNL     1      -1.889  -1.717   0.577  1.00  0.00           O  
HETATM    9  O5  UNL     1      -1.908   0.965   0.660  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.134  -0.514   0.881  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.417   0.423  -1.966  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.400  -1.396  -1.881  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.768   1.088   1.089  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    5    6
CONECT    6    7   11   12
CONECT    7    8    8    9
CONECT    9   13
END
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SMILES for HMDB0001405 (3-Sulfinylpyruvic acid)

OC(=O)C(=O)CS(O)=O
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INCHI for HMDB0001405 (3-Sulfinylpyruvic acid)

InChI=1S/C3H4O5S/c4-2(3(5)6)1-9(7)8/h1H2,(H,5,6)(H,7,8)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC3H4O5S
Average Molecular Weight152.126
Monoisotopic Molecular Weight151.977943928
IUPAC Name2-oxo-3-sulfinopropanoic acid
Traditional Name3-sulfinylpyruvate
CAS Registry Number88947-38-0
SMILES
OC(=O)C(=O)CS(O)=O
InChI Identifier
InChI=1S/C3H4O5S/c4-2(3(5)6)1-9(7)8/h1H2,(H,5,6)(H,7,8)
InChI KeyJXYLQEMXCAAMOL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassAlpha-keto acids and derivatives
Direct ParentAlpha-keto acids and derivatives
Alternative Parents
Substituents
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Sulfinic acid
  • Ketone
  • Alkanesulfinic acid
  • Alkanesulfinic acid or derivatives
  • Sulfinic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
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 Locations
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022965
KNApSAcK IDNot Available
Chemspider ID108
KEGG Compound IDC05527
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6627
PubChem Compound110
PDB IDNot Available
ChEBI ID1665
Food Biomarker OntologyNot Available
VMH ID3SNPYR
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChatagner, Fernande; Bergeret, Bernadette; Fromageot, Claude. Transaminations taking part in the metabolism of cysteinesulfinic acid in mammals. Ann. Acad. Sci. Fennicae (1955), II;No.60(Ser. A), 393-400.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Griffith OW: Cysteinesulfinate metabolism. altered partitioning between transamination and decarboxylation following administration of beta-methyleneaspartate. J Biol Chem. 1983 Feb 10;258(3):1591-8. [PubMed:6822523 ]
  2. Kunert J: Metabolism of sulfur-containing amino acids in the dermatophyte Microsporum gypseum. II. Acidic amino acid derivatives. J Basic Microbiol. 1985;25(2):111-8. [PubMed:3925121 ]
  3. Oparinde DP, Oghagbon EK, Okesina AB, Olatunji PO, Ojuawo AO: Role of hepatic enzymes in the biochemical assessment of the severity of sickle cell anemia. Trop Gastroenterol. 2006 Jul-Sep;27(3):118-21. [PubMed:17310554 ]

Enzymes

Enzyme Details
1. Aspartate aminotransferase, cytoplasmic
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
Reactions
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + Glutamic aciddetails
Enzyme Details
2. Aspartate aminotransferase, mitochondrial
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + Glutamic aciddetails