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Showing NP-Card for Sulfopyruvate (NP0050508)

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Record Information
Version2.0
Created at2022-04-27 21:46:30 UTC
Updated at2022-04-27 21:46:30 UTC
NP-MRD IDNP0050508
Secondary Accession NumbersNone
Natural Product Identification
Common NameSulfopyruvate
Description3-Sulfopyruvic acid, also known as 3-sulfopyruvate, 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. A carboxyalkanesulfonic acid comprising pyruvic acid with a sulfo group attached at the C-3 position. 3-Sulfopyruvic acid is an extremely strong acidic compound (based on its pKa). 3-Sulfopyruvic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 3-Sulfopyruvic acid has been detected, but not quantified in, several different foods, such as yautia, nanking cherries, cloves, acerola, and strawberries. Sulfopyruvate is found in Methanobacterium formicicum and Methanosarcina strain TM-1. Sulfopyruvate was first documented in 1988 (PMID: 3346220). This could make 3-sulfopyruvic acid a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050508 (Sulfopyruvate)


  Mrv0541 02231216002D          

 10  9  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  2  0  0  0  0
M  END
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3D MOL for NP0050508 (Sulfopyruvate)

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3D SDF for NP0050508 (Sulfopyruvate)

  Mrv0541 02231216002D          

 10  9  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050508

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H4O6S/c4-2(3(5)6)1-10(7,8)9/h1H2,(H,5,6)(H,7,8,9)

> <INCHI_KEY>
BUTHMSUEBYPMKJ-UHFFFAOYSA-N

> <FORMULA>
C3H4O6S

> <MOLECULAR_WEIGHT>
168.125

> <EXACT_MASS>
167.97285855

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
12.462901413194915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.54

> <JCHEM_LOGP>
-0.7366029399999999

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.061448891817898

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.7581956511875605

> <JCHEM_POLAR_SURFACE_AREA>
108.73999999999998

> <JCHEM_REFRACTIVITY>
28.3335

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfopyruvate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050508 (Sulfopyruvate)
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PDB for NP0050508 (Sulfopyruvate)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.357  -1.334   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.976  -3.644   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.310   0.206   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       4.977  -1.334   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0       6.311  -0.564   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.747  -2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.207   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0050508 (Sulfopyruvate)
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SMILES for NP0050508 (Sulfopyruvate)
OC(=O)C(=O)CS(O)(=O)=O
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INCHI for NP0050508 (Sulfopyruvate)
InChI=1S/C3H4O6S/c4-2(3(5)6)1-10(7,8)9/h1H2,(H,5,6)(H,7,8,9)
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Synonyms
ValueSource
2-Carboxy-2-oxoethanesulfonic acidChEBI
3-SulfopyruvateChEBI
beta-Sulfopyruvic acidChEBI
SULFopyruvATEChEBI
2-Carboxy-2-oxoethanesulfonateGenerator
2-Carboxy-2-oxoethanesulphonateGenerator
2-Carboxy-2-oxoethanesulphonic acidGenerator
3-SulphopyruvateGenerator
3-Sulphopyruvic acidGenerator
b-SulfopyruvateGenerator
b-Sulfopyruvic acidGenerator
b-SulphopyruvateGenerator
b-Sulphopyruvic acidGenerator
beta-SulfopyruvateGenerator
beta-SulphopyruvateGenerator
beta-Sulphopyruvic acidGenerator
Β-sulfopyruvateGenerator
Β-sulfopyruvic acidGenerator
Β-sulphopyruvateGenerator
Β-sulphopyruvic acidGenerator
Sulfopyruvic acidGenerator
SulphopyruvateGenerator
Sulphopyruvic acidGenerator
2-oxo-3-SulfO-propanoateHMDB
2-oxo-3-SulfO-propanoic acidHMDB
2-oxo-3-SulfopropanoateHMDB
2-oxo-3-Sulfopropanoic acidHMDB
3-SulfonatopyruvateHMDB
Chemical FormulaC3H4O6S
Average Mass168.1250 Da
Monoisotopic Mass167.97286 Da
IUPAC Name2-oxo-3-sulfopropanoic acid
Traditional Namesulfopyruvate
CAS Registry NumberNot Available
SMILES
OC(=O)C(=O)CS(O)(=O)=O
InChI Identifier
InChI=1S/C3H4O6S/c4-2(3(5)6)1-10(7,8)9/h1H2,(H,5,6)(H,7,8,9)
InChI KeyBUTHMSUEBYPMKJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Methanobacterium formicicumEuryarchaeota
Methanosarcina strain TM-1Euryarchaeota
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
    • 

  • Alkanesulfonic acid
    • 

  • Sulfonyl
    • 

  • Organosulfonic acid
    • 

  • Organosulfonic acid or derivatives
    • 

  • Organic sulfonic acid or derivatives
    • 

  • Ketone
    • 

  • 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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.5ALOGPS
logP-0.74ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area108.74 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.33 m³·mol⁻¹ChemAxon
Polarizability12.46 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004045  
DrugBank IDDB02156  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030464  
KNApSAcK IDC00000764  
Chemspider ID389590  
KEGG Compound IDC05528  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440717  
PDB IDNot Available
ChEBI ID16894  
Good Scents IDNot Available
References
General References
  1. Weinstein CL, Griffith OW: Cysteinesulfonate and beta-sulfopyruvate metabolism. Partitioning between decarboxylation, transamination, and reduction pathways. J Biol Chem. 1988 Mar 15;263(8):3735-43. [PubMed:3346220  ]