Np mrd loader

Showing NP-Card for 3-Mercaptopyruvic acid (NP0001378)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:59:05 UTC
NP-MRD IDNP0001378
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Mercaptopyruvic acid
Description3-Mercaptopyruvic acid, also known as 3-mercapto-2-oxopropanoate or beta-thiopyruvate, 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. 3-Mercaptopyruvic acid is an intermediate in cysteine metabolism. 3-Mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 3-mercaptopyruvic acid participates in a number of enzymatic reactions. In particular, 3-mercaptopyruvic acid and cyanide can be converted into pyruvic acid and thiocyanate; which is mediated by the enzyme 3-mercaptopyruvate sulfurtransferase. In addition, 3-mercaptopyruvic acid can be biosynthesized from 3-mercaptolactic acid; which is mediated by the enzyme L-lactate dehydrogenase. It has been studied as a potential treatment for cyanide poisoning, but its half-life is too short for it to be clinically effective. In humans, 3-mercaptopyruvic acid is involved in cystinosis, ocular nonnephropathic. Outside of the human body, 3-mercaptopyruvic acid has been detected, but not quantified in several different foods, such as lima beans, spinachs, shallots, mexican groundcherries, and white lupines. This could make 3-mercaptopyruvic acid a potential biomarker for the consumption of these foods.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001378 (3-Mercaptopyruvic acid)


  Mrv1652305261923572D          

  7  6  0  0  0  0            999 V2000
   -0.1025    0.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8162   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1025    1.0021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112   -1.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287    0.1785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336    0.1785    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
M  END
Download

3D MOL for NP0001378 (3-Mercaptopyruvic acid)

HMDB0001368
     RDKit          3D
3-Mercaptopyruvic acid
 11 10  0  0  0  0  0  0  0  0999 V2000
   -0.5415    1.0408   -1.4531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1701    0.4444   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230    0.6505   -0.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3816   -0.4741    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9821   -1.0791    1.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -0.7345    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7814    0.1947   -1.2594 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938    1.4923    0.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -1.8238   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5588   -0.5477    1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    0.8364   -0.7700 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
  3  8  1  0
  6  9  1  0
  6 10  1  0
  7 11  1  0
M  END
Download

3D SDF for NP0001378 (3-Mercaptopyruvic acid)


  Mrv1652305261923572D          

  7  6  0  0  0  0            999 V2000
   -0.1025    0.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8162   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1025    1.0021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112   -1.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287    0.1785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336    0.1785    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001378

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)

> <INCHI_KEY>
OJOLFAIGOXZBCI-UHFFFAOYSA-N

> <FORMULA>
C3H4O3S

> <MOLECULAR_WEIGHT>
120.127

> <EXACT_MASS>
119.988114684

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
10.147025919940411

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.15

> <JCHEM_LOGP>
0.29243937466666664

> <ALOGPS_LOGS>
-1.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.607725794599306

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9127072837959105

> <JCHEM_PKA_STRONGEST_BASIC>
-9.88372855258473

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
25.818900000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-mercaptopyruvic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001378 (3-Mercaptopyruvic acid)

HMDB0001368
     RDKit          3D
3-Mercaptopyruvic acid
 11 10  0  0  0  0  0  0  0  0999 V2000
   -0.5415    1.0408   -1.4531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1701    0.4444   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230    0.6505   -0.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3816   -0.4741    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9821   -1.0791    1.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -0.7345    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7814    0.1947   -1.2594 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938    1.4923    0.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -1.8238   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5588   -0.5477    1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    0.8364   -0.7700 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
  3  8  1  0
  6  9  1  0
  6 10  1  0
  7 11  1  0
M  END
Download

PDB for NP0001378 (3-Mercaptopyruvic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.191   0.333   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.141  -0.439   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.524  -0.439   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.191   1.871   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.141  -1.984   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.480   0.333   0.000  0.00  0.00           O+0
HETATM    7  S   UNK     0      -2.863   0.333   0.000  0.00  0.00           S+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
Download

3D PDB for NP0001378 (3-Mercaptopyruvic acid)

COMPND    HMDB0001368
HETATM    1  O1  UNL     1      -0.541   1.041  -1.453  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.170   0.444  -0.534  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.523   0.650  -0.309  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.382  -0.474   0.275  1.00  0.00           C  
HETATM    5  O3  UNL     1      -0.982  -1.079   1.194  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.049  -0.734   0.087  1.00  0.00           C  
HETATM    7  S1  UNL     1       1.781   0.195  -1.259  1.00  0.00           S  
HETATM    8  H1  UNL     1      -2.894   1.492   0.116  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.167  -1.824  -0.130  1.00  0.00           H  
HETATM   10  H3  UNL     1       1.559  -0.548   1.063  1.00  0.00           H  
HETATM   11  H4  UNL     1       2.936   0.836  -0.770  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    8
CONECT    4    5    5    6
CONECT    6    7    9   10
CONECT    7   11
END
Download

SMILES for NP0001378 (3-Mercaptopyruvic acid)

OC(=O)C(=O)CS
Download

INCHI for NP0001378 (3-Mercaptopyruvic acid)

InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)
Download
View in JSmol
Synonyms
ValueSource
3-Mercapto-2-oxopropanoic acidChEBI
3-MercaptopyruvateChEBI
MercaptopyruvateChEBI
2-oxo-3-SulfanylpropanoateKegg
3-Mercapto-2-oxopropanoateGenerator
Mercaptopyruvic acidGenerator
2-oxo-3-Sulfanylpropanoic acidGenerator
2-oxo-3-SulphanylpropanoateGenerator
2-oxo-3-Sulphanylpropanoic acidGenerator
3-Mercapto-pyruvateHMDB
3-Mercapto-pyruvic acidHMDB
beta-3-Mercapto-2-oxo-propanoateHMDB
beta-3-Mercapto-2-oxo-propanoic acidHMDB
beta-MercaptopyruvateHMDB
beta-Mercaptopyruvic acidHMDB
beta-ThiopyruvateHMDB
beta-Thiopyruvic acidHMDB
ThiopyruvateHMDB
3-Mercaptopyruvate monosodium saltHMDB
Chemical FormulaC3H4O3S
Average Mass120.1270 Da
Monoisotopic Mass119.98811 Da
IUPAC Name2-oxo-3-sulfanylpropanoic acid
Traditional Nameβ-mercaptopyruvic acid
CAS Registry Number2464-23-5
SMILES
OC(=O)C(=O)CS
InChI Identifier
InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)
InChI KeyOJOLFAIGOXZBCI-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaKNApSAcK Database
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
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
  • Ketone
  • Monocarboxylic acid or derivatives
  • 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 Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point97.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point253.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.834 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility9.09 g/LALOGPS
logP0.15ALOGPS
logP0.29ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.82 m³·mol⁻¹ChemAxon
Polarizability10.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001368
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030434
KNApSAcK IDC00007464
Chemspider ID96
KEGG Compound IDC00957
BioCyc ID3-MERCAPTO-PYRUVATE
BiGG ID36476
Wikipedia Link3-Mercaptopyruvic_acid
METLIN ID6195
PubChem Compound98
PDB IDNot Available
ChEBI ID16208
Good Scents IDrw1465131
References
General References
  1. Cooper AJ, Haber MT, Meister A: On the chemistry and biochemistry of 3-mercaptopyruvic acid, the alpha-keto acid analog of cysteine. J Biol Chem. 1982 Jan 25;257(2):816-26. [PubMed:7054184 ]
  2. Galardon E, Lec JC: Synthesis, Characterisation and Reactivity of 3-Mercaptopyruvic Acid. Chembiochem. 2018 May 20. doi: 10.1002/cbic.201800199. [PubMed:29779240 ]
  3. Andreessen C, Gerlt V, Steinbuchel A: Conversion of cysteine to 3-mercaptopyruvic acid by bacterial aminotransferases. Enzyme Microb Technol. 2017 Apr;99:38-48. doi: 10.1016/j.enzmictec.2017.01.004. Epub 2017 Jan 16. [PubMed:28193330 ]