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Showing NP-Card for Hydroxypyruvic acid (NP0055015)

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Record Information
Version2.0
Created at2022-04-28 01:11:16 UTC
Updated at2022-04-28 01:11:16 UTC
NP-MRD IDNP0055015
Secondary Accession NumbersNone
Natural Product Identification
Common NameHydroxypyruvic acid
DescriptionHydroxypyruvic acid, also known as 3-hydroxypyruvate or OH-pyr, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Hydroxypyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Hydroxypyruvic acid exists in all living organisms, ranging from bacteria to humans. Hydroxypyruvic acid and L-alanine can be biosynthesized from pyruvic acid and L-serine; which is mediated by the enzyme serine--pyruvate aminotransferase. In humans, hydroxypyruvic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Outside of the human body, Hydroxypyruvic acid has been detected, but not quantified in, several different foods, such as elderberries, summer savories, fireweeds, garland chrysanthemums, and shiitakes. Hydroxypyruvic acid is found in Eremosphaera viridis and Trypanosoma brucei. Hydroxypyruvic acid was first documented in 1946 (PMID: 20989501). This could make hydroxypyruvic acid a potential biomarker for the consumption of these foods (PMID: 972784) (PMID: 13163046) (PMID: 13328834) (PMID: 13522577) (PMID: 13522578) (PMID: 13564115).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0055015 (Hydroxypyruvic acid)


  Mrv1652307092016152D          

  7  6  0  0  0  0            999 V2000
    1.4291   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.0313    0.0000 O   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
  5  7  2  0  0  0  0
M  END
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3D MOL for NP0055015 (Hydroxypyruvic acid)

     RDKit          3D

 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.6391    1.2194   -0.7820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320    0.1478   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4554   -0.7091    0.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0737   -0.1921    0.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1036   -1.2627    0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0853    0.6858   -0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2760    0.1421    0.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2813   -1.7025    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9301    1.6513    0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1400    0.7837   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -0.7637    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  7 11  1  0
  6  9  1  0
  6 10  1  0
  3  8  1  0
M  END
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3D SDF for NP0055015 (Hydroxypyruvic acid)


  Mrv1652307092016152D          

  7  6  0  0  0  0            999 V2000
    1.4291   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.0313    0.0000 O   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
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0055015

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h4H,1H2,(H,6,7)

> <INCHI_KEY>
HHDDCCUIIUWNGJ-UHFFFAOYSA-N

> <FORMULA>
C3H4O4

> <MOLECULAR_WEIGHT>
104.0615

> <EXACT_MASS>
104.010958616

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
8.16699861049387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-2-oxopropanoic acid

> <ALOGPS_LOGP>
-1.43

> <JCHEM_LOGP>
-0.7513740926666667

> <ALOGPS_LOGS>
0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.009350701452298

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5681387148679744

> <JCHEM_PKA_STRONGEST_BASIC>
-3.393691120437987

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
19.6919

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxypyruvic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0055015 (Hydroxypyruvic acid)

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PDB for NP0055015 (Hydroxypyruvic acid)
HEADER    PROTEIN                                 09-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-20         0                                  
HETATM    1  O   UNK     0       2.668  -0.385   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -1.925   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334   0.385   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.668  -0.385   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.334   1.925   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0055015 (Hydroxypyruvic acid)
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SMILES for NP0055015 (Hydroxypyruvic acid)
OCC(=O)C(O)=O
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INCHI for NP0055015 (Hydroxypyruvic acid)
InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h4H,1H2,(H,6,7)
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View in JSmol
Synonyms
ValueSource
3-HydroxypyruvateKegg
3-Hydroxypyruvic acidKegg
HydroxypyruvateGenerator
3-Hydroxy-2-oxopropanoateHMDB
3-Hydroxy-2-oxopropanoic acidHMDB
beta-HydroxypyruvateHMDB
OH-PyrHMDB
OH-PyruvateHMDB
2-Oxo-3-hydroxypropanoic acidHMDB
2-Oxo-3-hydroxypropionic acidHMDB
3-Hydroxy-2-oxopropionic acidHMDB
Hydroxypyruvic acidHMDB
beta-Hydroxypyruvic acidHMDB
β-Hydroxypyruvic acidHMDB
Chemical FormulaC3H4O4
Average Mass104.0615 Da
Monoisotopic Mass104.01096 Da
IUPAC Name3-hydroxy-2-oxopropanoic acid
Traditional Namehydroxypyruvic acid
CAS Registry NumberNot Available
SMILES
OCC(=O)C(O)=O
InChI Identifier
InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h4H,1H2,(H,6,7)
InChI KeyHHDDCCUIIUWNGJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
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
Eremosphaera viridisViridiplantae
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
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassHydroxy acids and derivatives  
Sub ClassBeta hydroxy acids and derivatives  
Direct ParentBeta hydroxy acids and derivatives  
Alternative Parents
Substituents
  • Beta-hydroxy acid
    • 

  • Alpha-keto acid
    • 

  • Keto acid
    • 

  • Monosaccharide
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Primary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • 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-1.4ALOGPS
logP-0.75ChemAxon
logS0.3ALOGPS
pKa (Strongest Acidic)2.57ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.69 m³·mol⁻¹ChemAxon
Polarizability8.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001352  
DrugBank IDDB02951  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030913  
KNApSAcK IDC00007563  
Chemspider ID939  
KEGG Compound IDC00168  
BioCyc IDOH-PYR  
BiGG ID34120  
Wikipedia LinkHydroxypyruvic_acid  
METLIN ID482  
PubChem Compound964  
PDB IDNot Available
ChEBI ID30841  
Good Scents IDNot Available
References
General References
  1. Kolvraa S, Rasmussen K, Brandt NJ: D-glyceric acidemia: biohcemical studies of a new syndrome. Pediatr Res. 1976 Oct;10(10):825-30. doi: 10.1203/00006450-197610000-00003. [PubMed:972784  ] 
  2. STAFFORD HA, MAGALDI A, VENNESLAND B: The enzymatic reduction of hydroxypyruvic acid to D-glyceric acid in higher plants. J Biol Chem. 1954 Apr;207(2):621-9. [PubMed:13163046  ] 
  3. HOLZER H, GOEDDE HW, SCHNEIDER S: [Exchange of hydroxypyruvic acid and glycol aldehyde with carboxylase and alcohol dehydrogenase from yeast]. Biochem Z. 1955;327(4):245-54. [PubMed:13328834  ] 
  4. DICKENS F, WILLIAMSON DH: The preparation and properties of lithium hydroxypyruvate and hydroxypyruvic acid. Biochem J. 1958 Jan;68(1):74-81. doi: 10.1042/bj0680074. [PubMed:13522577  ] 
  5. BELLAMY LJ, WILLIAMS RL: The infrared spectra of hydroxypyruvic acid and related compounds. Biochem J. 1958 Jan;68(1):81-4. [PubMed:13522578  ] 
  6. WILLIAMSON DH: The preparation, estimation, and some properties of hydroxypyruvic acid. J Med Lab Technol. 1958 Jul;15(3):149-64. [PubMed:13564115  ] 
  7. BEHAL FJ: Hydroxypyruvic acid formation in Aspergillus niger. Arch Biochem Biophys. 1960 May;88:110-2. doi: 10.1016/0003-9861(60)90204-6. [PubMed:13798280  ] 
  8. SPRINSON DB, CHARGAFF E: The occurrence of hydroxypyruvic acid in biological systems. J Biol Chem. 1946 Jul;164:411-5. [PubMed:20989501  ]