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Showing metabocard for Phosphohydroxypyruvic acid (HMDB0001024)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:24 UTC
HMDB IDHMDB0001024
Secondary Accession Numbers
  • HMDB0060175
  • HMDB01024
  • HMDB60175
Metabolite Identification
Common NamePhosphohydroxypyruvic acid
DescriptionPhosphohydroxypyruvic acid, also known as 3-phosphooxypyruvate or hydroxypyruvic acid phosphate, belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position. Phosphohydroxypyruvic acid is a moderately acidic compound (based on its pKa). Phosphohydroxypyruvic acid exists in all living species, ranging from bacteria to humans. Within humans, phosphohydroxypyruvic acid participates in a number of enzymatic reactions. In particular, phosphohydroxypyruvic acid can be biosynthesized from 3-phosphoglyceric acid through the action of the enzyme D-3-phosphoglycerate dehydrogenase. In addition, phosphohydroxypyruvic acid and L-glutamic acid can be converted into phosphoserine and oxoglutaric acid through its interaction with the enzyme phosphoserine aminotransferase. In humans, phosphohydroxypyruvic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. A carboxyalkyl phosphate that is pyruvic acid substituted at position 3 by a 3-phosphonooxy group.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001024 (Phosphohydroxypyruvic acid)

  Mrv1652309042000172D          

 11 10  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  2  0  0  0  0
 10  1  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  2  0  0  0  0
 11 10  1  0  0  0  0
M  END
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3D MOL for HMDB0001024 (Phosphohydroxypyruvic acid)

HMDB0001024
     RDKit          3D
Phosphohydroxypyruvic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.0928   -0.5447   -1.7358 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900    0.0591   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8114    0.3960   -0.6168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5461    0.3889    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9551    0.9997    1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042    0.0583    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2736   -0.6084   -0.8796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9415   -0.9059   -0.7673 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.2618   -2.3131   -1.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    0.1736   -1.6990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747   -0.7752    0.8329 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0632    1.3773   -0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519    1.0279    0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2403   -0.5210    1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617    1.0882   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8218    0.0993    1.0638 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  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
  3 12  1  0
  6 13  1  0
  6 14  1  0
 10 15  1  0
 11 16  1  0
M  END
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3D SDF for HMDB0001024 (Phosphohydroxypyruvic acid)

  Mrv1652309042000172D          

 11 10  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  2  0  0  0  0
 10  1  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  2  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001024

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)

> <INCHI_KEY>
LFLUCDOSQPJJBE-UHFFFAOYSA-N

> <FORMULA>
C3H5O7P

> <MOLECULAR_WEIGHT>
184.0414

> <EXACT_MASS>
183.977289026

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.689006616785997

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxo-3-(phosphonooxy)propanoic acid

> <ALOGPS_LOGP>
-1.75

> <JCHEM_LOGP>
-0.8749401239999998

> <ALOGPS_LOGS>
-1.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.771821818294329

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0202501691523165

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
30.564799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosphohydroxypyruvate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001024 (Phosphohydroxypyruvic acid)

HMDB0001024
     RDKit          3D
Phosphohydroxypyruvic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.0928   -0.5447   -1.7358 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900    0.0591   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8114    0.3960   -0.6168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5461    0.3889    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9551    0.9997    1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042    0.0583    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2736   -0.6084   -0.8796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9415   -0.9059   -0.7673 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.2618   -2.3131   -1.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    0.1736   -1.6990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747   -0.7752    0.8329 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0632    1.3773   -0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519    1.0279    0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2403   -0.5210    1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617    1.0882   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8218    0.0993    1.0638 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  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
  3 12  1  0
  6 13  1  0
  6 14  1  0
 10 15  1  0
 11 16  1  0
M  END
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PDB for HMDB0001024 (Phosphohydroxypyruvic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.620   0.000   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.160  -2.667   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.850  -4.001   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.540   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
CONECT    1    2   10                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2    5    6                                                  
CONECT    4    2                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7   11                                                            
CONECT    8   11                                                            
CONECT    9   11                                                            
CONECT   10    1   11                                                       
CONECT   11    7    8    9   10                                             
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0001024 (Phosphohydroxypyruvic acid)

COMPND    HMDB0001024
HETATM    1  O1  UNL     1       2.093  -0.545  -1.736  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.490   0.059  -0.725  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.811   0.396  -0.617  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.546   0.389   0.308  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.955   1.000   1.327  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.104   0.058   0.262  1.00  0.00           C  
HETATM    7  O4  UNL     1      -0.274  -0.608  -0.880  1.00  0.00           O  
HETATM    8  P1  UNL     1      -1.941  -0.906  -0.767  1.00  0.00           P  
HETATM    9  O5  UNL     1      -2.262  -2.313  -1.227  1.00  0.00           O  
HETATM   10  O6  UNL     1      -2.836   0.174  -1.699  1.00  0.00           O  
HETATM   11  O7  UNL     1      -2.475  -0.775   0.833  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.063   1.377  -0.628  1.00  0.00           H  
HETATM   13  H2  UNL     1      -0.452   1.028   0.291  1.00  0.00           H  
HETATM   14  H3  UNL     1      -0.240  -0.521   1.134  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.762   1.088  -1.365  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.822   0.099   1.064  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5    6
CONECT    6    7   13   14
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   10   15
CONECT   11   16
END
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SMILES for HMDB0001024 (Phosphohydroxypyruvic acid)

OC(=O)C(=O)COP(O)(O)=O
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INCHI for HMDB0001024 (Phosphohydroxypyruvic acid)

InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-Phosphohydroxypyruvic acidChEBI
Hydroxypyruvic acid phosphateChEBI
3-Phosphonooxypyruvic acidKegg
3-PhosphohydroxypyruvateKegg
3-PhosphooxypyruvateKegg
Hydroxypyruvate phosphateGenerator
Hydroxypyruvic acid phosphoric acidGenerator
3-PhosphonooxypyruvateGenerator
3-Phosphooxypyruvic acidGenerator
PhosphohydroxypyruvateGenerator
2-oxo-3-(Phosphonooxy)-propanoateHMDB
2-oxo-3-(Phosphonooxy)-propanoic acidHMDB
3-PhosphonatooxypyruvateHMDB
2-Oxo-3-(phosphonooxy)propanoic acidHMDB
2-Oxo-3-(phosphonooxy)propionic acidHMDB
Phosphohydroxypyruvic acidHMDB
Chemical FormulaC3H5O7P
Average Molecular Weight184.0414
Monoisotopic Molecular Weight183.977289026
IUPAC Name2-oxo-3-(phosphonooxy)propanoic acid
Traditional Namephosphohydroxypyruvate
CAS Registry Number3913-50-6
SMILES
OC(=O)C(=O)COP(O)(O)=O
InChI Identifier
InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)
InChI KeyLFLUCDOSQPJJBE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentGlycerone phosphates
Alternative Parents
Substituents
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • 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
  • Cytoplasm (predicted from logP)
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 IDFDB022377
KNApSAcK IDC00019657
Chemspider ID103
KEGG Compound IDC03232
BioCyc ID3-P-HYDROXYPYRUVATE
BiGG ID41453
Wikipedia LinkPhosphohydroxypyruvic acid
METLIN ID484
PubChem Compound105
PDB IDNot Available
ChEBI ID30933
Food Biomarker OntologyNot Available
VMH ID3PHP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhao G, Winkler ME: A novel alpha-ketoglutarate reductase activity of the serA-encoded 3-phosphoglycerate dehydrogenase of Escherichia coli K-12 and its possible implications for human 2-hydroxyglutaric aciduria. J Bacteriol. 1996 Jan;178(1):232-9. [PubMed:8550422 ]
  2. Achouri Y, Rider MH, Schaftingen EV, Robbi M: Cloning, sequencing and expression of rat liver 3-phosphoglycerate dehydrogenase. Biochem J. 1997 Apr 15;323 ( Pt 2):365-70. [PubMed:9163325 ]
  3. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Enzymes

Enzyme Details
1. Phosphoserine aminotransferase
General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine (By similarity).
Gene Name:
PSAT1
Uniprot ID:
Q9Y617
Molecular weight:
35188.305
Reactions
Phosphoserine + Oxoglutaric acid → Phosphohydroxypyruvic acid + Glutamic aciddetails
Enzyme Details
2. D-3-phosphoglycerate dehydrogenase
General function:
Involved in phosphoglycerate dehydrogenase activity
Specific function:
Not Available
Gene Name:
PHGDH
Uniprot ID:
O43175
Molecular weight:
56650.03
Reactions
3-Phosphoglyceric acid + NAD → Phosphohydroxypyruvic acid + NADHdetails
3-Phosphoglyceric acid + NAD → Phosphohydroxypyruvic acid + NADH + Hydrogen Iondetails