ECMDB: Hydroxypyruvic acid (ECMDB01352) (M2MDB000351)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (601)

Record Information

Version

2.0

Creation Date

2012-05-31 13:50:37 -0600

Update Date

2015-09-13 12:56:11 -0600

Secondary Accession Numbers

ECMDB01352

Identification

Name:

Hydroxypyruvic acid

Description

Hydroxypyruvic acid is an intermediate in the metabolism of Glycine, serine and threonine. It is a substrate for Serine--pyruvate aminotransferase and Glyoxylate reductase/hydroxypyruvate reductase.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

β-hydroxypyruvate
β-hydroxypyruvic acid
3-Hydroxy-2-oxopropanoate
3-Hydroxy-2-oxopropanoic acid
3-Hydroxypyruvate
3-Hydroxypyruvic acid
b-Hydroxypyruvate
b-Hydroxypyruvic acid
Beta-Hydroxypyruvate
Beta-Hydroxypyruvic acid
Hydroxypyruvate
OH-pyr
OH-pyruvate
OH-pyruvic acid
β-Hydroxypyruvate
β-Hydroxypyruvic acid

Chemical Formula:

C₃H₄O₄

Weight:

Average: 104.0615
Monoisotopic: 104.010958616

InChI Key:

HHDDCCUIIUWNGJ-UHFFFAOYSA-N

InChI:

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

CAS number:

1113-60-6

IUPAC Name:

3-hydroxy-2-oxopropanoic acid

Traditional IUPAC Name:

hydroxypyruvic acid

SMILES:

OCC(=O)C(O)=O

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta 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 Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:30841 )
3-hydroxy monocarboxylic acid (CHEBI:30841 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	209 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-0.75	ChemAxon
logS	0.3	ALOGPS
pKa (Strongest Acidic)	2.57	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	19.69 m³·mol⁻¹	ChemAxon
Polarizability	8.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Hydrogen ion + Hydroxypyruvic acid + NADH > Glyceric acid + NAD
Hydrogen ion + Hydroxypyruvic acid + NADPH > Glyceric acid + NADP
Hydroxypyruvic acid <> Tartronate semialdehyde
Glyceric acid + NAD <> Hydroxypyruvic acid + NADH + Hydrogen ion
Glyceric acid + NADP <> Hydroxypyruvic acid + NADPH + Hydrogen ion
Phosphohydroxypyruvic acid + Water > Hydroxypyruvic acid + Phosphate
Glyceric acid + NAD(P)(+) > Hydroxypyruvic acid + NAD(P)H
Hydroxypyruvic acid > Tartronate semialdehyde
Hydroxypyruvic acid <> Tartronate semialdehyde
Hydrogen ion + Hydroxypyruvic acid + NADH > Glyceric acid + NAD
Hydroxypyruvic acid <> Tartronate semialdehyde

SMPDB Pathways:

Not Available

KEGG Pathways:

Glycine, serine and threonine metabolism ec00260
Glyoxylate and dicarboxylate metabolism ec00630
Metabolic pathways eco01100
Methane metabolism ec00680
Microbial metabolism in diverse environments ec01120

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-0iki-3910000000-c702dadd4b10b9c2e21c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-03ei-8930000000-6f1615bef5d93f87b361	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0gvk-1920000000-c10a7388ab610f99688d	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dj-1930000000-91df46c8a6c638ffe0f6	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03ds-2910000000-bc634dfde6ae74b517bf	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gvt-2900000000-37fc3d3c38147e1d8cd8	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0iki-3910000000-c702dadd4b10b9c2e21c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03ei-8930000000-6f1615bef5d93f87b361	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03dj-1920000000-408d150435ee3edcc7d1	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gvt-2900000000-fc662023f269ec21b82e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9000000000-b7c06a28c87e687f07a8	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00ac-9440000000-afd8c910b7b1f49d2e62	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-9000000000-d1755e284e492b01243a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-9600000000-12ab714e9a2767f1b0b5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-c1a1da67ff71584bbd6a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-cafdd074d8a05bebf155	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-7900000000-f2aeab79489832ab6fca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pc0-9200000000-f62ce4a7bd46da93fc09	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-1f52435889596b02dbf5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0k96-9200000000-cd93a4168536c1a376db	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-3cb0c9f5ca761bc8f191	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-6ffb9541e24882de3fac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052u-9100000000-697deb69236e2f95e74f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-ebcddbdd296882eee9ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-7c612a451346078594a2	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Kolvraa S, Rasmussen K, Brandt NJ: D-glyceric acidemia: biohcemical studies of a new syndrome. Pediatr Res. 1976 Oct;10(10):825-30. Pubmed: 972784
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Behal, Francis J. Hydroxypyruvic acid formation in Aspergillus niger. Archives of Biochemistry and Biophysics (1960), 88 110-12.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	30841
HMDB ID	HMDB01352
Pubchem Compound ID	964
Kegg ID	C00168
ChemSpider ID	939
Wikipedia ID	Hydroxypyruvic_acid
BioCyc ID	OH-PYR
EcoCyc ID	OH-PYR
Ligand Expo	3PY

Enzymes

Protein Details

1. Hydroxypyruvate isomerase

General function:: Carbohydrate transport and metabolism
Specific function:: Catalyzes the reversible isomerization between hydroxypyruvate and 2-hydroxy-3-oxopropanoate (also termed tartronate semialdehyde)
Gene Name:: hyi
Uniprot ID:: P30147
Molecular weight:: 29377

Reactions

Hydroxypyruvate = 2-hydroxy-3-oxopropanoate.

Protein Details

2. Glyoxylate/hydroxypyruvate reductase B

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Can also reduce 2,5-diketo-D-gluconate (25DKG) to 5-keto-D- gluconate (5KDG), 2-keto-D-gluconate (2KDG) to D-gluconate, and 2- keto-L-gulonate (2KLG) to L-idonate (IA), but it is not its physiological function. Inactive towards 2-oxoglutarate, oxaloacetate, pyruvate, 5-keto-D-gluconate, D-fructose and L- sorbose. Activity with NAD is very low
Gene Name:: ghrB
Uniprot ID:: P37666
Molecular weight:: 35395

Reactions

Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.
D-gluconate + NADP(+) = 2-dehydro-D-gluconate + NADPH.

Protein Details

3. Uncharacterized Nudix hydrolase nudL

General function:: Involved in hydrolase activity
Specific function:: Probably mediates the hydrolysis of some nucleoside diphosphate derivatives
Gene Name:: nudL
Uniprot ID:: P43337
Molecular weight:: 21435

Protein Details

4. Glyoxylate/hydroxypyruvate reductase A

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Inactive towards 2-oxo-D-gluconate, 2-oxoglutarate, oxaloacetate and pyruvate. Only D- and L-glycerate are involved in the oxidative activity with NADP. Activity with NAD is very low
Gene Name:: ghrA
Uniprot ID:: P75913
Molecular weight:: 35343

Reactions

Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.

Hydroxypyruvic acid (ECMDB01352) (M2MDB000351)

Structure for #<Compound:0xae9196c4>

Enzymes

Reactions

Reactions

Reactions