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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:37 UTC

HMDB ID

HMDB0001352

Secondary Accession Numbers

HMDB01352

Metabolite Identification

Common Name

Hydroxypyruvic acid

Description

Hydroxypyruvic 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. This could make hydroxypyruvic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Hydroxypyruvate	Kegg
3-Hydroxypyruvic acid	Kegg
Hydroxypyruvate	Generator
3-Hydroxy-2-oxopropanoate	HMDB
3-Hydroxy-2-oxopropanoic acid	HMDB
beta-Hydroxypyruvate	HMDB
OH-Pyr	HMDB
OH-Pyruvate	HMDB
2-Oxo-3-hydroxypropanoic acid	HMDB
2-Oxo-3-hydroxypropionic acid	HMDB
3-Hydroxy-2-oxopropionic acid	HMDB
Hydroxypyruvic acid	HMDB
beta-Hydroxypyruvic acid	HMDB
β-Hydroxypyruvic acid	HMDB

Chemical Formula

C₃H₄O₄

Average Molecular Weight

104.0615

Monoisotopic Molecular Weight

104.010958616

IUPAC Name

3-hydroxy-2-oxopropanoic acid

Traditional Name

hydroxypyruvic acid

CAS Registry Number

1113-60-6

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

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 )

Ontology

Physiological effect

Organoleptic effect

Taste

Sour

Odor

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001352)

Excreta

Biofluid or Excreta

Urine (PMID: 21388201)
Feces (PMID: 25037050)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001352)
Peroxisome (HMDB: HMDB0001352)

Source

Exogenous

Food

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Glycine and Serine Metabolism (HMDB: HMDB0001352)

Disease pathway

Dimethylglycine Dehydrogenase Deficiency (PathBank: SMP0000242)
Dihydropyrimidine Dehydrogenase Deficiency (DHPD) (PathBank: SMP0000179)
Sarcosinemia (PathBank: SMP0000244)
Non-Ketotic Hyperglycinemia (PathBank: SMP0000223)
Hyperglycinemia, Non-Ketotic (PathBank: SMP0000485)
3-Phosphoglycerate Dehydrogenase Deficiency (PathBank: SMP0000721)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	120.779	31661259
DarkChem	[M-H]-	113.031	31661259
AllCCS	[M+H]+	126.3	32859911
AllCCS	[M-H]-	119.456	32859911
DeepCCS	[M+H]+	125.617	30932474
DeepCCS	[M-H]-	122.819	30932474
DeepCCS	[M-2H]-	159.189	30932474
DeepCCS	[M+Na]+	133.748	30932474
AllCCS	[M+H]+	126.3	32859911
AllCCS	[M+H-H2O]+	122.0	32859911
AllCCS	[M+NH4]+	130.3	32859911
AllCCS	[M+Na]+	131.5	32859911
AllCCS	[M-H]-	119.5	32859911
AllCCS	[M+Na-2H]-	123.3	32859911
AllCCS	[M+HCOO]-	127.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxypyruvic acid	OCC(=O)C(O)=O	1771.3	Standard polar	33892256
Hydroxypyruvic acid	OCC(=O)C(O)=O	1448.8	Standard non polar	33892256
Hydroxypyruvic acid	OCC(=O)C(O)=O	951.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxypyruvic acid,1TMS,isomer #1	C[Si](C)(C)OCC(=O)C(=O)O	1143.6	Semi standard non polar	33892256
Hydroxypyruvic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(=O)CO	1064.0	Semi standard non polar	33892256
Hydroxypyruvic acid,1TMS,isomer #3	C[Si](C)(C)OC(=CO)C(=O)O	1201.0	Semi standard non polar	33892256
Hydroxypyruvic acid,2TMS,isomer #1	C[Si](C)(C)OCC(=O)C(=O)O[Si](C)(C)C	1292.9	Semi standard non polar	33892256
Hydroxypyruvic acid,2TMS,isomer #2	C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O	1315.1	Semi standard non polar	33892256
Hydroxypyruvic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(=CO)O[Si](C)(C)C	1228.3	Semi standard non polar	33892256
Hydroxypyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1396.4	Semi standard non polar	33892256
Hydroxypyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1305.1	Standard non polar	33892256
Hydroxypyruvic acid,3TMS,isomer #1	C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1352.9	Standard polar	33892256
Hydroxypyruvic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(=O)C(=O)O	1418.9	Semi standard non polar	33892256
Hydroxypyruvic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CO	1334.7	Semi standard non polar	33892256
Hydroxypyruvic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CO)C(=O)O	1434.3	Semi standard non polar	33892256
Hydroxypyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	1710.0	Semi standard non polar	33892256
Hydroxypyruvic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	1788.5	Semi standard non polar	33892256
Hydroxypyruvic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(=CO)O[Si](C)(C)C(C)(C)C	1730.1	Semi standard non polar	33892256
Hydroxypyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1999.0	Semi standard non polar	33892256
Hydroxypyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1886.9	Standard non polar	33892256
Hydroxypyruvic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1784.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Hydroxypyruvic acid GC-MS (1 MEOX; 2 TMS)	splash10-0iki-3910000000-c702dadd4b10b9c2e21c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxypyruvic acid GC-MS (1 MEOX; 2 TMS)	splash10-03ei-8930000000-6f1615bef5d93f87b361	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxypyruvic acid EI-B (Non-derivatized)	splash10-0gvk-1920000000-c10a7388ab610f99688d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxypyruvic acid EI-B (Non-derivatized)	splash10-03dj-1930000000-91df46c8a6c638ffe0f6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxypyruvic acid GC-EI-TOF (Non-derivatized)	splash10-03ds-2910000000-bc634dfde6ae74b517bf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxypyruvic acid GC-EI-TOF (Non-derivatized)	splash10-0gvt-2900000000-37fc3d3c38147e1d8cd8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxypyruvic acid GC-MS (Non-derivatized)	splash10-0iki-3910000000-c702dadd4b10b9c2e21c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxypyruvic acid GC-MS (Non-derivatized)	splash10-03ei-8930000000-6f1615bef5d93f87b361	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxypyruvic acid GC-EI-TOF (Non-derivatized)	splash10-03dj-1920000000-408d150435ee3edcc7d1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxypyruvic acid GC-EI-TOF (Non-derivatized)	splash10-0gvt-2900000000-fc662023f269ec21b82e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxypyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9000000000-b7c06a28c87e687f07a8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxypyruvic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00ac-9440000000-afd8c910b7b1f49d2e62	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxypyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxypyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxypyruvic acid 35V, Negative-QTOF	splash10-0a4i-9000000000-d1755e284e492b01243a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 10V, Positive-QTOF	splash10-0a4r-9600000000-12ab714e9a2767f1b0b5	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 20V, Positive-QTOF	splash10-0a4r-9100000000-c1a1da67ff71584bbd6a	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-cafdd074d8a05bebf155	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 10V, Negative-QTOF	splash10-0udi-7900000000-f2aeab79489832ab6fca	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 20V, Negative-QTOF	splash10-0pc0-9200000000-f62ce4a7bd46da93fc09	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-1f52435889596b02dbf5	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 10V, Negative-QTOF	splash10-0k96-9200000000-cd93a4168536c1a376db	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 20V, Negative-QTOF	splash10-0006-9000000000-3cb0c9f5ca761bc8f191	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 40V, Negative-QTOF	splash10-0006-9000000000-6ffb9541e24882de3fac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 10V, Positive-QTOF	splash10-052u-9100000000-697deb69236e2f95e74f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 20V, Positive-QTOF	splash10-052f-9000000000-ebcddbdd296882eee9ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxypyruvic acid 40V, Positive-QTOF	splash10-0006-9000000000-7c612a451346078594a2	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Mitochondria
Peroxisome

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Glycine, serine and threonine metabolism	Not Available
Dimethylglycine Dehydrogenase Deficiency		Not Available
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)		Not Available
Sarcosinemia		Not Available
Non Ketotic Hyperglycinemia		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	10.8 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21388201	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB02951

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30841

Food Biomarker Ontology

Not Available

VMH ID

HPYR

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

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)

General References

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 ]

Enzymes

Enzyme Details

1. Glyoxylate reductase/hydroxypyruvate reductase

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Enzyme with hydroxy-pyruvate reductase, glyoxylate reductase and D-glycerate dehydrogenase enzymatic activities. Reduces hydroxypyruvate to D-glycerate, glyoxylate to glycolate oxidizes D-glycerate to hydroxypyruvate.
Gene Name:: GRHPR
Uniprot ID:: Q9UBQ7
Molecular weight:: 35667.875

Reactions

Glyceric acid + NAD(P)(+) → Hydroxypyruvic acid + NAD(P)H	details
Glyceric acid + NAD → Hydroxypyruvic acid + NADH + Hydrogen Ion	details
Glyceric acid + NADP → Hydroxypyruvic acid + NADPH + Hydrogen Ion	details

Enzyme Details

2. Serine--pyruvate aminotransferase

General function:: Involved in metabolic process
Specific function:: Not Available
Gene Name:: AGXT
Uniprot ID:: P21549
Molecular weight:: 43009.535

Reactions

L-Serine + Pyruvic acid → Hydroxypyruvic acid + L-Alanine	details
L-Serine + Glyoxylic acid → Hydroxypyruvic acid + Glycine	details

Enzyme Details

3. Putative 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) (By similarity).
Gene Name:: HYI
Uniprot ID:: Q5T013
Molecular weight:: 30405.4

Reactions

Hydroxypyruvic acid → Tartronate semialdehyde	details

Showing metabocard for Hydroxypyruvic acid (HMDB0001352)

MOL for HMDB0001352 (Hydroxypyruvic acid)

3D MOL for HMDB0001352 (Hydroxypyruvic acid)

3D SDF for HMDB0001352 (Hydroxypyruvic acid)

3D-SDF for HMDB0001352 (Hydroxypyruvic acid)

PDB for HMDB0001352 (Hydroxypyruvic acid)

3D PDB for HMDB0001352 (Hydroxypyruvic acid)

SMILES for HMDB0001352 (Hydroxypyruvic acid)

INCHI for HMDB0001352 (Hydroxypyruvic acid)

Structure for HMDB0001352 (Hydroxypyruvic acid)

3D Structure for HMDB0001352 (Hydroxypyruvic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions