T3DB: Pyruvic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (16)XML

Targets (16)

Record Information

Version

2.0

Creation Date

2014-08-29 06:27:15 UTC

Update Date

2014-12-24 20:26:46 UTC

Accession Number

T3D4325

Identification

Common Name

Pyruvic acid

Class

Small Molecule

Description

Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes.

Compound Type

Animal Toxin
Dietary Supplement
Drug
Food Toxin
Metabolite
Micronutrient
Natural Compound
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
2-ketopropionic acid
2-Oxopropanoate
2-Oxopropanoic acid
2-Oxopropansaeure
2-Oxopropionate
2-Oxopropionic acid
2-Oxopropionsaeure
a-Ketopropionate
a-Ketopropionic acid
Acetylformate
Acetylformic acid
Acide pyruvique
alpha-Ketopropionate
alpha-Ketopropionic acid
alpha-Oxopropionsaeure
Brenztraubensaeure
BTS
CH3COCOOH
Pyroracemate
Pyroracemic acid
Pyruvate
α-ketopropionic acid

Chemical Formula

C₃H₄O₃

Average Molecular Mass

88.062 g/mol

Monoisotopic Mass

88.016 g/mol

CAS Registry Number

127-17-3

IUPAC Name

2-oxopropanoic acid

Traditional Name

pyruvic acid

SMILES

CC(=O)C(O)=O

InChI Identifier

InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)

InChI Key

InChIKey=LCTONWCANYUPML-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Alpha-keto acids and derivatives

Direct Parent

Alpha-keto acids and derivatives

Alternative Parents

Substituents

Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:32816 )
Oxo fatty acids (LMFA01060077 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Peroxisome

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Brain
Fibroblasts
Kidney
Liver
Muscle
Myocardium
Neuron
Pancreas
Skeletal Muscle
Spleen
Testes
Thyroid Gland

Pathways

Name	SMPDB Link	KEGG Link
Alanine Metabolism	SMP00055	map00250
Amino Sugar Metabolism	SMP00045	map00520
Ammonia Recycling	SMP00009	map00910
Citric Acid Cycle	SMP00057	map00020
Cysteine Metabolism	SMP00013	map00270
Gluconeogenesis	SMP00128	Not Available
Glucose-Alanine Cycle	SMP00127	Not Available
Glycine and Serine Metabolism	SMP00004	map00260
Glycolysis	SMP00040	Not Available
Pyruvaldehyde Degradation	SMP00459	Not Available
Pyruvate Metabolism	SMP00060	map00620
Transfer of Acetyl Groups into Mitochondria	SMP00466	Not Available
Urea Cycle	SMP00059	Not Available
Congenital lactic acidosis	SMP00546	Not Available
Pyruvate Carboxylase Deficiency	SMP00350	Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)	SMP00334	Not Available
Pyruvate Dehydrogenase Complex Deficiency	SMP00212	Not Available
Pyruvate dehydrogenase deficiency (E3)	SMP00550	Not Available

Applications

Not Available

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	13.8°C
Boiling Point	54°C at 1.00E+01 mm Hg
Solubility	1E+006 mg/L (at 20°C)
LogP	-0.5

Predicted Properties

Property	Value	Source
Water Solubility	134 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	0.066	ChemAxon
logS	0.18	ALOGPS
pKa (Strongest Acidic)	2.93	ChemAxon
pKa (Strongest Basic)	-9.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	17.99 m³·mol⁻¹	ChemAxon
Polarizability	7.31 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00dr-4900000000-f26ef76666e40ab9fe61	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-00di-5900000000-b8e81f82572d4796e944	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-5970000000-154bf9ad168a12593fcc	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-a2cf85a5e1d2379d26df	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-4900000000-f26ef76666e40ab9fe61	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-5900000000-b8e81f82572d4796e944	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-5970000000-154bf9ad168a12593fcc	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-5900000000-5b1f470d4ff91420618c	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-5417b44aa241a7ba27e8	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dm-9400000000-6db65a709bdc47e3adf7	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-a2cf85a5e1d2379d26df	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-dd49835da8355fb6e625	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-f09d8e3d7a774b255d89	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-7d91f6f626cab1a366fd	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-8ae98cdb3e142034e52a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-e04e6c68013983e1b6dc	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-dd49835da8355fb6e625	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-f09d8e3d7a774b255d89	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-7d91f6f626cab1a366fd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-8ae98cdb3e142034e52a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-e04e6c68013983e1b6dc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000f-9000000000-f24c93ecfd3928827154	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0udj-9000000000-fc3b9ad0c57f44261fba	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-f3444f8b94ee5a0a9f74	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-0avr-9000000000-dc40a6a1b9b166d6e68a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-016r-9000000000-efac7b176bb77118ecb8	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-d0defa72b09503c6d6d1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9000000000-c25fa150e9c490319a2a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ccb42b4c05ddd001990f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-faf36ff70d6205370270	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-60c1a02aabf80f51050f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-ca5f4a2f06787d8b62a0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-0eb1fb2cdd24bdc78601	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-87bbaed151efac084591	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-87bbaed151efac084591	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-f315d0752893e7d0c657	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Toxicity Profile

Route of Exposure

Pyruvate is absorbed from the gastrointestinal tract from whence it is transported to the liver via the portal circulation.

Mechanism of Toxicity

Pyruvate serves as a biological fuel by being converted to acetyl coenzyme A, which enters the tricarboxylic acid or Krebs cycle where it is metabolized to produce ATP aerobically. Energy can also be obtained anaerobically from pyruvate via its conversion to lactate. Pyruvate injections or perfusions increase contractile function of hearts when metabolizing glucose or fatty acids. This inotropic effect is striking in hearts stunned by ischemia/reperfusion. The inotropic effect of pyruvate requires intracoronary infusion. Among possible mechanisms for this effect are increased generation of ATP and an increase in ATP phosphorylation potential. Another is activation of pyruvate dehydrogenase, promoting its own oxidation by inhibiting pyruvate dehydrogenase kinase. Pyruvate dehydrogenase is inactivated in ischemia myocardium. Yet another is reduction of cytosolic inorganic phosphate concentration. Pyruvate, as an antioxidant, is known to scavenge such reactive oxygen species as hydrogen peroxide and lipid peroxides. Indirectly, supraphysiological levels of pyruvate may increase cellular reduced glutathione.

Metabolism

In the liver, pyruvate is metabolized via several pathways.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For nutritional supplementation, also for treating dietary shortage or imbalance

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

32816

BioCyc ID

PYRUVATE

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

PYR

ACToR ID

Not Available

Wikipedia Link

Pyruvic_acid

References

Synthesis Reference

Tadamitsu Kiyoura, “Process for producing salts of pyruvic acid.” U.S. Patent US4242525, issued December, 1965.

MSDS

Link

General References

Nielsen J, Ytrebo LM, Borud O: Lactate and pyruvate concentrations in capillary blood from newborns. Acta Paediatr. 1994 Sep;83(9):920-2. [7819686 ]
Ka T, Yamamoto T, Moriwaki Y, Kaya M, Tsujita J, Takahashi S, Tsutsumi Z, Fukuchi M, Hada T: Effect of exercise and beer on the plasma concentration and urinary excretion of purine bases. J Rheumatol. 2003 May;30(5):1036-42. [12734903 ]
Talseth T, Haegele KD, McNay JL, Skrdlant HB, Clementi WA, Shepherd AM: Pharmacokinetics and cardiovascular effects in rabbits of a major hydralazine metabolite, the hydralazine pyruvic-acid hydrazone. J Pharmacol Exp Ther. 1979 Dec;211(3):509-13. [512915 ]
Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. [15627241 ]
Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [8579834 ]
Reece PA, Cozamanis I, Zacest R: Selective high-performance liquid chromatographic assays for hydralazine and its metabolites in plasma of man. J Chromatogr. 1980 Mar 14;181(3-4):427-40. [7391156 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
Meijer-Severs GJ, Van Santen E, Meijer BC: Short-chain fatty acid and organic acid concentrations in feces of healthy human volunteers and their correlations with anaerobe cultural counts during systemic ceftriaxone administration. Scand J Gastroenterol. 1990 Jul;25(7):698-704. [2396083 ]
Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [12097436 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [15882454 ]
Elling D, Bader K: [Biochemical changes in cervix mucus in stepwise malignant transformation of cervix epithelium]. Zentralbl Gynakol. 1990;112(9):555-60. [2378186 ]
Mongan PD, Capacchione J, West S, Karaian J, Dubois D, Keneally R, Sharma P: Pyruvate improves redox status and decreases indicators of hepatic apoptosis during hemorrhagic shock in swine. Am J Physiol Heart Circ Physiol. 2002 Oct;283(4):H1634-44. Epub 2002 Jun 20. [12234818 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [8412012 ]
Foster KJ, Alberti KG, Hinks L, Lloyd B, Postle A, Smythe P, Turnell DC, Walton R: Blood intermediary metabolite and insulin concentrations after an overnight fast: reference ranges for adults, and interrelations. Clin Chem. 1978 Sep;24(9):1568-72. [688619 ]
Tsuchiya H, Hashizume I, Tokunaga T, Tatsumi M, Takagi N, Hayashi T: High-performance liquid chromatography of alpha-keto acids in human saliva. Arch Oral Biol. 1983;28(11):989-92. [6581765 ]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Monocarboxylate transporter 1

General Function:: Symporter activity
Specific Function:: Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. Depending on the tissue and on cicumstances, mediates the import or export of lactic acid and ketone bodies. Required for normal nutrient assimilation, increase of white adipose tissue and body weight gain when on a high-fat diet. Plays a role in cellular responses to a high-fat diet by modulating the cellular levels of lactate and pyruvate, small molecules that contribute to the regulation of central metabolic pathways and insulin secretion, with concomitant effects on plasma insulin levels and blood glucose homeostasis.
Gene Name:: SLC16A1
Uniprot ID:: P53985
Molecular Weight:: 53943.685 Da

References

Duerr JM, Tucker K: Pyruvate transport in isolated cardiac mitochondria from two species of amphibian exhibiting dissimilar aerobic scope: Bufo marinus and Rana catesbeiana. J Exp Zool A Ecol Genet Physiol. 2007 Aug 1;307(8):425-38. [17583564 ]
Han M, Trotta P, Coleman C, Linask KK: MCT-4, A511/Basigin and EF5 expression patterns during early chick cardiomyogenesis indicate cardiac cell differentiation occurs in a hypoxic environment. Dev Dyn. 2006 Jan;235(1):124-31. [16110503 ]
Shimoyama Y, Akihara Y, Kirat D, Iwano H, Hirayama K, Kagawa Y, Ohmachi T, Matsuda K, Okamoto M, Kadosawa T, Yokota H, Taniyama H: Expression of monocarboxylate transporter 1 in oral and ocular canine melanocytic tumors. Vet Pathol. 2007 Jul;44(4):449-57. [17606506 ]
Shimada A, Nakagawa Y, Morishige H, Yamamoto A, Fujita T: Functional characteristics of H+ -dependent nicotinate transport in primary cultures of astrocytes from rat cerebral cortex. Neurosci Lett. 2006 Jan 16;392(3):207-12. Epub 2005 Oct 5. [16213084 ]
Philp A, Macdonald AL, Watt PW: Lactate--a signal coordinating cell and systemic function. J Exp Biol. 2005 Dec;208(Pt 24):4561-75. [16326938 ]

Target Details

2. Monocarboxylate transporter 2

General Function:: Symporter activity
Specific Function:: Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. Functions as high-affinity pyruvate transporter.
Gene Name:: SLC16A7
Uniprot ID:: O60669
Molecular Weight:: 52199.745 Da

References

Bonen A, Heynen M, Hatta H: Distribution of monocarboxylate transporters MCT1-MCT8 in rat tissues and human skeletal muscle. Appl Physiol Nutr Metab. 2006 Feb;31(1):31-9. [16604139 ]
Hinoi E, Takarada T, Tsuchihashi Y, Fujimori S, Moriguchi N, Wang L, Uno K, Yoneda Y: A molecular mechanism of pyruvate protection against cytotoxicity of reactive oxygen species in osteoblasts. Mol Pharmacol. 2006 Sep;70(3):925-35. Epub 2006 Jun 9. [16766717 ]
Yoshida Y, Holloway GP, Ljubicic V, Hatta H, Spriet LL, Hood DA, Bonen A: Negligible direct lactate oxidation in subsarcolemmal and intermyofibrillar mitochondria obtained from red and white rat skeletal muscle. J Physiol. 2007 Aug 1;582(Pt 3):1317-35. Epub 2007 Jun 7. [17556391 ]
de Laplanche E, Gouget K, Cleris G, Dragounoff F, Demont J, Morales A, Bezin L, Godinot C, Perriere G, Mouchiroud D, Simonnet H: Physiological oxygenation status is required for fully differentiated phenotype in kidney cortex proximal tubules. Am J Physiol Renal Physiol. 2006 Oct;291(4):F750-60. Epub 2006 Apr 4. [16597615 ]
Pierre K, Pellerin L: Monocarboxylate transporters in the central nervous system: distribution, regulation and function. J Neurochem. 2005 Jul;94(1):1-14. [15953344 ]

Target Details

3. Monocarboxylate transporter 5

General Function:: Symporter activity
Specific Function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate (By similarity).
Gene Name:: SLC16A4
Uniprot ID:: O15374
Molecular Weight:: 54021.43 Da

References

Kay HH, Zhu S, Tsoi S: Hypoxia and lactate production in trophoblast cells. Placenta. 2007 Aug-Sep;28(8-9):854-60. Epub 2007 Feb 2. [17275903 ]
Han M, Trotta P, Coleman C, Linask KK: MCT-4, A511/Basigin and EF5 expression patterns during early chick cardiomyogenesis indicate cardiac cell differentiation occurs in a hypoxic environment. Dev Dyn. 2006 Jan;235(1):124-31. [16110503 ]
Bonen A, Heynen M, Hatta H: Distribution of monocarboxylate transporters MCT1-MCT8 in rat tissues and human skeletal muscle. Appl Physiol Nutr Metab. 2006 Feb;31(1):31-9. [16604139 ]
Pierre K, Pellerin L: Monocarboxylate transporters in the central nervous system: distribution, regulation and function. J Neurochem. 2005 Jul;94(1):1-14. [15953344 ]
Shimada A, Nakagawa Y, Morishige H, Yamamoto A, Fujita T: Functional characteristics of H+ -dependent nicotinate transport in primary cultures of astrocytes from rat cerebral cortex. Neurosci Lett. 2006 Jan 16;392(3):207-12. Epub 2005 Oct 5. [16213084 ]

Target Details

4. Pyruvate carboxylase, mitochondrial

General Function:: Pyruvate carboxylase activity
Specific Function:: Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
Gene Name:: PC
Uniprot ID:: P11498
Molecular Weight:: 129632.565 Da

References

Jitrapakdee S, Vidal-Puig A, Wallace JC: Anaplerotic roles of pyruvate carboxylase in mammalian tissues. Cell Mol Life Sci. 2006 Apr;63(7-8):843-54. [16505973 ]
Simpson NE, Khokhlova N, Oca-Cossio JA, Constantinidis I: Insights into the role of anaplerosis in insulin secretion: A 13C NMR study. Diabetologia. 2006 Jun;49(6):1338-48. Epub 2006 Mar 31. [16575559 ]
Jensen MV, Joseph JW, Ilkayeva O, Burgess S, Lu D, Ronnebaum SM, Odegaard M, Becker TC, Sherry AD, Newgard CB: Compensatory responses to pyruvate carboxylase suppression in islet beta-cells. Preservation of glucose-stimulated insulin secretion. J Biol Chem. 2006 Aug 4;281(31):22342-51. Epub 2006 Jun 1. [16740637 ]
Ikeda K, Yukihiro Hiraoka B, Iwai H, Matsumoto T, Mineki R, Taka H, Takamori K, Ogawa H, Yamakura F: Detection of 6-nitrotryptophan in proteins by Western blot analysis and its application for peroxynitrite-treated PC12 cells. Nitric Oxide. 2007 Feb;16(1):18-28. Epub 2006 May 4. [16765071 ]
Liu L, Li Y, Zhu Y, Du G, Chen J: Redistribution of carbon flux in Torulopsis glabrata by altering vitamin and calcium level. Metab Eng. 2007 Jan;9(1):21-9. Epub 2006 Aug 12. [17008113 ]

Target Details

5. Pyruvate kinase PKLR

General Function:: Pyruvate kinase activity
Specific Function:: Plays a key role in glycolysis.
Gene Name:: PKLR
Uniprot ID:: P30613
Molecular Weight:: 61829.575 Da

References

Percy MJ, van Wijk R, Haggan S, Savage GA, Boyd K, Dempsey S, Hamilton J, Kettle P, Kyle A, Shepherd CW, van Solinge WW, Lappin TR, McMullin MF: Pyruvate kinase deficient hemolytic anemia in the Northern Irish population. Blood Cells Mol Dis. 2007 Sep-Oct;39(2):189-94. Epub 2007 Jun 15. [17574881 ]
Meza NW, Quintana-Bustamante O, Puyet A, Rio P, Navarro S, Diez A, Bueren JA, Bautista JM, Segovia JC: In vitro and in vivo expression of human erythrocyte pyruvate kinase in erythroid cells: a gene therapy approach. Hum Gene Ther. 2007 Jun;18(6):502-14. [17547515 ]
Rajaseger G, Lim CL, Lee KW, Arjunan P, Jia L, Moochhala S: Profiling of hepatocellular proteins by 1D PAGE-MALDI/MS/MS in a rat heat stress model. Front Biosci. 2006 Sep 1;11:2924-8. [16720364 ]
Xu J, Christian B, Jump DB: Regulation of rat hepatic L-pyruvate kinase promoter composition and activity by glucose, n-3 polyunsaturated fatty acids, and peroxisome proliferator-activated receptor-alpha agonist. J Biol Chem. 2006 Jul 7;281(27):18351-62. Epub 2006 Apr 27. [16644726 ]
Suzuki T, Kawamoto M, Murai A, Muramatsu T: Identification of the regulatory region of the L-type pyruvate kinase gene in mouse liver by hydrodynamics-based gene transfection. J Nutr. 2006 Jan;136(1):16-20. [16365052 ]

Target Details

6. Pyruvate kinase PKM

General Function:: Pyruvate kinase activity
Specific Function:: Glycolytic enzyme that catalyzes the transfer of a phosphoryl group from phosphoenolpyruvate (PEP) to ADP, generating ATP. Stimulates POU5F1-mediated transcriptional activation. Plays a general role in caspase independent cell death of tumor cells. The ratio betwween the highly active tetrameric form and nearly inactive dimeric form determines whether glucose carbons are channeled to biosynthetic processes or used for glycolytic ATP production. The transition between the 2 forms contributes to the control of glycolysis and is important for tumor cell proliferation and survival.
Gene Name:: PKM
Uniprot ID:: P14618
Molecular Weight:: 57936.38 Da

References

Li Y, Chang Y, Zhang L, Feng Q, Liu Z, Zhang Y, Zuo J, Meng Y, Fang F: High glucose upregulates pantothenate kinase 4 (PanK4) and thus affects M2-type pyruvate kinase (Pkm2). Mol Cell Biochem. 2005 Sep;277(1-2):117-25. [16132722 ]
Stetak A, Veress R, Ovadi J, Csermely P, Keri G, Ullrich A: Nuclear translocation of the tumor marker pyruvate kinase M2 induces programmed cell death. Cancer Res. 2007 Feb 15;67(4):1602-8. [17308100 ]
Vlaeminck-Guillem V, Safi R, Guillem P, Leteurtre E, Duterque-Coquillaud M, Laudet V: Thyroid hormone receptor expression in the obligatory paedomorphic salamander Necturus maculosus. Int J Dev Biol. 2006;50(6):553-60. [16741870 ]
Weinberger R, Appel B, Stein A, Metz Y, Neheman A, Barak M: The pyruvate kinase isoenzyme M2 (Tu M2-PK) as a tumour marker for renal cell carcinoma. Eur J Cancer Care (Engl). 2007 Jul;16(4):333-7. [17587357 ]
Staib P, Hoffmann M, Schinkothe T: Plasma levels of tumor M2-pyruvate kinase should not be used as a tumor marker for hematological malignancies and solid tumors. Clin Chem Lab Med. 2006;44(1):28-31. [16375581 ]

Target Details

7. 4-aminobutyrate aminotransferase, mitochondrial

General Function:: Succinate-semialdehyde dehydrogenase binding
Specific Function:: Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:: ABAT
Uniprot ID:: P80404
Molecular Weight:: 56438.405 Da

References

Andersen G, Andersen B, Dobritzsch D, Schnackerz KD, Piskur J: A gene duplication led to specialized gamma-aminobutyrate and beta-alanine aminotransferase in yeast. FEBS J. 2007 Apr;274(7):1804-17. Epub 2007 Mar 12. [17355287 ]
Schmidt C, Hofmann U, Kohlmuller D, Murdter T, Zanger UM, Schwab M, Hoffmann GF: Comprehensive analysis of pyrimidine metabolism in 450 children with unspecific neurological symptoms using high-pressure liquid chromatography-electrospray ionization tandem mass spectrometry. J Inherit Metab Dis. 2005;28(6):1109-22. [16435204 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]

Target Details

8. Alanine--glyoxylate aminotransferase 2, mitochondrial

General Function:: Pyridoxal phosphate binding
Specific Function:: Can metabolize asymmetric dimethylarginine (ADMA) via transamination to alpha-keto-delta-(NN-dimethylguanidino) valeric acid (DMGV). ADMA is a potent inhibitor of nitric-oxide (NO) synthase, and this activity provides mechanism through which the kidney regulates blood pressure.
Gene Name:: AGXT2
Uniprot ID:: Q9BYV1
Molecular Weight:: 57155.905 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
Tamaki N, Fujimoto S, Mizota C, Kaneko M, Kikugawa M: Inhibitory effect of 6-azauracil on beta-alanine metabolism in rat. J Nutr Sci Vitaminol (Tokyo). 1989 Oct;35(5):451-61. [2632679 ]

Target Details

9. Alpha-ketoglutarate-dependent dioxygenase FTO

General Function:: Oxidative rna demethylase activity
Specific Function:: Dioxygenase that repairs alkylated DNA and RNA by oxidative demethylation. Has highest activity towards single-stranded RNA containing 3-methyluracil, followed by single-stranded DNA containing 3-methylthymine. Has low demethylase activity towards single-stranded DNA containing 1-methyladenine or 3-methylcytosine (PubMed:18775698, PubMed:20376003). Specifically demethylates N(6)-methyladenosine (m6A) RNA, the most prevalent internal modification of messenger RNA (mRNA) in higher eukaryotes (PubMed:22002720, PubMed:26458103). Has no activity towards 1-methylguanine. Has no detectable activity towards double-stranded DNA. Requires molecular oxygen, alpha-ketoglutarate and iron. Contributes to the regulation of the global metabolic rate, energy expenditure and energy homeostasis. Contributes to the regulation of body size and body fat accumulation (PubMed:18775698, PubMed:20376003).
Gene Name:: FTO
Uniprot ID:: Q9C0B1
Molecular Weight:: 58281.53 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
IC50	>1000 uM	Not Available	BindingDB 19473

References

Aik W, Demetriades M, Hamdan MK, Bagg EA, Yeoh KK, Lejeune C, Zhang Z, McDonough MA, Schofield CJ: Structural basis for inhibition of the fat mass and obesity associated protein (FTO). J Med Chem. 2013 May 9;56(9):3680-8. doi: 10.1021/jm400193d. Epub 2013 Apr 23. [23547775 ]

Target Details

10. Monocarboxylate transporter 3

General Function:: Symporter activity
Specific Function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate (By similarity).
Gene Name:: SLC16A8
Uniprot ID:: O95907
Molecular Weight:: 52318.215 Da

References

Jansen S, Esmaeilpour T, Pantaleon M, Kaye PL: Glucose affects monocarboxylate cotransporter (MCT) 1 expression during mouse preimplantation development. Reproduction. 2006 Mar;131(3):469-79. [16514190 ]

Target Details

11. Monocarboxylate transporter 4

General Function:: Symporter activity
Specific Function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate (By similarity).
Gene Name:: SLC16A3
Uniprot ID:: O15427
Molecular Weight:: 49468.9 Da

References

Shimada A, Nakagawa Y, Morishige H, Yamamoto A, Fujita T: Functional characteristics of H+ -dependent nicotinate transport in primary cultures of astrocytes from rat cerebral cortex. Neurosci Lett. 2006 Jan 16;392(3):207-12. Epub 2005 Oct 5. [16213084 ]

Target Details

12. Monocarboxylate transporter 6

General Function:: Symporter activity
Specific Function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate (By similarity).
Gene Name:: SLC16A5
Uniprot ID:: O15375
Molecular Weight:: 54993.04 Da

References

Bonen A, Heynen M, Hatta H: Distribution of monocarboxylate transporters MCT1-MCT8 in rat tissues and human skeletal muscle. Appl Physiol Nutr Metab. 2006 Feb;31(1):31-9. [16604139 ]

Target Details

13. Monocarboxylate transporter 7

General Function:: Symporter activity
Specific Function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate (By similarity).
Gene Name:: SLC16A6
Uniprot ID:: O15403
Molecular Weight:: 57392.83 Da

References

Bonen A, Heynen M, Hatta H: Distribution of monocarboxylate transporters MCT1-MCT8 in rat tissues and human skeletal muscle. Appl Physiol Nutr Metab. 2006 Feb;31(1):31-9. [16604139 ]

Target Details

14. Monocarboxylate transporter 8

General Function:: Transporter activity
Specific Function:: Very active and specific thyroid hormone transporter. Stimulates cellular uptake of thyroxine (T4), triiodothyronine (T3), reverse triiodothyronine (rT3) and diidothyronine. Does not transport Leu, Phe, Trp or Tyr.
Gene Name:: SLC16A2
Uniprot ID:: P36021
Molecular Weight:: 59510.86 Da

References

Bonen A, Heynen M, Hatta H: Distribution of monocarboxylate transporters MCT1-MCT8 in rat tissues and human skeletal muscle. Appl Physiol Nutr Metab. 2006 Feb;31(1):31-9. [16604139 ]

Target Details

15. Pyruvate dehydrogenase E1 component subunit beta, mitochondrial

General Function:: Pyruvate dehydrogenase activity
Specific Function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHB
Uniprot ID:: P11177
Molecular Weight:: 39233.1 Da

References

Kumar V, Rangaraj N, Shivaji S: Activity of pyruvate dehydrogenase A (PDHA) in hamster spermatozoa correlates positively with hyperactivation and is associated with sperm capacitation. Biol Reprod. 2006 Nov;75(5):767-77. Epub 2006 Jul 19. [16855207 ]

Target Details

16. Solute carrier organic anion transporter family member 2A1

General Function:: Sodium-independent organic anion transmembrane transporter activity
Specific Function:: May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, as well as PGE1, PGE2 and PGF2A.
Gene Name:: SLCO2A1
Uniprot ID:: Q92959
Molecular Weight:: 70043.33 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	26 uM	Not Available	BindingDB 19473

References

Chan BS, Endo S, Kanai N, Schuster VL: Identification of lactate as a driving force for prostanoid transport by prostaglandin transporter PGT. Am J Physiol Renal Physiol. 2002 Jun;282(6):F1097-102. [11997326 ]

Pyruvic acid (T3D4325)

Structure for T3D4325: Pyruvic acid

Targets

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Binding/Activity Constants

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