PYRUVIC ACID
Relevant Data
Food Additives Approved by WHO:
Flavouring Substances Approved by European Union:
General Information
| Mainterm | PYRUVIC ACID |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 127-17-3 |
| Regnum |
172.515 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 1060 |
| IUPAC Name | 2-oxopropanoic acid |
| InChI | InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) |
| InChI Key | LCTONWCANYUPML-UHFFFAOYSA-N |
| Canonical SMILES | CC(=O)C(=O)O |
| Molecular Formula | C3H4O3 |
| Wikipedia | pyruvic acid |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 88.062 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 84.0 |
| CACTVS Substructure Key Fingerprint | A A A D c Y B A M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A C A S A g A A C C A A A A g A I A I C Q C A I A A A A A A A A A A A F A A A A A A A A A A A A A Q A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 54.4 |
| Monoisotopic Mass | 88.016 |
| Exact Mass | 88.016 |
| XLogP3 | None |
| XLogP3-AA | -0.3 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 6 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9401 |
| Human Intestinal Absorption | HIA+ | 0.9753 |
| Caco-2 Permeability | Caco2- | 0.6934 |
| P-glycoprotein Substrate | Non-substrate | 0.8153 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9498 |
| Non-inhibitor | 0.9514 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9490 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8783 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7951 |
| CYP450 2D6 Substrate | Non-substrate | 0.9402 |
| CYP450 3A4 Substrate | Non-substrate | 0.7806 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9800 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9608 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9697 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9834 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9882 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9932 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9883 |
| Non-inhibitor | 0.9801 | |
| AMES Toxicity | Non AMES toxic | 0.8578 |
| Carcinogens | Carcinogens | 0.5171 |
| Fish Toxicity | Low FHMT | 0.6827 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9718 |
| Honey Bee Toxicity | High HBT | 0.7062 |
| Biodegradation | Ready biodegradable | 0.9262 |
| Acute Oral Toxicity | III | 0.7364 |
| Carcinogenicity (Three-class) | Non-required | 0.7607 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.4055 | LogS |
| Caco-2 Permeability | 0.5437 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7859 | LD50, mol/kg |
| Fish Toxicity | 2.9093 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.9576 | pIGC50, ug/L |
From admetSAR
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 | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Keto acids and derivatives |
| Subclass | Alpha-keto acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Alpha-keto acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| 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 |
| Description | This compound 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. |
From ClassyFire
Targets
- 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
- 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 ]
- 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
- Pierre K, Pellerin L: Monocarboxylate transporters in the central nervous system: distribution, regulation and function. J Neurochem. 2005 Jul;94(1):1-14. [15953344 ]
- 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
- 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 ]
- 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
- 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 ]
- 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
- 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 ]
- 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
- 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 ]
- 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
- 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 ]
- 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
- 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 ]
- 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
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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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
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 ]
From T3DB