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5269:
5002:
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5307:
5188:
2027:
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5127:
5120:
36:
334:
222:
2053:. All metabolic pathways that are interlinked with the TCA cycle, including the metabolism of carbohydrates, amino acids, fatty acids, cholesterol, and heme, rely on the temporary formation of succinate. The intermediate is made available for biosynthetic processes through multiple pathways, including the reductive branch of the TCA cycle or the glyoxylate cycle, which are able to drive net production of succinate. In rodents, mitochondrial concentrations are approximately ~0.5 mM while plasma concentration are only 2–20 μM.
45:
2231:
27:
5317:
4930:
2097:
5240:
4992:
695:
1233:(BDO) can be synthesized using succinic acid as a precursor. The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. Succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications.
5279:
2717:
machinery or induce oxidative damage to proteins, membranes, organelles etc. In animal models, pharmacological inhibition of ischemic succinate accumulation ameliorated ischemia-reperfusion injury. As of 2016 the inhibition of succinate-mediated ROS production was under investigation as a therapeutic
2244:
Extracellular succinate can act as a signaling molecule with hormone-like functions in stimulating a variety of cells such as those in the blood, adipose tissues, immune tissues, liver, heart, retina and kidney. Extracellular succinate works by binding to and thereby activating the GPR91 (also termed
3079:
Chouchani, ET; Pell, VR; Gaude, E; Aksentijević, D; Sundier, SY; Robb, EL; Logan, A; Nadtochiy, SM; Ord, EN; Smith, AC; Eyassu, F; Shirley, R; Hu, CH; Dare, AJ; James, AM; Rogatti, S; Hartley, RC; Eaton, S; Costa, AS; Brookes, PS; Davidson, SM; Duchen, MR; Saeb-Parsy, K; Shattock, MJ; Robinson, AJ;
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or energetic misbalance are all linked to an alteration of flux through the TCA cycle and succinate accumulation. Upon exiting the mitochondria, succinate serves as a signal of metabolic state, communicating to neighboring cells how metabolically active the originating cell population is. As such,
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5031:
4957:
2234:
Amino acid sequence of GPR91 (also termed SUCNR1). Succinate binds to GPR91, a 7-transmembrane G-protein coupled receptor, located on a variety of cell types. Red amino acids represent those involved in binding succinate. All other amino acids are colored according to their chemical properties
2201:
and the blood stream where it is recognized by target receptors. In general, leakage from the mitochondria requires succinate overproduction or underconsumption and occurs due to reduced, reverse or completely absent activity of SDH or alternative changes in metabolic state. Mutations in SDH,
2529:
then generates a ferryl intermediate coordinated to succinate, which serves to oxidize the bound primary substrate. Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. Thus, via enzymatic inhibition, increased
2574:
pathway. Since PHDs have an absolute requirement for molecular oxygen, this process is suppressed in hypoxia allowing HIF1α to escape destruction. High concentrations of succinate will mimic the hypoxia state by suppressing PHDs, therefore stabilizing HIF1α and inducing the transcription of
2030:
Biological roles of succinate. Inside the mitochondria, succinate serves as an intermediate in multiple metabolic pathways and contributes to the generation of ROS. Outside the mitochondria, succinate functions as both an intracellular and extracellular signaling molecule. OOA=oxaloacetate;
5069:
5157:
2525:. First, 2-oxoglutarate coordinates with an Fe(II) ion bound to a conserved 2-histidinyl–1-aspartyl/glutamyl triad of residues present in the enzymatic center. Subsequently, the primary substrate enters the binding pocket and lastly dioxygen binds to the enzyme-substrate complex.
1978:, which converts two two-carbon acetyl units into the four-carbon succinate. The glyoxylate cycle is utilized by many bacteria, plants and fungi and allows these organisms to subsist on acetate or acetyl CoA yielding compounds. The pathway avoids the
2692:. Additionally, succinate-promoted activation of HIF-1α generates a pseudo-hypoxic state that can promote tumorneogensis by transcriptional activation of genes involved in proliferation, metabolism and angiogenesis. The other two oncometabolites,
1949:. This pathway is exploited in metabolic engineering to net generate succinate for human use. Additionally, succinic acid produced during the fermentation of sugar provides a combination of saltiness, bitterness and acidity to fermented alcohols.
3573:
2010:
into succinate, bypassing the TCA cycle intermediate succinyl-CoA and instead producing the intermediate GABA. Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to the formation of GABA. GABA is then metabolized by
2031:
a-KG=alpha ketoglutarate; GLUT= Glutamate; GABA = gamma-aminobutyric acid; SSA=Succinic semialdehyde; PHD= prolyl hydroxylase; HIF-1a=hypoxia inducible factor 1a; TET= Ten-eleven
Translocation Enzymes; JMJD3= Histone demethylase Jumonji D3
1797:
1401:
5355:
2827:
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Accumulated succinate inhibits dioxygenases, such as histone and DNA demethylases or prolyl hydroxylases, by competitive inhibition. Thus, succinate modifies the epigenic landscape and regulates gene expression.
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5040:
4966:
2570:. In humans, three HIF prolyl 4-hydroxylases regulate the stability of HIFs. Hydroxylation of two prolyl residues in HIF1α facilitates ubiquitin ligation, thus marking it for proteolytic destruction by the
2712:
through increased ROS production. During ischemia, succinate accumulates. Upon reperfusion, succinate is rapidly oxidized leading to abrupt and extensive production of ROS. ROS then trigger the cellular
5268:
2193:
In addition to its metabolic roles, succinate serves as an intracellular and extracellular signaling molecule. Extra-mitochondrial succinate alters the epigenetic landscape by inhibiting the family of
2215:
Succinate requires specific transporters to move through both the mitochondrial and plasma membrane. Succinate exits the mitochondrial matrix and passes through the inner mitochondrial membrane via
3577:
4418:
Hewitson, K. S.; Granatino, N.; Welford, R. W. D.; McDonough, M. A.; Schofield, C. J. (2005-04-15). "Oxidation by 2-oxoglutarate oxygenases: non-haem iron systems in catalysis and signalling".
2850:
2304:(i.e., concentration that induces a half maximal response) for stimulating GPR91 in the 20–50 μM range. Succinate's activation of the GPR91 receptor simulates a wide range of cell types and
2223:, nonspecific protein channels that facilitate the diffusion of molecules less than 1.5 kDa. Transport across the plasma membrane is likely tissue specific. A key candidate transporter is
5362:
2023:(SSADH) to form succinate, re-entering the TCA cycle and closing the loop. Enzymes required for the GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells.
2550:(KDM). Pathologically elevated levels of succinate lead to hypermethylation, epigenetic silencing and changes in neuroendocrine differentiation, potentially driving cancer formation.
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are not directly affected by succinate and HIF1. The mechanism by which succinate accumulates in immune cells is not fully understood. Activation of inflammatory macrophages through
1850:
1847:
1835:
1815:
1811:
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1439:
1419:
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2513:. 2-oxoglutarate-dependent dioxygenases require an iron cofactor to catalyze hydroxylations, desaturations and ring closures. Simultaneous to substrate oxidation, they convert
2219:, primarily SLC25A10, a succinate-fumarate/malate transporter. In the second step of mitochondrial export, succinate readily crosses the outer mitochondrial membrane through
2612:. For dendritic cells, succinate functions as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production. In inflammatory
3423:"1,4-Butanediol (BDO) Market Analysis By Application (Tetrahydrofuran, Polybutylene Teraphthalate, Gamma-Butyrolactone & Polyurethanes), And Segment Forecasts To 2020"
2632:
induces a metabolic shift towards glycolysis. In spite of a general downregulation of the TCA cycle under these conditions, succinate concentration is increased. However,
5001:
5229:
4256:
Krzak G, Willis CM, Smith JA, Pluchino S, Peruzzotti-Jametti L (January 2021). "Succinate
Receptor 1: An Emerging Regulator of Myeloid Cell Function in Inflammation".
2071:(ROS) production by directing electron flow in the electron transport chain. Under conditions of succinate accumulation, rapid oxidation of succinate by SDH can drive
5306:
5187:
3498:
3626:
Dröse, Stefan (2013-05-01). "Differential effects of complex II on mitochondrial ROS production and their relation to cardioprotective pre- and postconditioning".
3199:
4586:"Inhibition of hypoxia-inducible factor (HIF) hydroxylases by citric acid cycle intermediates: possible links between cell metabolism and stabilization of HIF"
2882:
Chikhalia, V.; Forbes, R.T.; Storey, R.A.; Ticehurst, M. (January 2006). "The effect of crystal morphology and mill type on milling induced crystal disorder".
2261:
gene. Arg, His, Arg, and Arg near the center of the GPR91 protein generate a positively charged binding site for succinate. GPR91 resides on its target cells'
831:. Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating
4213:
Fernández-Veledo S, Ceperuelo-Mallafré V, Vendrell J (September 2021). "Rethinking succinate: an unexpected hormone-like metabolite in energy homeostasis".
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is unable to accommodate excess electrons supplied by succinate oxidation, it forces electrons to flow backwards along the electron transport chain. RET at
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1839:
1809:
1808:
1804:
1452:
1443:
1413:
1412:
1408:
3524:
2235:(grey=nonpolar, cyan=negative charge, dark blue = positive charge, green=aromatic, dark purple=polar and noncharged, orange/light purple = special cases).
1952:
Accumulation of fumarate can drive the reverse activity of SDH, thus enhancing succinate generation. Under pathological and physiological conditions, the
1275:
in the food and beverage industry. It is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste. As an
5348:
4358:"Inhibition of α-KG-dependent histone and DNA demethylases by fumarate and succinate that are accumulated in mutations of FH and SDH tumor suppressors"
2118:
2111:
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2652:
Succinate is one of three oncometabolites, metabolic intermediates whose accumulation causes metabolic and non-metabolic dysregulation implicated in
1812:
1416:
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1381:
and three 2Fe-2S clusters. Succinate thus serves as a direct electron donor to the electron transport chain, and itself is converted into fumarate.
4799:
King, A.; Selak, M. A.; Gottlieb, E. (2006-01-01). "Succinate dehydrogenase and fumarate hydratase: linking mitochondrial dysfunction and cancer".
2575:
HIF1-dependent genes even under normal oxygen conditions. HIF1 is known to induce transcription of more than 60 genes, including genes involved in
2608:
or GPR91 signaling in innate immune cells. Through these mechanisms, succinate accumulation has been shown to regulate production of inflammatory
1827:
1431:
2006:(GABA) shunt into the TCA cycle, a closed cycle which synthesizes and recycles GABA. The GABA shunt serves as an alternate route to convert
3538:
Zeikus, J. G.; Jain, M. K.; Elankovan, P. (1999). "Biotechnology of succinic acid production and markets for derived industrial products".
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1830:
1816:
1447:
1434:
1420:
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2616:, succinate-induced stability of HIF1 results in increased transcription of HIF1-dependent genes, including the pro-inflammatory cytokine
2083:, the complex normally preceding SDH in the electron transport chain, leads to ROS production and creates a pro-oxidant microenvironment.
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2685:
2498:
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1450:
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Tannahill, GM; Curtis, AM; Adamik, J; Palsson-McDermott, EM; McGettrick, AF; Goel, G; Frezza, C; Bernard, NJ; Kelly, B (2013-04-11).
2459:
is debated. Multiple studies have demonstrated succinate-induced aggregation, but the effect has high inter-individual variability.
3374:
2207:
succinate links TCA cycle dysfunction or metabolic changes to cell-cell communication and to oxidative stress-related responses.
2076:
1832:
1436:
4356:
Xiao, Mengtao; Yang, Hui; Xu, Wei; Ma, Shenghong; Lin, Huaipeng; Zhu, Honguang; Liu, Lixia; Liu, Ying; Yang, Chen (2012-06-15).
3941:
de Castro
Fonseca, Matheus; Aguiar, Carla J.; da Rocha Franco, Joao Antônio; Gingold, Rafael N.; Leite, M. Fatima (2016-01-01).
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succinate load can lead to changes in transcription factor activity and genome-wide alterations in histone and DNA methylation.
1853:
1825:
1800:
1457:
1429:
1404:
4852:
3368:"Top Value Added Chemicals from Biomass, Volume 1: Results of Screening for Potential Candidates from Sugars and Synthesis Gas"
2688:. Inhibition of KDMs and TET hydroxylases results in epigenetic dysregulation and hypermethylation affecting genes involved in
1838:
1801:
1442:
1405:
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2795:
1373:. This enzyme complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of
255:
3449:"Design and Applications of Biodegradable Polyester Tissue Scaffolds Based on Endogenous Monomers Found in Human Metabolism"
2161:
5632:
2475:
via GPR91. Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.
2227:(I'm not dead yet), a sodium-independent anion exchanger, which moves both dicarboxylate and citrate into the bloodstream.
846:
Dysregulation of succinate synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as
2133:
1840:
1805:
1444:
1409:
1017:
of these processes are 4.3 and 5.6, respectively. Both anions are colorless and can be isolated as the salts, e.g., Na(CH
5371:
2067:
The activity of succinate dehydrogenase (SDH), which interconverts succinate into fumarate participates in mitochondrial
2020:
703:
3273:
Otero, José Manuel; Cimini, Donatella; Patil, Kiran R.; Poulsen, Simon G.; Olsson, Lisbeth; Nielsen, Jens (2013-01-21).
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via GPR91. This leads to stellate cell activation and fibrogenesis. Thus, succinate is thought to play a role in liver
1824:
1428:
1925:
Succinate can alternatively be formed by reverse activity of SDH. Under anaerobic conditions certain bacteria such as
1854:
1807:
1458:
1411:
1279:
in pharmaceutical products, it is also used to control acidity or as a counter ion. Drugs involving succinate include
3751:
Haas, Robert; Cucchi, Danilo; Smith, Joanne; Pucino, Valentina; Macdougall, Claire
Elizabeth; Mauro, Claudio (2016).
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SUCNR1 is one of the highest expressed G protein-coupled receptors on human platelets, present at levels similar to
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2644:. Succinate may thus be produced from enhanced glutamine metabolism via alpha-ketoglutarate or the GABA shunt.
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In 2004, succinate was placed on the US Department of Energy's list of top 12 platform chemicals from biomass.
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Philosophical
Transactions of the Royal Society of London A: Mathematical, Physical and Engineering Sciences
3879:
Pell, Victoria R.; Chouchani, Edward T.; Frezza, Christian; Murphy, Michael P.; Krieg, Thomas (2016-07-15).
3821:"The succinate receptor as a novel therapeutic target for oxidative and metabolic stress-related conditions"
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on the cells that express this receptor. Most studies have reported that the GPR91 protein consists of 330
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217:
2129:
1098:
Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes.
5652:
5637:
5613:
2425:
1378:
312:
2566:. PHDs hydroxylate proline in parallel to oxidatively decarboxylating 2-oxyglutarate to succinate and CO
2336:
Succinate signaling often occurs in response to hypoxic conditions. In the liver, succinate serves as a
4880:
4857:
2779:
2697:
2684:. The oncogenic mechanism caused by mutated SHD is thought to relate to succinate's ability to inhibit
2266:
2072:
1920:
1011:
559:
2700:
have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms.
159:
2823:
2526:
2380:
viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte
1197:. Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and
1138:. Global production is estimated at 16,000 to 30,000 tons a year, with an annual growth rate of 10%.
5340:
2026:
4584:
Koivunen, P; Hirsilä, M; Remes, AM; Hassinen, IE; Kivirikko, KI; Myllyharju, J (16 February 2007).
2776:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
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3275:"Industrial Systems Biology of Saccharomyces cerevisiae Enables Novel Succinic Acid Cell Factory"
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2003:
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2977:"Succinate, an intermediate in metabolism, signal transduction, ROS, hypoxia, and tumorigenesis"
5126:
5119:
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Mills, Evanna; O'Neill, Luke A.J. (May 2014). "Succinate: a metabolic signal in inflammation".
2510:
2433:
1881:
1370:
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817:
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2309:
2016:
1937:, run the TCA cycle in reverse and convert glucose to succinate through the intermediates of
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by distillation and has thus been known as spirit of amber. Common industrial routes include
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3286:
3093:
3082:"Ischaemic accumulation of succinate controls reperfusion injury through mitochondrial ROS"
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sub-type of receptor that, depending on the cell type bearing it, interacts with multiple
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Peti-Peterdi, János; Gevorgyan, Haykanush; Lam, Lisa; Riquier-Brison, Anne (2012-06-23).
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2668:, cause pathological increase in succinate. SDH mutations have also been identified in
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1994:. Generated succinate is then available for either energy production or biosynthesis.
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Thakker, Chandresh; Martínez, Irene; San, Ka-Yiu; Bennett, George N. (2017-03-07).
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can increase mitochondrial fumarate, which is then readily converted to succinate.
1938:
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773:
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634:
478:
406:
4156:
Gilissen, Julie; Jouret, François; Pirotte, Bernard; Hanson, Julien (2016-03-01).
3881:"Succinate metabolism: a new therapeutic target for myocardial reperfusion injury"
2467:
Succinate serves as a modulator of blood pressure by stimulating renin release in
1322:, a primary metabolic pathway used to produce chemical energy in the presence of O
4867:
4013:
3996:
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2384:. Stimulation of GPR91 triggers at least two signaling pathways in the heart: a
5555:
5285:
4684:"Metabolic reprogramming in macrophages and dendritic cells in innate immunity"
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by triggering the activity of antigen-presenting cells that, in turn, activate
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1987:
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Click on genes, proteins and metabolites below to link to respective articles.
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Ariza, Ana
Carolina; Deen, Peter M. T.; Robben, Joris Hubertus (2012-01-01).
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pathway which changes the pattern of Ca uptake and distribution and triggers
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4744:"Oncometabolites: Unconventional triggers of oncogenic signalling cascades"
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Succinate accumulation under hypoxic conditions has been implicated in the
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Succinic acid is a white, odorless solid with a highly acidic taste. In an
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1053:. In living organisms, primarily succinate, not succinic acid, is found.
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2620:. Other inflammatory cytokines produced by activated macrophages such as
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820:, and as a signaling molecule reflecting the cellular metabolic state.
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4624:
4298:
3753:"Intermediates of Metabolism: From Bystanders to Signalling Molecules"
3051:
5370:
5197:
5061:
4539:
3666:
Cheng, Ke-Ke; Wang, Gen-Yu; Zeng, Jing; Zhang, Jian-An (2013-04-18).
2975:
Tretter, Laszlo; Patocs, Attila; Chinopoulos, Christos (2016-08-01).
2714:
2637:
2497:
Accumulation of either fumarate or succinate reduces the activity of
2325:
2321:
1276:
1236:
1222:
866:
5107:
5030:
4956:
3995:
Bardella, Chiara; Pollard, Patrick J.; Tomlinson, Ian (2011-11-01).
3574:"Overview of pharmaceutical excipients used in tablets and capsules"
2294:. This enables GPR91 to regulate a multitude of signaling outcomes.
2096:
843:, especially ATP formation, to the regulation of cellular function.
685:
Except where otherwise noted, data are given for materials in their
5023:
4929:
3630:. Respiratory complex II: Role in cellular physiology and disease.
2609:
2456:
2216:
535:
493:
229:
190:
935:, succinic acid undergoes two successive deprotonation reactions:
118:
5239:
5163:
5068:
4417:
4038:"Succinate as a New Actor in Pluripotency and Early Development?"
2257:
although a few studies have detected a 334 amino acid product of
1154:
836:
521:
507:
447:
267:
4991:
4863:
Calculator: Water and solute activities in aqueous succinic acid
3505:. 31 October 2015. Archived from the original on 31 October 2017
5156:
4984:
4522:
Yang, Ming; Soga, Tomoyoshi; Pollard, Patrick J. (2013-09-03).
3799:. In Siegel, GJ; Agranoff, BW; Albers, RW; et al. (eds.).
2935:. Toxnet National Library of Medicine HSDB Database. 2005-01-31
2437:
2385:
2246:
1153:
are proposed for the commercial production via fermentation of
1131:
854:, and degradation can lead to pathological conditions, such as
150:
3340:
Fieser, Louis F.; Martin, E. L. (1932). "Succinic
Anhydride".
3080:
Work, LM; Frezza, C; Krieg, T; Murphy, MP (20 November 2014).
3078:
2881:
2774:"CHAPTER P-6. Applications to Specific Classes of Compounds".
2265:
with its binding site facing the extracellular space. It is a
1212:
1087:
3943:"GPR91: expanding the frontiers of Krebs cycle intermediates"
3801:
2605:
2563:
2521:. 2-oxoglutarate-dependent dioxygenases bind substrates in a
2449:
2389:
1107:
874:
793:
549:
130:
108:
4627:"Succinate is a danger signal that induces IL-1β via HIF-1α"
4583:
3790:
3788:
3786:
317:
4155:
4086:
3164:
Boy
Cornils; Peter Lappe. "Dicarboxylic Acids, Aliphatic".
2600:
Metabolic signaling involving succinate can be involved in
2324:, the succinate-activated GPR91 signaling cascade inhibits
2298:
2049:
and its primary biological function is that of a metabolic
1900:
The interactive pathway map can be edited at WikiPathways:
920:
792:. In living organisms, succinic acid takes the form of an
739:
3576:. Modern Medicine Network. 24 October 2008. Archived from
2517:, also known as alpha-ketoglutarate, into succinate and CO
2392:
pathway that activates hypertrophic gene expression and a
2364:, triggering the activation of angiogenic factors such as
4524:"Oncometabolites: linking altered metabolism with cancer"
3878:
3783:
3223:
3067:
1247:
occurs when more than one succinate adds to a substrate.
1169:
or be converted to diesters, such as diethylsuccinate (CH
1081:
1072:
914:
905:
890:
757:
751:
628:
4255:
4087:
Gilissen J, Jouret F, Pirotte B, Hanson J (March 2016).
3994:
3668:"Improved Succinate Production by Metabolic Engineering"
2974:
4902:
3272:
3074:
3072:
3070:
357:
InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
4737:
4735:
3750:
3447:
Barrett, Devin G.; Yousaf, Muhammad N. (2009-10-12).
2983:. EBEC 2016: 19th European Bioenergetics Conference.
1084:
1078:
1075:
1069:
917:
911:
908:
902:
760:
754:
748:
742:
736:
367:
InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
230:
4742:
Sciacovelli, Marco; Frezza, Christian (2017-03-06).
4158:"Insight into SUCNR1 (GPR91) structure and function"
4089:"Insight into SUCNR1 (GPR91) structure and function"
3200:"NNFCC Renewable Chemicals Factsheet: Succinic Acid"
1914:
923:
4001:
Biochimica et Biophysica Acta (BBA) - Bioenergetics
3628:
Biochimica et Biophysica Acta (BBA) - Bioenergetics
3537:
2981:
Biochimica et Biophysica Acta (BBA) - Bioenergetics
2656:. Loss-of-function mutations in the genes encoding
2636:involved in the activation of macrophages increase
1066:
899:
839:-like signaling. As such, succinate links cellular
745:
254:
4732:
4579:
4577:
4575:
4469:
4467:
4465:
4413:
4411:
4409:
4151:
4149:
4147:
4145:
4143:
4141:
3990:
3988:
3936:
3665:
3605:
3163:
2197:. Alternative, succinate can be released into the
462:184–190 °C (363–374 °F; 457–463 K)
4798:
4741:
3934:
3932:
3930:
3928:
3926:
3924:
3922:
3920:
3918:
3916:
3601:
3599:
3597:
3595:
3219:
3217:
3215:
3213:
2970:
2548:JmjC domain-containing histone lysine demethylase
2331:
2297:Succinate has a high affinity for GPR91, with an
1303:
5624:
4681:
4474:Yang, Ming; Pollard, Patrick J. (10 June 2013).
3523:: CS1 maint: bot: original URL status unknown (
3028:
2968:
2966:
2964:
2962:
2960:
2958:
2956:
2954:
2952:
2950:
2086:
2019:. Finally, succinic semialdehyde is oxidized by
1345:Succinyl-CoA + NDP + Pi → Succinate + CoA + NTP
279:
4572:
4521:
4462:
4406:
4305:Pflügers Archiv: European Journal of Physiology
4138:
3985:
3818:
3814:
3812:
3810:
3803:(6th ed.). Philadelphia: Lippincott-Raven.
3661:
3659:
3657:
3621:
3619:
3373:. U.S. Department of Energy. November 1, 2004.
1799:
1403:
94:
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4513:
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3746:
3744:
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3740:
3738:
3736:
3592:
3210:
3167:Ullmann's Encyclopedia of Industrial Chemistry
3024:
3022:
3020:
3018:
3016:
3014:
3012:
2703:
2045:Succinate is produced and concentrated in the
1250:
1106:Historically, succinic acid was obtained from
5356:
4888:
4035:
3795:Olsen, Richard W; DeLorey, Timothy M (1999).
3446:
2947:
1352:(SDH), succinate is subsequently oxidized to
4682:Kelly, Beth; O'Neill, Luke AJ (2015-07-01).
4355:
4249:
4206:
4080:
4029:
3807:
3794:
3654:
3616:
3400:Ashford's Dictionary of Industrial Chemicals
3339:
2828:Institute for Occupational Safety and Health
2509:and collagen prolyl-4-hydroxylases, through
2455:, though the role of succinate signaling in
1894:
4868:PubChem: Compound Summary for Succinic Acid
4508:
4473:
3863:
3733:
3009:
2884:European Journal of Pharmaceutical Sciences
2769:
2767:
2562:(PHDs) stabilizes the transcription factor
1365:SDH also participates in the mitochondrial
1213:Precursor to polymers, resins, and solvents
1189:. This diethyl ester is a substrate in the
865:Succinic acid is marketed as food additive
800:, which has multiple biological roles as a
5363:
5349:
4895:
4881:
3606:Berg, JM; Tymoczko, JL; Stryer, L (2002).
3402:(3rd ed.), Wavelength, p. 1517,
3226:"Succinate production in Escherichia coli"
3159:
3157:
2851:"Product Information Sheet: Succinic Acid"
2478:
2352:. In the retina, succinate accumulates in
2239:
332:
220:
178:
4775:
4715:
4658:
4601:
4555:
4491:
4389:
4332:
4181:
4063:
4053:
4012:
3968:
3958:
3896:
3846:
3836:
3701:
3683:
3499:"Succinic acid in the FDA SCOGS Database"
3474:
3464:
3316:
3298:
3249:
3113:
3050:
2992:
2845:
2843:
2841:
2839:
2837:
2835:
2403:
2400:-dependent hypertrophic gene activation.
2181:Learn how and when to remove this message
2040:
299:
2927:
2925:
2923:
2921:
2815:
2813:
2811:
2809:
2807:
2764:
2488:
2462:
2229:
2025:
2002:Succinate is the re-entry point for the
1271:. Succinic acid is used primarily as an
1101:
3724:
3397:
3154:
2590:
2408:SUCNR1 is highly expressed on immature
2315:
1377:via the intermediate electron carriers
1318:Succinate is a key intermediate in the
1165:Succinic acid can be dehydrogenated to
893:to form its conjugate base, succinate (
328:
198:
5625:
4301:"Metabolic control of renin secretion"
4215:Trends in Endocrinology and Metabolism
3612:(5th ed.). New York: W H Freeman.
3540:Applied Microbiology and Biotechnology
2832:
2443:
2416:. Furthermore, SUCNR1 synergizes with
2371:
2117:Please improve this article by adding
2035:
1982:steps of the TCA cycle via the enzyme
1193:. Dehydration of succinic acid gives
880:
616:206 °C (403 °F; 479 K)
472:235 °C (455 °F; 508 K)
211:
5344:
4876:
4528:The Journal of Clinical Investigation
3625:
2918:
2804:
2686:2-oxogluterate-dependent dioxygenases
2587:, cell survival, and tumor invasion.
2542:(ten-eleven translocation) family of
2533:
2499:2-oxoglutarate-dependent dioxygenases
2412:, where succinate binding stimulates
2360:succinate signaling promotes retinal
2195:2-oxogluterate-dependent dioxygenases
2077:mitochondrial respiratory complex III
1160:
360:Key: KDYFGRWQOYBRFD-UHFFFAOYSA-N
158:
138:
4476:"Succinate: A New Epigenetic Hacker"
3797:"GABA Synthesis, Uptake and Release"
2356:in response to ischemic conditions.
2090:
5372:Linear saturated dicarboxylic acids
4760:10.1016/j.freeradbiomed.2016.04.025
4748:Free Radical Biology & Medicine
4590:The Journal of Biological Chemistry
2739:, procured by heating succinic acid
2538:Succinate and fumarate inhibit the
2081:mitochondrial respiratory complex 1
2021:succinic semialdehyde dehydrogenase
1974:Succinate is also a product of the
1963:
370:Key: KDYFGRWQOYBRFD-UHFFFAOYAC
270:
13:
2553:
2376:Extracellular succinate regulates
1795:
1788:
1783:
1778:
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1758:
1753:
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1738:
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1523:
1518:
1513:
1508:
1503:
1498:
1493:
1488:
1483:
1478:
1473:
1399:
1130:. Succinate is also produced from
14:
5669:
4846:
4036:Detraux D, Renard P (July 2022).
3202:. 3 February 2010. Archived from
2660:, frequently found in hereditary
2056:
1915:Reductive branch of the TCA cycle
1359:Succinate + FAD → Fumarate + FADH
1269:U.S. Food and Drug Administration
5315:
5305:
5277:
5267:
5238:
5228:
5196:
5186:
5155:
5125:
5118:
5106:
5077:
5067:
5039:
5029:
5000:
4990:
4965:
4955:
4928:
4174:10.1016/j.pharmthera.2016.01.008
4108:10.1016/j.pharmthera.2016.01.008
3947:Cell Communication and Signaling
2647:
2564:hypoxia inducible factor (HIF)1α
2095:
1062:
895:
732:
693:
418:
43:
34:
25:
4792:
4675:
4618:
4349:
4292:
4162:Pharmacology & Therapeutics
4096:Pharmacology & Therapeutics
3718:
3566:
3531:
3491:
3440:
3415:
3391:
3380:from the original on 2013-10-21
3360:
3333:
3266:
3192:
2856:. Sigma Aldrich. Archived from
2670:gastrointestinal stromal tumors
2595:
2473:juxtaglomerular apparatus cells
2210:
1298:
1204:
1060:group it is called a succinyl (
689:(at 25 °C , 100 kPa).
3757:Trends in Biochemical Sciences
3130:
2875:
2780:The Royal Society of Chemistry
2546:DNA modifying enzymes and the
2420:to increase the production of
2332:Effect on the liver and retina
1326:. Succinate is generated from
1304:Tricarboxylic acid (TCA) cycle
869:. The name derives from Latin
829:tricarboxylic acid (TCA) cycle
424:
412:
1:
3672:BioMed Research International
2758:
2310:Functions regulated by SUCNR1
2119:secondary or tertiary sources
2087:Additional biologic functions
1997:
1239:with succinic acid is called
4014:10.1016/j.bbabio.2011.07.003
3640:10.1016/j.bbabio.2013.01.004
3300:10.1371/journal.pone.0054144
2994:10.1016/j.bbabio.2016.03.012
2501:, including histone and DNA
1265:generally recognized as safe
816:which is involved in making
484:58 g/L (20 °C) or 100 mg/mL
7:
5633:Citric acid cycle compounds
5614:Category:Dicarboxylic acids
3398:Ashford, Robert D. (2011),
2788:10.1039/9781849733069-00648
2725:
2704:Ischemia reperfusion injury
2680:, testicular seminomas and
2340:signal, released by anoxic
1251:Food and dietary supplement
835:landscape or demonstrating
10:
5674:
3825:Frontiers in Endocrinology
3769:10.1016/j.tibs.2016.02.003
2896:10.1016/j.ejps.2005.08.013
2523:sequential, ordered manner
2482:
2267:G protein-coupled receptor
2217:dicarboxylate transporters
2073:reverse electron transport
2060:
1967:
1921:Succinic acid fermentation
1918:
1307:
823:Succinate is generated in
5611:
5573:Hexadecanedioic acid
5387:
5151:
5124:
5117:
4944:
4918:
4913:
4493:10.1016/j.ccr.2013.05.015
4317:10.1007/s00424-012-1130-y
4227:10.1016/j.tem.2021.06.003
3997:"SDH mutations in cancer"
3960:10.1186/s12964-016-0126-1
3466:10.3390/molecules14104022
3043:10.1016/j.tcb.2013.11.008
2824:GESTIS Substance Database
2527:Oxidative decarboxylation
2422:proinflammatory cytokines
2366:endothelial growth factor
1958:purine nucleotide shuttle
683:
620:
605:
399:
379:
344:
78:
68:
56:
51:
42:
33:
24:
5592:(Phelogenic acid) C
5556:Tredecanedioic acid
4270:10.1016/j.it.2020.11.004
3838:10.3389/fendo.2012.00022
3354:10.15227/orgsyn.012.0066
3176:10.1002/14356007.a08_523
3138:"Definition of SUCCINYL"
2558:Succinate inhibition of
2432:. Succinate may enhance
1954:malate-aspartate shuttle
1367:electron transport chain
1348:Catalyzed by the enzyme
1320:tricarboxylic acid cycle
1310:Tricarboxylic acid cycle
1225:and a component of some
1150:Saccharomyces cerevisiae
889:, succinic acid readily
814:electron transport chain
5658:Metabolic intermediates
5539:Dodecanedioic acid
4362:Genes & Development
3885:Cardiovascular Research
3727:Knowing and Making Wine
3725:Peynaud, Emile (1984).
3170:. Weinheim: Wiley-VCH.
3142:www.merriam-webster.com
2658:succinate dehydrogenase
2479:Intracellular signaling
2240:Extracellular signaling
2069:reactive oxygen species
2063:Reactive Oxygen Species
2004:gamma-aminobutyric acid
1369:, where it is known as
1350:succinate dehydrogenase
1332:succinyl-CoA synthetase
1314:Succinate dehydrogenase
1141:Genetically engineered
810:succinate dehydrogenase
595:Magnetic susceptibility
5471:Heptanedioic acid
5437:(Glutaric acid) C
5435:Pentanedioic acid
5419:(Succinic acid) C
5405:(Malonic acid) CH
5403:Propanedioic acid
5395:(Oxalic acid) (CO
4813:10.1038/sj.onc.1209594
4603:10.1074/jbc.M610415200
4440:10.1098/rsta.2004.1540
4374:10.1101/gad.191056.112
4055:10.3390/metabo12070651
3242:10.1002/biot.201100061
3031:Trends in Cell Biology
2511:competitive inhibition
2494:
2404:Effect on immune cells
2354:retinal ganglion cells
2236:
2106:relies excessively on
2041:Metabolic intermediate
2032:
1865:
1469:
1371:respiratory complex II
802:metabolic intermediate
5575:(Thapsic acid) C
5524:(Sebacic acid) C
5522:Decanedioic acid
5507:(Azelaic acid) C
5505:Nonanedioic acid
5490:(Suberic acid) C
5488:Octanedioic acid
5473:(Pimelic acid) C
5453:Hexanedioic acid
5417:Butanedioic acid
5393:Ethanedioic acid
5086:CoA + ATP (GTP)
3552:10.1007/s002530051431
3230:Biotechnology Journal
2782:. 2014. p. 747.
2622:tumor necrosis factor
2604:via stabilization of
2492:
2463:Effect on the kidneys
2233:
2029:
2017:succinic semialdehyde
1935:M. succiniciproducens
1931:A. succiniciproducens
1864:
1468:
1293:solifenacin succinate
1285:sumatriptan succinate
1102:Commercial production
804:being converted into
5455:(Adipic acid) C
4258:Trends in Immunology
2690:cell differentiation
2591:Role in human health
2572:ubiquitin/proteasome
2457:platelet aggregation
2316:Effect on adipocytes
2199:extracellular milieu
1871:|alt=TCACycle_WP78
1289:doxylamine succinate
1281:metoprolol succinate
812:in complex 2 of the
73:1,4-Butanedioic acid
58:Preferred IUPAC name
4643:10.1038/nature11986
4432:2005RSPTA.363..807H
3685:10.1155/2013/538790
3580:on 19 February 2012
3427:Grand View Research
3291:2013PLoSO...854144O
3106:10.1038/nature13909
3098:2014Natur.515..431C
2634:lipopolysaccharides
2630:toll-like receptors
2560:prolyl hydroxylases
2507:prolyl hydroxylases
2444:Effect on platelets
2418:toll-like receptors
2372:Effect on the heart
2273:subtypes including
2036:Cellular metabolism
2008:alpha-ketoglutarate
1990:into succinate and
1263:, succinic acid is
1217:Succinic acid is a
1191:Stobbe condensation
881:Physical properties
862:and tissue injury.
479:Solubility in water
442: g·mol
238:(antioxidants, ...)
21:
5653:E-number additives
5638:Dicarboxylic acids
5590:Docosanedioic acid
5558:(Brassylic acid) C
4700:10.1038/cr.2015.68
3898:10.1093/cvr/cvw100
2863:on 7 November 2017
2710:reperfusion injury
2698:2-hydroxyglutarate
2534:Epigenetic effects
2495:
2362:neovascularization
2237:
2033:
1866:
1470:
1261:dietary supplement
1195:succinic anhydride
1161:Chemical reactions
716:Infobox references
621:Related compounds
19:
5620:
5619:
5338:
5337:
5333:
5332:
5093:+ ADP (GDP)
4907:metabolic pathway
4904:Citric acid cycle
4807:(34): 4675–4682.
4637:(7444): 238–242.
4426:(1829): 807–828.
4368:(12): 1326–1338.
4007:(11): 1432–1443.
3503:FDA GRAS Database
3459:(10): 4022–4050.
3409:978-0-9522674-3-0
3342:Organic Syntheses
2797:978-0-85404-182-4
2743:Citric acid cycle
2642:GABA transporters
2434:adaptive immunity
2430:interleukin-1beta
2263:surface membranes
2191:
2190:
2183:
2165:
2013:GABA transaminase
1342:-producing step:
1273:acidity regulator
770:dicarboxylic acid
724:Chemical compound
722:
721:
313:CompTox Dashboard
120:Interactive image
16:Dicarboxylic acid
5665:
5365:
5358:
5351:
5342:
5341:
5319:
5309:
5281:
5271:
5261:
5242:
5232:
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5200:
5190:
5181:
5159:
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5110:
5081:
5071:
5043:
5033:
5004:
4994:
4969:
4959:
4942:
4932:
4916:
4915:
4897:
4890:
4883:
4874:
4873:
4841:
4840:
4796:
4790:
4789:
4779:
4739:
4730:
4729:
4719:
4679:
4673:
4672:
4662:
4622:
4616:
4615:
4605:
4581:
4570:
4569:
4559:
4540:10.1172/JCI67228
4519:
4506:
4505:
4495:
4471:
4460:
4459:
4415:
4404:
4403:
4393:
4353:
4347:
4346:
4336:
4296:
4290:
4289:
4253:
4247:
4246:
4210:
4204:
4203:
4185:
4153:
4136:
4135:
4093:
4084:
4078:
4077:
4067:
4057:
4033:
4027:
4026:
4016:
3992:
3983:
3982:
3972:
3962:
3938:
3911:
3910:
3900:
3876:
3861:
3860:
3850:
3840:
3816:
3805:
3804:
3792:
3781:
3780:
3748:
3731:
3730:
3722:
3716:
3715:
3705:
3687:
3663:
3652:
3651:
3623:
3614:
3613:
3603:
3590:
3589:
3587:
3585:
3570:
3564:
3563:
3535:
3529:
3528:
3522:
3514:
3512:
3510:
3495:
3489:
3488:
3478:
3468:
3444:
3438:
3437:
3435:
3434:
3429:. September 2015
3419:
3413:
3412:
3395:
3389:
3388:
3386:
3385:
3379:
3372:
3364:
3358:
3357:
3337:
3331:
3330:
3320:
3302:
3270:
3264:
3263:
3253:
3221:
3208:
3207:
3206:on 20 July 2011.
3196:
3190:
3189:
3161:
3152:
3151:
3149:
3148:
3134:
3128:
3127:
3117:
3076:
3065:
3064:
3054:
3026:
3007:
3006:
2996:
2987:(8): 1086–1101.
2972:
2945:
2944:
2942:
2940:
2929:
2916:
2915:
2879:
2873:
2872:
2870:
2868:
2862:
2855:
2847:
2830:
2817:
2802:
2801:
2771:
2666:pheochromocytoma
2544:5-methylcytosine
2186:
2179:
2175:
2172:
2166:
2164:
2123:
2099:
2091:
1984:isocitrate lyase
1976:glyoxylate cycle
1970:Glyoxylate cycle
1964:Glyoxylate cycle
1907:
1906:
1898:
1791:
1786:
1781:
1776:
1771:
1766:
1761:
1756:
1751:
1746:
1741:
1736:
1731:
1726:
1721:
1716:
1711:
1706:
1701:
1696:
1691:
1686:
1681:
1676:
1671:
1666:
1661:
1656:
1651:
1646:
1641:
1636:
1631:
1626:
1621:
1616:
1611:
1606:
1601:
1596:
1591:
1586:
1581:
1576:
1571:
1566:
1561:
1556:
1551:
1546:
1541:
1536:
1531:
1526:
1521:
1516:
1511:
1506:
1501:
1496:
1491:
1486:
1481:
1476:
1144:Escherichia coli
1136:maleic anhydride
1094:
1093:
1090:
1089:
1086:
1083:
1080:
1077:
1074:
1071:
1068:
930:
929:
926:
925:
922:
919:
916:
913:
910:
907:
904:
901:
887:aqueous solution
858:transformation,
774:chemical formula
767:
766:
763:
762:
759:
756:
753:
750:
747:
744:
741:
738:
706:
700:
697:
696:
644:carboxylic acids
635:sodium succinate
601:-57.9·10 cm/mol
441:
426:
420:
414:
407:Chemical formula
391:C(CC(=O)O)C(=O)O
337:
336:
321:
319:
303:
283:
272:
258:
232:
224:
213:
202:
182:
162:
142:
122:
98:
62:Butanedioic acid
47:
38:
29:
22:
18:
5673:
5672:
5668:
5667:
5666:
5664:
5663:
5662:
5623:
5622:
5621:
5616:
5607:
5606:
5603:
5599:
5595:
5586:
5582:
5578:
5569:
5565:
5561:
5552:
5548:
5544:
5535:
5531:
5527:
5518:
5514:
5510:
5501:
5497:
5493:
5484:
5480:
5476:
5466:
5462:
5458:
5448:
5444:
5440:
5430:
5426:
5422:
5412:
5408:
5398:
5383:
5381:
5377:
5369:
5339:
5334:
5329:
5328:
5327:
5320:
5312:
5311:
5310:
5302:
5301:
5300:
5295:
5290:
5289:
5282:
5274:
5273:
5272:
5264:
5263:
5259:
5256:
5251:
5250:
5243:
5235:
5234:
5233:
5225:
5224:
5221:
5218:
5214:
5210:
5209:
5201:
5193:
5192:
5191:
5183:
5182:
5179:
5175:
5173:
5168:
5167:
5160:
5135:
5113:
5112:
5111:
5104:
5096:
5095:
5094:
5092:
5087:
5083:
5082:
5073:
5072:
5065:
5057:
5056:
5055:
5052:
5051:
5045:
5044:
5035:
5034:
5027:
5019:
5018:
5017:
5015:
5010:
5006:
5005:
4996:
4995:
4988:
4980:
4979:
4978:
4975:
4971:
4970:
4961:
4960:
4953:
4940:
4936:
4934:
4933:
4926:
4909:
4901:
4849:
4844:
4797:
4793:
4740:
4733:
4680:
4676:
4623:
4619:
4582:
4573:
4520:
4509:
4472:
4463:
4416:
4407:
4354:
4350:
4297:
4293:
4254:
4250:
4211:
4207:
4154:
4139:
4091:
4085:
4081:
4034:
4030:
3993:
3986:
3939:
3914:
3877:
3864:
3817:
3808:
3793:
3784:
3749:
3734:
3723:
3719:
3664:
3655:
3624:
3617:
3604:
3593:
3583:
3581:
3572:
3571:
3567:
3536:
3532:
3516:
3515:
3508:
3506:
3497:
3496:
3492:
3445:
3441:
3432:
3430:
3421:
3420:
3416:
3410:
3396:
3392:
3383:
3381:
3377:
3370:
3366:
3365:
3361:
3338:
3334:
3271:
3267:
3222:
3211:
3198:
3197:
3193:
3186:
3162:
3155:
3146:
3144:
3136:
3135:
3131:
3092:(7527): 431–5.
3077:
3068:
3027:
3010:
2973:
2948:
2938:
2936:
2933:"Succinic Acid"
2931:
2930:
2919:
2880:
2876:
2866:
2864:
2860:
2853:
2849:
2848:
2833:
2818:
2805:
2798:
2773:
2772:
2765:
2761:
2732:Flame retardant
2728:
2706:
2650:
2598:
2593:
2577:vascularization
2569:
2556:
2554:Gene regulation
2536:
2520:
2487:
2481:
2465:
2453:
2446:
2410:dendritic cells
2406:
2394:phospholipase C
2374:
2334:
2318:
2308:responses (see
2302:
2292:
2285:
2278:
2242:
2213:
2187:
2176:
2170:
2167:
2130:"Succinic acid"
2124:
2122:
2116:
2112:primary sources
2100:
2089:
2065:
2059:
2043:
2038:
2000:
1980:decarboxylation
1972:
1966:
1927:A. succinogenes
1923:
1917:
1912:
1911:
1910:
1903:"TCACycle_WP78"
1901:
1899:
1895:
1890:
1889:
1888:
1884:TCACycle_WP78
1883:
1878:
1877:
1876:
1870:
1869:
1868:
1867:
1863:
1793:
1792:
1789:
1787:
1784:
1782:
1779:
1777:
1774:
1772:
1769:
1767:
1764:
1762:
1759:
1757:
1754:
1752:
1749:
1747:
1744:
1742:
1739:
1737:
1734:
1732:
1729:
1727:
1724:
1722:
1719:
1717:
1714:
1712:
1709:
1707:
1704:
1702:
1699:
1697:
1694:
1692:
1689:
1687:
1684:
1682:
1679:
1677:
1674:
1672:
1669:
1667:
1664:
1662:
1659:
1657:
1654:
1652:
1649:
1647:
1644:
1642:
1639:
1637:
1634:
1632:
1629:
1627:
1624:
1622:
1619:
1617:
1614:
1612:
1609:
1607:
1604:
1602:
1599:
1597:
1594:
1592:
1589:
1587:
1584:
1582:
1579:
1577:
1574:
1572:
1569:
1567:
1564:
1562:
1559:
1557:
1554:
1552:
1549:
1547:
1544:
1542:
1539:
1537:
1534:
1532:
1529:
1527:
1524:
1522:
1519:
1517:
1514:
1512:
1509:
1507:
1504:
1502:
1499:
1497:
1494:
1492:
1489:
1487:
1484:
1482:
1479:
1477:
1474:
1471:
1467:
1362:
1325:
1316:
1306:
1301:
1253:
1245:Oversuccination
1215:
1207:
1199:tetrahydrofuran
1188:
1184:
1180:
1176:
1172:
1163:
1128:ethylene glycol
1118:, oxidation of
1104:
1065:
1061:
1052:
1048:
1044:
1040:
1036:
1032:
1028:
1024:
1020:
1015:
1005:
1001:
997:
993:
989:
985:
981:
977:
970:
966:
962:
958:
954:
950:
946:
942:
898:
894:
883:
791:
787:
783:
779:
735:
731:
725:
718:
713:
712:
711: ?)
702:
698:
694:
690:
676:
672:
668:
664:
660:
656:
652:
646:
631:
598:
587:
580:
578:
568:
481:
439:
429:
423:
417:
409:
395:
392:
387:
386:
375:
372:
371:
368:
362:
361:
358:
352:
351:
340:
322:
315:
306:
286:
273:
261:
248:
205:
185:
165:
145:
125:
112:
101:
88:
74:
72:
64:
63:
17:
12:
11:
5:
5671:
5661:
5660:
5655:
5650:
5645:
5640:
5635:
5618:
5617:
5612:
5609:
5608:
5605:
5604:
5601:
5597:
5593:
5587:
5584:
5580:
5576:
5570:
5567:
5563:
5559:
5553:
5550:
5546:
5542:
5536:
5533:
5529:
5525:
5519:
5516:
5512:
5508:
5502:
5499:
5495:
5491:
5485:
5482:
5478:
5474:
5468:
5464:
5460:
5456:
5450:
5446:
5442:
5438:
5432:
5428:
5424:
5420:
5414:
5410:
5406:
5400:
5396:
5389:
5388:
5385:
5384:
5379:
5375:
5368:
5367:
5360:
5353:
5345:
5336:
5335:
5331:
5330:
5324:2-oxoglutarate
5321:
5314:
5313:
5304:
5303:
5298:
5296:
5293:
5292:
5291:
5286:Oxalosuccinate
5283:
5276:
5275:
5266:
5265:
5257:
5254:
5253:
5252:
5244:
5237:
5236:
5227:
5226:
5222:
5216:
5213:
5212:
5211:
5202:
5195:
5194:
5185:
5184:
5177:
5174:
5171:
5170:
5169:
5161:
5154:
5153:
5152:
5150:
5147:
5146:
5143:
5137:
5136:
5133:
5130:
5123:
5115:
5114:
5105:
5098:
5097:
5090:
5088:
5085:
5084:
5076:
5075:
5074:
5066:
5059:
5058:
5053:
5049:
5047:
5046:
5038:
5037:
5036:
5028:
5021:
5020:
5013:
5011:
5008:
5007:
4999:
4998:
4997:
4989:
4982:
4981:
4976:
4973:
4972:
4964:
4963:
4962:
4954:
4947:
4946:
4945:
4943:
4938:
4927:
4920:
4919:
4914:
4911:
4910:
4900:
4899:
4892:
4885:
4877:
4871:
4870:
4865:
4860:
4855:
4848:
4847:External links
4845:
4843:
4842:
4791:
4731:
4694:(7): 771–784.
4674:
4617:
4596:(7): 4524–32.
4571:
4507:
4486:(6): 709–711.
4461:
4405:
4348:
4291:
4248:
4221:(9): 680–692.
4205:
4137:
4079:
4028:
3984:
3912:
3891:(2): 134–141.
3862:
3806:
3782:
3763:(5): 460–471.
3732:
3717:
3653:
3634:(5): 578–587.
3615:
3591:
3565:
3530:
3490:
3439:
3414:
3408:
3390:
3359:
3332:
3265:
3236:(2): 213–224.
3209:
3191:
3185:978-3527306732
3184:
3153:
3129:
3066:
3037:(5): 313–320.
3008:
2946:
2917:
2874:
2831:
2803:
2796:
2762:
2760:
2757:
2756:
2755:
2753:Oncometabolism
2750:
2745:
2740:
2734:
2727:
2724:
2705:
2702:
2682:neuroblastomas
2678:thyroid tumors
2649:
2646:
2618:interleukin-1β
2597:
2594:
2592:
2589:
2567:
2555:
2552:
2535:
2532:
2518:
2515:2-oxoglutarate
2480:
2477:
2464:
2461:
2451:
2445:
2442:
2405:
2402:
2373:
2370:
2346:stellate cells
2344:, and targets
2333:
2330:
2317:
2314:
2300:
2290:
2283:
2276:
2241:
2238:
2212:
2209:
2189:
2188:
2103:
2101:
2094:
2088:
2085:
2058:
2057:ROS production
2055:
2042:
2039:
2037:
2034:
1999:
1996:
1986:which cleaves
1965:
1962:
1916:
1913:
1909:
1908:
1892:
1891:
1880:
1879:
1794:
1472:
1398:
1397:
1396:
1395:
1393:
1392:
1391:
1390:
1389:
1388:
1360:
1330:by the enzyme
1323:
1305:
1302:
1300:
1297:
1252:
1249:
1231:1,4-Butanediol
1214:
1211:
1206:
1203:
1186:
1182:
1178:
1174:
1170:
1162:
1159:
1120:1,4-butanediol
1103:
1100:
1050:
1046:
1042:
1038:
1034:
1030:
1026:
1022:
1018:
1013:
1008:
1007:
1003:
999:
995:
991:
987:
983:
979:
975:
972:
968:
964:
960:
956:
952:
948:
944:
940:
882:
879:
852:Melas syndrome
848:Leigh syndrome
808:by the enzyme
789:
785:
781:
777:
723:
720:
719:
714:
692:
691:
687:standard state
684:
681:
680:
650:propionic acid
647:
641:
638:
637:
632:
626:
623:
622:
618:
617:
614:
608:
607:
603:
602:
599:
593:
590:
589:
585:
576:
570:
566:
556:
555:
552:
542:
541:
538:
528:
527:
524:
514:
513:
510:
500:
499:
496:
486:
485:
482:
477:
474:
473:
470:
464:
463:
460:
454:
453:
450:
444:
443:
437:
431:
430:
427:
421:
415:
410:
405:
402:
401:
397:
396:
394:
393:
390:
382:
381:
380:
377:
376:
374:
373:
369:
366:
365:
363:
359:
356:
355:
347:
346:
345:
342:
341:
339:
338:
325:
323:
311:
308:
307:
305:
304:
296:
294:
288:
287:
285:
284:
276:
274:
266:
263:
262:
260:
259:
251:
249:
244:
241:
240:
234:
226:
225:
215:
207:
206:
204:
203:
195:
193:
187:
186:
184:
183:
175:
173:
167:
166:
164:
163:
155:
153:
147:
146:
144:
143:
135:
133:
127:
126:
124:
123:
115:
113:
106:
103:
102:
100:
99:
91:
89:
84:
81:
80:
76:
75:
70:
66:
65:
61:
60:
54:
53:
49:
48:
40:
39:
31:
30:
20:Succinic acid
15:
9:
6:
4:
3:
2:
5670:
5659:
5656:
5654:
5651:
5649:
5646:
5644:
5641:
5639:
5636:
5634:
5631:
5630:
5628:
5615:
5610:
5591:
5588:
5574:
5571:
5557:
5554:
5540:
5537:
5523:
5520:
5506:
5503:
5489:
5486:
5472:
5469:
5454:
5451:
5436:
5433:
5418:
5415:
5404:
5401:
5394:
5391:
5390:
5386:
5373:
5366:
5361:
5359:
5354:
5352:
5347:
5346:
5343:
5326:
5325:
5318:
5308:
5288:
5287:
5280:
5270:
5249:
5248:
5241:
5231:
5208:
5207:
5199:
5189:
5166:
5165:
5158:
5149:
5148:
5144:
5142:
5139:
5138:
5132:NADH + H + CO
5131:
5128:
5121:
5116:
5109:
5103:
5102:
5080:
5070:
5064:
5063:
5042:
5032:
5026:
5025:
5003:
4993:
4987:
4986:
4968:
4958:
4952:
4951:
4931:
4925:
4924:
4917:
4912:
4908:
4905:
4898:
4893:
4891:
4886:
4884:
4879:
4878:
4875:
4869:
4866:
4864:
4861:
4859:
4858:Succinic Acid
4856:
4854:
4851:
4850:
4838:
4834:
4830:
4826:
4822:
4818:
4814:
4810:
4806:
4802:
4795:
4787:
4783:
4778:
4773:
4769:
4765:
4761:
4757:
4753:
4749:
4745:
4738:
4736:
4727:
4723:
4718:
4713:
4709:
4705:
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4688:Cell Research
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4578:
4576:
4567:
4563:
4558:
4553:
4549:
4545:
4541:
4537:
4534:(9): 3652–8.
4533:
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4525:
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4516:
4514:
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4503:
4499:
4494:
4489:
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4015:
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3998:
3991:
3989:
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3602:
3600:
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3504:
3500:
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3405:
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3394:
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3355:
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3347:
3343:
3336:
3328:
3324:
3319:
3314:
3310:
3306:
3301:
3296:
3292:
3288:
3285:(1): e54144.
3284:
3280:
3276:
3269:
3261:
3257:
3252:
3247:
3243:
3239:
3235:
3231:
3227:
3220:
3218:
3216:
3214:
3205:
3201:
3195:
3187:
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3177:
3173:
3169:
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3158:
3143:
3139:
3133:
3125:
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3111:
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2878:
2859:
2852:
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2840:
2838:
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2829:
2825:
2821:
2816:
2814:
2812:
2810:
2808:
2799:
2793:
2789:
2785:
2781:
2778:. Cambridge:
2777:
2770:
2768:
2763:
2754:
2751:
2749:
2746:
2744:
2741:
2738:
2735:
2733:
2730:
2729:
2723:
2721:
2716:
2711:
2701:
2699:
2695:
2691:
2687:
2683:
2679:
2675:
2671:
2667:
2663:
2662:paraganglioma
2659:
2655:
2654:tumorigenesis
2648:Tumorigenesis
2645:
2643:
2639:
2635:
2631:
2627:
2626:interleukin 6
2623:
2619:
2615:
2611:
2607:
2603:
2588:
2586:
2582:
2578:
2573:
2565:
2561:
2551:
2549:
2545:
2541:
2531:
2528:
2524:
2516:
2512:
2508:
2504:
2500:
2491:
2486:
2476:
2474:
2470:
2460:
2458:
2454:
2441:
2439:
2435:
2431:
2427:
2423:
2419:
2415:
2411:
2401:
2399:
2395:
2391:
2387:
2383:
2379:
2378:cardiomyocyte
2369:
2367:
2363:
2359:
2355:
2351:
2347:
2343:
2339:
2329:
2327:
2323:
2313:
2311:
2307:
2306:physiological
2303:
2295:
2293:
2286:
2279:
2272:
2268:
2264:
2260:
2256:
2252:
2248:
2232:
2228:
2226:
2222:
2218:
2208:
2205:
2200:
2196:
2185:
2182:
2174:
2163:
2160:
2156:
2153:
2149:
2146:
2142:
2139:
2135:
2132: –
2131:
2127:
2126:Find sources:
2120:
2114:
2113:
2109:
2104:This article
2102:
2098:
2093:
2092:
2084:
2082:
2078:
2074:
2070:
2064:
2054:
2052:
2048:
2028:
2024:
2022:
2018:
2014:
2009:
2005:
1995:
1993:
1989:
1985:
1981:
1977:
1971:
1961:
1959:
1955:
1950:
1948:
1944:
1940:
1936:
1932:
1928:
1922:
1904:
1897:
1893:
1887:
1882:
1874:
1798:
1402:
1387:
1386:
1382:
1380:
1376:
1372:
1368:
1363:
1357:
1355:
1351:
1346:
1343:
1341:
1337:
1333:
1329:
1321:
1315:
1311:
1296:
1294:
1290:
1286:
1282:
1278:
1274:
1270:
1266:
1262:
1258:
1257:food additive
1248:
1246:
1242:
1238:
1234:
1232:
1228:
1224:
1220:
1210:
1202:
1200:
1196:
1192:
1168:
1158:
1156:
1152:
1151:
1146:
1145:
1139:
1137:
1133:
1129:
1125:
1124:carbonylation
1121:
1117:
1113:
1112:hydrogenation
1109:
1099:
1096:
1092:
1059:
1054:
1016:
973:
938:
937:
936:
934:
933:diprotic acid
928:
892:
888:
878:
876:
872:
868:
863:
861:
857:
853:
849:
844:
842:
838:
834:
830:
826:
821:
819:
815:
811:
807:
803:
799:
795:
775:
771:
765:
729:
728:Succinic acid
717:
710:
705:
688:
682:
679:
678:glutaric acid
675:
671:
667:
666:tartaric acid
663:
659:
655:
651:
648:
645:
640:
639:
636:
633:
630:
625:
624:
619:
615:
613:
610:
609:
604:
600:
596:
592:
591:
584:
575:
571:
565:
561:
558:
557:
553:
551:
547:
544:
543:
539:
537:
533:
530:
529:
525:
523:
519:
516:
515:
511:
509:
505:
502:
501:
497:
495:
491:
488:
487:
483:
480:
476:
475:
471:
469:
468:Boiling point
466:
465:
461:
459:
458:Melting point
456:
455:
451:
449:
446:
445:
438:
436:
433:
432:
411:
408:
404:
403:
398:
389:
388:
385:
378:
364:
354:
353:
350:
343:
335:
331:
330:DTXSID6023602
327:
326:
324:
314:
310:
309:
302:
298:
297:
295:
293:
290:
289:
282:
278:
277:
275:
269:
265:
264:
257:
253:
252:
250:
247:
243:
242:
239:
235:
233:
228:
227:
223:
219:
216:
214:
212:ECHA InfoCard
209:
208:
201:
197:
196:
194:
192:
189:
188:
181:
177:
176:
174:
172:
169:
168:
161:
157:
156:
154:
152:
149:
148:
141:
137:
136:
134:
132:
129:
128:
121:
117:
116:
114:
110:
105:
104:
97:
93:
92:
90:
87:
83:
82:
77:
71:Succinic acid
67:
59:
55:
50:
46:
41:
37:
32:
28:
23:
5416:
5322:
5284:
5245:
5203:
5162:
5101:Succinyl-CoA
5099:
5060:
5022:
4983:
4950:Oxaloacetate
4948:
4921:
4804:
4800:
4794:
4751:
4747:
4691:
4687:
4677:
4634:
4630:
4620:
4593:
4589:
4531:
4527:
4483:
4479:
4423:
4419:
4365:
4361:
4351:
4311:(1): 53–58.
4308:
4304:
4294:
4264:(1): 45–58.
4261:
4257:
4251:
4218:
4214:
4208:
4165:
4161:
4099:
4095:
4082:
4045:
4041:
4031:
4004:
4000:
3950:
3946:
3888:
3884:
3828:
3824:
3800:
3760:
3756:
3726:
3720:
3675:
3671:
3631:
3627:
3609:Biochemistry
3608:
3582:. Retrieved
3578:the original
3568:
3543:
3539:
3533:
3507:. Retrieved
3502:
3493:
3456:
3452:
3442:
3431:. Retrieved
3426:
3417:
3399:
3393:
3382:. Retrieved
3362:
3345:
3341:
3335:
3282:
3278:
3268:
3233:
3229:
3204:the original
3194:
3165:
3145:. Retrieved
3141:
3132:
3089:
3085:
3034:
3030:
2984:
2980:
2937:. Retrieved
2890:(1): 19–26.
2887:
2883:
2877:
2865:. Retrieved
2858:the original
2775:
2737:Oil of amber
2707:
2674:renal tumors
2651:
2602:inflammation
2599:
2596:Inflammation
2581:angiogenesis
2557:
2537:
2503:demethylases
2496:
2469:macula densa
2466:
2447:
2407:
2375:
2335:
2319:
2296:
2258:
2243:
2214:
2211:Transporters
2192:
2177:
2168:
2158:
2151:
2144:
2137:
2125:
2105:
2066:
2051:intermediate
2047:mitochondria
2044:
2001:
1973:
1951:
1939:oxaloacetate
1934:
1930:
1926:
1924:
1896:
1384:
1383:
1364:
1358:
1347:
1344:
1328:succinyl-CoA
1317:
1299:Biosynthesis
1254:
1244:
1240:
1235:
1227:alkyd resins
1216:
1208:
1205:Applications
1167:fumaric acid
1164:
1148:
1142:
1140:
1105:
1097:
1055:
1009:
884:
870:
864:
860:inflammation
845:
825:mitochondria
822:
797:
727:
726:
674:valeric acid
670:fumaric acid
658:butyric acid
654:malonic acid
582:
573:
563:
79:Identifiers
69:Other names
4754:: 175–181.
4480:Cancer Cell
4183:2268/194560
4116:2268/194560
4042:Metabolites
2720:drug target
2614:macrophages
2485:Dioxygenase
2382:hypertrophy
2350:homeostasis
2342:hepatocytes
2255:amino acids
1241:succination
1116:maleic acid
612:Flash point
400:Properties
218:100.003.402
140:CHEBI:15741
5648:Succinates
5643:Excipients
5627:Categories
5258:NAD(P)H +
5247:Isocitrate
4923:Acetyl-CoA
4048:(7): 651.
3678:: 538790.
3584:7 November
3546:(5): 545.
3433:2015-11-18
3384:2013-11-12
3147:2017-03-09
3052:2262/67833
2867:7 November
2759:References
2748:Metabolite
2606:HIF1-alpha
2585:metabolism
2483:See also:
2414:chemotaxis
2322:adipocytes
2271:G proteins
2171:March 2017
2141:newspapers
2108:references
2075:(RET). If
2061:See also:
1998:GABA shunt
1992:glyoxylate
1988:isocitrate
1968:See also:
1919:See also:
1375:ubiquinone
1308:See also:
1223:polyesters
873:, meaning
841:metabolism
833:epigenetic
662:malic acid
554:8.8 mg/mL
546:Solubility
532:Solubility
518:Solubility
504:Solubility
498:158 mg/mL
490:Solubility
452:1.56 g/cm
435:Molar mass
301:AB6MNQ6J6L
246:IUPHAR/BPS
171:ChemSpider
107:3D model (
86:CAS Number
5206:Aconitate
5062:Succinate
4821:0950-9232
4768:0891-5849
4708:1001-0602
4651:0028-0836
4548:0021-9738
4382:0890-9369
4325:0031-6768
4286:227522279
4243:236097682
4168:: 56–65.
4102:: 56–65.
3694:2314-6133
3453:Molecules
3309:1932-6203
2904:0928-0987
2715:apoptotic
2638:glutamine
2610:cytokines
2583:, energy
2426:TNF alpha
2358:Autocrine
2338:paracrine
2326:lipolysis
1277:excipient
1237:Acylation
1219:precursor
1095:) group.
990:) → (CH
856:malignant
798:succinate
772:with the
540:50 mg/mL
526:27 mg/mL
512:54 mg/mL
160:ChEMBL576
5024:Fumarate
4837:26263513
4829:16892081
4801:Oncogene
4786:27117029
4726:26045163
4669:23535595
4612:17182618
4566:23999438
4502:23763995
4448:15901537
4400:22677546
4343:22729752
4278:33279412
4235:34301438
4200:24982373
4192:26808164
4132:24982373
4124:26808164
4074:35888775
4023:21771581
3979:26759054
3907:27194563
3857:22649411
3777:26935843
3712:23691505
3648:23333272
3560:38868987
3519:cite web
3485:19924045
3375:Archived
3327:23349810
3279:PLOS ONE
3260:21932253
3124:25383517
3061:24361092
3003:26971832
2912:16246535
2726:See also
2694:fumarate
2424:such as
2368:(VEGF).
2251:receptor
1947:fumarate
1354:fumarate
1221:to some
1033:) and Na
931:). As a
871:succinum
827:via the
806:fumarate
768:) is a
642:Related
606:Hazards
597:(χ)
536:Glycerol
494:Methanol
231:E number
191:DrugBank
96:110-15-6
5260:
5164:Citrate
4974:NADH +H
4777:5145802
4717:4493277
4660:4031686
4557:3754247
4456:8568103
4428:Bibcode
4391:3387660
4334:4574624
4065:9325148
3970:4709936
3848:3355999
3703:3652112
3509:9 March
3476:6255442
3318:3549990
3287:Bibcode
3251:3517001
3115:4255242
3094:Bibcode
2826:of the
2822:in the
2820:Record
2438:T-cells
2204:hypoxia
2155:scholar
1956:or the
1394:[[File:
1267:by the
1155:glucose
1058:radical
971:) + H
955:→ (CH
891:ionizes
837:hormone
709:what is
707: (
560:Acidity
522:Acetone
508:Ethanol
448:Density
440:118.088
268:PubChem
200:DB00139
5378:C-R-CO
5294:
5255:NAD(P)
5223:
5172:
5009:
4985:Malate
4835:
4827:
4819:
4784:
4774:
4766:
4724:
4714:
4706:
4667:
4657:
4649:
4631:Nature
4610:
4564:
4554:
4546:
4500:
4454:
4446:
4398:
4388:
4380:
4341:
4331:
4323:
4284:
4276:
4241:
4233:
4198:
4190:
4130:
4122:
4072:
4062:
4021:
3977:
3967:
3905:
3855:
3845:
3831:: 22.
3775:
3710:
3700:
3692:
3646:
3558:
3483:
3473:
3406:
3348:: 66.
3325:
3315:
3307:
3258:
3248:
3182:
3122:
3112:
3086:Nature
3059:
3001:
2939:28 May
2910:
2902:
2794:
2390:ERK1/2
2386:MEK1/2
2247:SUCNR1
2221:porins
2157:
2150:
2143:
2136:
2128:
1943:malate
1132:butane
1122:, and
850:, and
704:verify
701:
629:anions
627:Other
588:= 5.6
384:SMILES
151:ChEMBL
52:Names
4833:S2CID
4452:S2CID
4282:S2CID
4239:S2CID
4196:S2CID
4128:S2CID
4092:(PDF)
3953:: 3.
3556:S2CID
3378:(PDF)
3371:(PDF)
2861:(PDF)
2854:(PDF)
2259:GPR91
2162:JSTOR
2148:books
1334:in a
1255:As a
1108:amber
1056:As a
1029:H)(CO
986:H)(CO
967:H)(CO
875:amber
794:anion
579:= 4.2
550:Ether
349:InChI
236:E363
131:ChEBI
109:JSmol
5204:cis-
5145:NAD
5048:FADH
4825:PMID
4817:ISSN
4782:PMID
4764:ISSN
4722:PMID
4704:ISSN
4665:PMID
4647:ISSN
4608:PMID
4562:PMID
4544:ISSN
4498:PMID
4444:PMID
4396:PMID
4378:ISSN
4339:PMID
4321:ISSN
4274:PMID
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