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5052:
4978:
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5013:
5241:
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5199:
2038:
2501:
5138:
5131:
2064:. 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.
47:
345:
233:
56:
2242:
38:
5328:
4941:
2108:
5251:
5003:
706:
1244:(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.
2728:
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
2255:
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
3090:
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;
2217:
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,
2245:
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
2212:
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,
2540:
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
2585:
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
2041:
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;
2536:. 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.
5290:
5209:
5119:
5042:
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2838:
1989:, 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
2703:. 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,
1960:. 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.
5080:
3584:
2021:
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
2042:
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
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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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1846:
1826:
1822:
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1450:
1430:
1426:
2581:. 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
1856:
1460:
2723:
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
2204:
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
2226:
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
3588:
4429:
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".
5012:
2861:
2315:(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
1808:
1412:
5240:
2234:, 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
5317:
5198:
2034:(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.
2561:(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
1859:
1850:
1820:
1819:
1815:
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1454:
1424:
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2524:. 2-oxoglutarate-dependent dioxygenases require an iron cofactor to catalyze hydroxylations, desaturations and ring closures. Simultaneous to substrate oxidation, they convert
5359:
2230:, primarily SLC25A10, a succinate-fumarate/malate transporter. In the second step of mitochondrial export, succinate readily crosses the outer mitochondrial membrane through
2623:. For dendritic cells, succinate functions as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production. In inflammatory
3434:"1,4-Butanediol (BDO) Market Analysis By Application (Tetrahydrofuran, Polybutylene Teraphthalate, Gamma-Butyrolactone & Polyurethanes), And Segment Forecasts To 2020"
2643:
induces a metabolic shift towards glycolysis. In spite of a general downregulation of the TCA cycle under these conditions, succinate concentration is increased. However,
719:
3177:
4267:
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".
2082:(ROS) production by directing electron flow in the electron transport chain. Under conditions of succinate accumulation, rapid oxidation of succinate by SDH can drive
3509:
3637:
Dröse, Stefan (2013-05-01). "Differential effects of complex II on mitochondrial ROS production and their relation to cardioprotective pre- and postconditioning".
3210:
4597:"Inhibition of hypoxia-inducible factor (HIF) hydroxylases by citric acid cycle intermediates: possible links between cell metabolism and stabilization of HIF"
2893:
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".
2272:
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'
842:. Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating
394:
4224:
Fernández-Veledo S, Ceperuelo-Mallafré V, Vendrell J (September 2021). "Rethinking succinate: an unexpected hormone-like metabolite in energy homeostasis".
2090:
is unable to accommodate excess electrons supplied by succinate oxidation, it forces electrons to flow backwards along the electron transport chain. RET at
4905:
2696:
2509:
2246:(grey=nonpolar, cyan=negative charge, dark blue = positive charge, green=aromatic, dark purple=polar and noncharged, orange/light purple = special cases).
1963:
Accumulation of fumarate can drive the reverse activity of SDH, thus enhancing succinate generation. Under pathological and physiological conditions, the
1286:
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
4369:"Inhibition of α-KG-dependent histone and DNA demethylases by fumarate and succinate that are accumulated in mutations of FH and SDH tumor suppressors"
2663:
Succinate is one of three oncometabolites, metabolic intermediates whose accumulation causes metabolic and non-metabolic dysregulation implicated in
1823:
1427:
2868:
1392:
and three 2Fe-2S clusters. Succinate thus serves as a direct electron donor to the electron transport chain, and itself is converted into fumarate.
4810:
King, A.; Selak, M. A.; Gottlieb, E. (2006-01-01). "Succinate dehydrogenase and fumarate hydratase: linking mitochondrial dysfunction and cancer".
2586:
HIF1-dependent genes even under normal oxygen conditions. HIF1 is known to induce transcription of more than 60 genes, including genes involved in
2087:
2619:
or GPR91 signaling in innate immune cells. Through these mechanisms, succinate accumulation has been shown to regulate production of inflammatory
1838:
1442:
5366:
3418:
2806:
2017:(GABA) shunt into the TCA cycle, a closed cycle which synthesizes and recycles GABA. The GABA shunt serves as an alternate route to convert
5643:
3549:
Zeikus, J. G.; Jain, M. K.; Elankovan, P. (1999). "Biotechnology of succinic acid production and markets for derived industrial products".
1854:
1841:
1827:
1458:
1445:
1431:
2627:, succinate-induced stability of HIF1 results in increased transcription of HIF1-dependent genes, including the pro-inflammatory cytokine
2094:, the complex normally preceding SDH in the electron transport chain, leads to ROS production and creates a pro-oxidant microenvironment.
2031:
1857:
1461:
3194:
2558:
2376:
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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).
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2470:
is debated. Multiple studies have demonstrated succinate-induced aggregation, but the effect has high inter-individual variability.
2191:
1279:
359:
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2550:
2218:
succinate links TCA cycle dysfunction or metabolic changes to cell-cell communication and to oxidative stress-related responses.
1843:
1447:
4367:
Xiao, Mengtao; Yang, Hui; Xu, Wei; Ma, Shenghong; Lin, Huaipeng; Zhu, Honguang; Liu, Lixia; Liu, Ying; Yang, Chen (2012-06-15).
3952:
de Castro
Fonseca, Matheus; Aguiar, Carla J.; da Rocha Franco, Joao Antônio; Gingold, Rafael N.; Leite, M. Fatima (2016-01-01).
2541:
succinate load can lead to changes in transcription factor activity and genome-wide alterations in histone and DNA methylation.
1864:
1836:
1811:
1468:
1440:
1415:
4898:
4863:
3379:"Top Value Added Chemicals from Biomass, Volume 1: Results of Screening for Potential Candidates from Sugars and Synthesis Gas"
2699:. Inhibition of KDMs and TET hydroxylases results in epigenetic dysregulation and hypermethylation affecting genes involved in
2517:
2091:
1849:
1812:
1453:
1416:
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2129:
2122:
1384:. This enzyme complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of
1342:
266:
3460:"Design and Applications of Biodegradable Polyester Tissue Scaffolds Based on Endogenous Monomers Found in Human Metabolism"
2172:
2486:
via GPR91. Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.
2238:(I'm not dead yet), a sodium-independent anion exchanger, which moves both dicarboxylate and citrate into the bloodstream.
2037:
857:
Dysregulation of succinate synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as
2144:
1851:
1816:
1455:
1420:
1028:
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
2078:
The activity of succinate dehydrogenase (SDH), which interconverts succinate into fumarate participates in mitochondrial
3284:
Otero, José Manuel; Cimini, Donatella; Patil, Kiran R.; Poulsen, Simon G.; Olsson, Lisbeth; Nielsen, Jens (2013-01-21).
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1813:
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via GPR91. This leads to stellate cell activation and fibrogenesis. Thus, succinate is thought to play a role in liver
1835:
1439:
5663:
5648:
5624:
2436:
1936:
Succinate can alternatively be formed by reverse activity of SDH. Under anaerobic conditions certain bacteria such as
1865:
1818:
1469:
1422:
1389:
1290:
in pharmaceutical products, it is also used to control acidity or as a counter ion. Drugs involving succinate include
323:
3762:
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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130:
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2655:. 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
3890:
Pell, Victoria R.; Chouchani, Edward T.; Frezza, Christian; Murphy, Michael P.; Krieg, Thomas (2016-07-15).
3832:"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
228:
46:
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2444:
2140:
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1350:
1346:
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Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes.
828:
812:
2577:. PHDs hydroxylate proline in parallel to oxidatively decarboxylating 2-oxyglutarate to succinate and CO
2364:
2347:
Succinate signaling often occurs in response to hypoxic conditions. In the liver, succinate serves as a
2027:
1229:
4868:
2695:. The oncogenic mechanism caused by mutated SHD is thought to relate to succinate's ability to inhibit
2711:
have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms.
170:
4438:
3297:
3104:
2483:
2391:
viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte
2368:
2348:
1299:
1208:. Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and
1149:. Global production is estimated at 16,000 to 30,000 tons a year, with an annual growth rate of 10%.
68:
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5653:
4595:
Koivunen, P; Hirsilä, M; Remes, AM; Hassinen, IE; Kivirikko, KI; Myllyharju, J (16 February 2007).
2787:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
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3286:"Industrial Systems Biology of Saccharomyces cerevisiae Enables Novel Succinic Acid Cell Factory"
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2988:"Succinate, an intermediate in metabolism, signal transduction, ROS, hypoxia, and tumorigenesis"
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Mills, Evanna; O'Neill, Luke A.J. (May 2014). "Succinate: a metabolic signal in inflammation".
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780:
1948:, 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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3093:"Ischaemic accumulation of succinate controls reperfusion injury through mitochondrial ROS"
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2404:
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sub-type of receptor that, depending on the cell type bearing it, interacts with multiple
2231:
1990:
1209:
1138:
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190:
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Peti-Peterdi, János; Gevorgyan, Haykanush; Lam, Lisa; Riquier-Brison, Anne (2012-06-23).
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2679:, cause pathological increase in succinate. SDH mutations have also been identified in
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2002:
1998:
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2005:. 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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1971:
can increase mitochondrial fumarate, which is then readily converted to succinate.
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Gilissen, Julie; Jouret, François; Pirotte, Bernard; Hanson, Julien (2016-03-01).
3892:"Succinate metabolism: a new therapeutic target for myocardial reperfusion injury"
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Succinate serves as a modulator of blood pressure by stimulating renin release in
1333:, a primary metabolic pathway used to produce chemical energy in the presence of O
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4024:
4007:
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3004:
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2395:. Stimulation of GPR91 triggers at least two signaling pathways in the heart: a
2392:
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2235:
2205:
2107:
1303:
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1237:
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622:
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4695:"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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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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4755:"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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1807:
1411:
1064:. In living organisms, primarily succinate, not succinic acid, is found.
5034:
3908:
2631:. Other inflammatory cytokines produced by activated macrophages such as
2620:
2467:
2227:
546:
504:
248:
240:
201:
4653:
3116:
210:
5174:
4710:
4193:
4126:
1165:
847:
831:, and as a signaling molecule reflecting the cellular metabolic state.
532:
518:
458:
278:
17:
3764:"Intermediates of Metabolism: From Bystanders to Signalling Molecules"
3062:
4995:
4550:
3677:
Cheng, Ke-Ke; Wang, Gen-Yu; Zeng, Jing; Zhang, Jian-An (2013-04-18).
2986:
Tretter, Laszlo; Patocs, Attila; Chinopoulos, Christos (2016-08-01).
2508:
Accumulation of either fumarate or succinate reduces the activity of
2448:
2396:
2320:
2257:
1142:
161:
4006:
Bardella, Chiara; Pollard, Patrick J.; Tomlinson, Ian (2011-11-01).
3585:"Overview of pharmaceutical excipients used in tablets and capsules"
2305:. This enables GPR91 to regulate a multitude of signaling outcomes.
854:, especially ATP formation, to the regulation of cellular function.
696:
Except where otherwise noted, data are given for materials in their
3641:. Respiratory complex II: Role in cellular physiology and disease.
2616:
2574:
2460:
2400:
1118:
946:, succinic acid undergoes two successive deprotonation reactions:
885:
804:
560:
141:
129:
119:
4049:"Succinate as a New Actor in Pluripotency and Early Development?"
2268:
although a few studies have detected a 334 amino acid product of
4874:
Calculator: Water and solute activities in aqueous succinic acid
3516:. 31 October 2015. Archived from the original on 31 October 2017
2309:
5355:
4887:
4533:
Yang, Ming; Soga, Tomoyoshi; Pollard, Patrick J. (2013-09-03).
3810:. In Siegel, GJ; Agranoff, BW; Albers, RW; et al. (eds.).
2946:. Toxnet National Library of Medicine HSDB Database. 2005-01-31
1164:
are proposed for the commercial production via fermentation of
865:, and degradation can lead to pathological conditions, such as
3351:
Fieser, Louis F.; Martin, E. L. (1932). "Succinic
Anhydride".
3091:
Work, LM; Frezza, C; Krieg, T; Murphy, MP (20 November 2014).
2785:"CHAPTER P-6. Applications to Specific Classes of Compounds".
2276:
with its binding site facing the extracellular space. It is a
2101:
1098:
901:
639:
3954:"GPR91: expanding the frontiers of Krebs cycle intermediates"
3812:
2532:. 2-oxoglutarate-dependent dioxygenases bind substrates in a
4638:"Succinate is a danger signal that induces IL-1β via HIF-1α"
3801:
3799:
3797:
1806:
1410:
328:
3175:
Boy
Cornils; Peter Lappe. "Dicarboxylic Acids, Aliphatic".
2611:
Metabolic signaling involving succinate can be involved in
2335:, the succinate-activated GPR91 signaling cascade inhibits
2060:
and its primary biological function is that of a metabolic
1911:
The interactive pathway map can be edited at WikiPathways:
931:
803:. In living organisms, succinic acid takes the form of an
750:
3587:. Modern Medicine Network. 24 October 2008. Archived from
2528:, also known as alpha-ketoglutarate, into succinate and CO
2403:
pathway that activates hypertrophic gene expression and a
2375:, triggering the activation of angiogenic factors such as
4535:"Oncometabolites: linking altered metabolism with cancer"
1258:
occurs when more than one succinate adds to a substrate.
1180:
or be converted to diesters, such as diethylsuccinate (CH
1092:
1083:
925:
916:
768:
762:
4098:
Gilissen J, Jouret F, Pirotte B, Hanson J (March 2016).
3679:"Improved Succinate Production by Metabolic Engineering"
3085:
3083:
3081:
714:
368:
InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
4748:
4746:
3458:
Barrett, Devin G.; Yousaf, Muhammad N. (2009-10-12).
2994:. EBEC 2016: 19th European Bioenergetics Conference.
1095:
1089:
1086:
1080:
928:
922:
919:
913:
771:
765:
759:
753:
747:
378:
InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
241:
4753:
Sciacovelli, Marco; Frezza, Christian (2017-03-06).
4169:"Insight into SUCNR1 (GPR91) structure and function"
4100:"Insight into SUCNR1 (GPR91) structure and function"
3211:"NNFCC Renewable Chemicals Factsheet: Succinic Acid"
934:
4012:
Biochimica et Biophysica Acta (BBA) - Bioenergetics
3639:
Biochimica et Biophysica Acta (BBA) - Bioenergetics
2992:
Biochimica et Biophysica Acta (BBA) - Bioenergetics
2667:. Loss-of-function mutations in the genes encoding
2647:involved in the activation of macrophages increase
1077:
910:
850:-like signaling. As such, succinate links cellular
756:
265:
4590:
4588:
4586:
4480:
4478:
4476:
4424:
4422:
4420:
4162:
4160:
4158:
4156:
4154:
4152:
4001:
3999:
3947:
2208:. Alternative, succinate can be released into the
473:184–190 °C (363–374 °F; 457–463 K)
3945:
3943:
3941:
3939:
3937:
3935:
3933:
3931:
3929:
3927:
3612:
3610:
3608:
3606:
3230:
3228:
3226:
3224:
2981:
2559:JmjC domain-containing histone lysine demethylase
2308:Succinate has a high affinity for GPR91, with an
4485:Yang, Ming; Pollard, Patrick J. (10 June 2013).
3534:: CS1 maint: bot: original URL status unknown (
2979:
2977:
2975:
2973:
2971:
2969:
2967:
2965:
2963:
2961:
2030:. Finally, succinic semialdehyde is oxidized by
1356:Succinyl-CoA + NDP + Pi → Succinate + CoA + NTP
290:
4316:Pflügers Archiv: European Journal of Physiology
3825:
3823:
3821:
3814:(6th ed.). Philadelphia: Lippincott-Raven.
3672:
3670:
3668:
3632:
3630:
3384:. U.S. Department of Energy. November 1, 2004.
1810:
1414:
105:
4528:
4526:
4524:
4522:
3885:
3883:
3881:
3879:
3877:
3757:
3755:
3753:
3751:
3749:
3747:
3178:Ullmann's Encyclopedia of Industrial Chemistry
3035:
3033:
3031:
3029:
3027:
3025:
3023:
2056:Succinate is produced and concentrated in the
1117:Historically, succinic acid was obtained from
5367:
4899:
3806:Olsen, Richard W; DeLorey, Timothy M (1999).
1363:(SDH), succinate is subsequently oxidized to
8:
4693:Kelly, Beth; O'Neill, Luke AJ (2015-07-01).
3411:Ashford's Dictionary of Industrial Chemicals
2839:Institute for Occupational Safety and Health
2520:and collagen prolyl-4-hydroxylases, through
2466:, though the role of succinate signaling in
4879:PubChem: Compound Summary for Succinic Acid
2895:European Journal of Pharmaceutical Sciences
2780:
2778:
2573:(PHDs) stabilizes the transcription factor
1376:SDH also participates in the mitochondrial
1224:Precursor to polymers, resins, and solvents
1200:. This diethyl ester is a substrate in the
876:Succinic acid is marketed as food additive
811:, which has multiple biological roles as a
5374:
5360:
5352:
4906:
4892:
4884:
3617:Berg, JM; Tymoczko, JL; Stryer, L (2002).
3413:(3rd ed.), Wavelength, p. 1517,
3237:"Succinate production in Escherichia coli"
3170:
3168:
2862:"Product Information Sheet: Succinic Acid"
2363:. In the retina, succinate accumulates in
343:
231:
189:
29:
4786:
4726:
4669:
4612:
4566:
4502:
4400:
4343:
4192:
4074:
4064:
4023:
3979:
3969:
3907:
3857:
3847:
3712:
3694:
3510:"Succinic acid in the FDA SCOGS Database"
3485:
3475:
3327:
3309:
3260:
3124:
3061:
3003:
2856:
2854:
2852:
2850:
2848:
2846:
2411:-dependent hypertrophic gene activation.
2192:Learn how and when to remove this message
310:
5227:
5188:
4949:
4926:
2938:
2936:
2934:
2932:
2826:
2824:
2822:
2820:
2818:
2499:
2240:
2036:
2013:Succinate is the re-entry point for the
1282:. Succinic acid is used primarily as an
2774:
2419:SUCNR1 is highly expressed on immature
1904:
1388:via the intermediate electron carriers
1329:Succinate is a key intermediate in the
1176:Succinic acid can be dehydrogenated to
904:to form its conjugate base, succinate (
399:
364:
339:
209:
4312:"Metabolic control of renin secretion"
4226:Trends in Endocrinology and Metabolism
3623:(5th ed.). New York: W H Freeman.
3551:Applied Microbiology and Biotechnology
3527:
2427:. Furthermore, SUCNR1 synergizes with
2128:Please improve this article by adding
1993:steps of the TCA cycle via the enzyme
1204:. Dehydration of succinic acid gives
627:206 °C (403 °F; 479 K)
483:235 °C (455 °F; 508 K)
222:
4539:The Journal of Clinical Investigation
2697:2-oxogluterate-dependent dioxygenases
2598:, cell survival, and tumor invasion.
2553:(ten-eleven translocation) family of
2510:2-oxoglutarate-dependent dioxygenases
2423:, where succinate binding stimulates
2371:succinate signaling promotes retinal
2206:2-oxogluterate-dependent dioxygenases
2088:mitochondrial respiratory complex III
371:Key: KDYFGRWQOYBRFD-UHFFFAOYSA-N
169:
149:
7:
4487:"Succinate: A New Epigenetic Hacker"
3808:"GABA Synthesis, Uptake and Release"
2367:in response to ischemic conditions.
5383:Linear saturated dicarboxylic acids
4771:10.1016/j.freeradbiomed.2016.04.025
4759:Free Radical Biology & Medicine
4601:The Journal of Biological Chemistry
2750:, procured by heating succinic acid
2549:Succinate and fumarate inhibit the
2092:mitochondrial respiratory complex 1
2032:succinic semialdehyde dehydrogenase
1985:Succinate is also a product of the
381:Key: KDYFGRWQOYBRFD-UHFFFAOYAC
281:
2387:Extracellular succinate regulates
1141:. Succinate is also produced from
25:
4047:Detraux D, Renard P (July 2022).
3213:. 3 February 2010. Archived from
2671:, frequently found in hereditary
1926:Reductive branch of the TCA cycle
1370:Succinate + FAD → Fumarate + FADH
1280:U.S. Food and Drug Administration
5326:
5316:
5288:
5278:
5249:
5239:
5207:
5197:
5166:
5136:
5129:
5117:
5088:
5078:
5050:
5040:
5011:
5001:
4976:
4966:
4939:
4185:10.1016/j.pharmthera.2016.01.008
4119:10.1016/j.pharmthera.2016.01.008
3958:Cell Communication and Signaling
2575:hypoxia inducible factor (HIF)1α
2106:
1073:
906:
743:
704:
429:
54:
45:
36:
4173:Pharmacology & Therapeutics
4107:Pharmacology & Therapeutics
3391:from the original on 2013-10-21
2867:. Sigma Aldrich. Archived from
2681:gastrointestinal stromal tumors
2484:juxtaglomerular apparatus cells
1071:group it is called a succinyl (
700:(at 25 °C , 100 kPa).
3768:Trends in Biochemical Sciences
2791:The Royal Society of Chemistry
2557:DNA modifying enzymes and the
2431:to increase the production of
2343:Effect on the liver and retina
1337:. Succinate is generated from
1315:Tricarboxylic acid (TCA) cycle
880:. The name derives from Latin
840:tricarboxylic acid (TCA) cycle
435:
423:
1:
3683:BioMed Research International
2321:Functions regulated by SUCNR1
2130:secondary or tertiary sources
2098:Additional biologic functions
1250:with succinic acid is called
4025:10.1016/j.bbabio.2011.07.003
3651:10.1016/j.bbabio.2013.01.004
3311:10.1371/journal.pone.0054144
3005:10.1016/j.bbabio.2016.03.012
2512:, including histone and DNA
1276:generally recognized as safe
827:which is involved in making
495:58 g/L (20 °C) or 100 mg/mL
5644:Citric acid cycle compounds
5625:Category:Dicarboxylic acids
3409:Ashford, Robert D. (2011),
2799:10.1039/9781849733069-00648
2715:Ischemia reperfusion injury
2691:, testicular seminomas and
2351:signal, released by anoxic
1262:Food and dietary supplement
846:landscape or demonstrating
5685:
3836:Frontiers in Endocrinology
3780:10.1016/j.tibs.2016.02.003
2907:10.1016/j.ejps.2005.08.013
2534:sequential, ordered manner
2493:
2278:G protein-coupled receptor
2228:dicarboxylate transporters
2084:reverse electron transport
2071:
1978:
1932:Succinic acid fermentation
1929:
1318:
834:Succinate is generated in
5622:
5584:Hexadecanedioic acid
5398:
5162:
5135:
5128:
4955:
4929:
4924:
4504:10.1016/j.ccr.2013.05.015
4328:10.1007/s00424-012-1130-y
4238:10.1016/j.tem.2021.06.003
4008:"SDH mutations in cancer"
3971:10.1186/s12964-016-0126-1
3477:10.3390/molecules14104022
3054:10.1016/j.tcb.2013.11.008
2835:GESTIS Substance Database
2538:Oxidative decarboxylation
2433:proinflammatory cytokines
2377:endothelial growth factor
1969:purine nucleotide shuttle
694:
631:
616:
410:
390:
355:
89:
79:
67:
62:
53:
44:
35:
5603:(Phelogenic acid) C
5567:Tredecanedioic acid
4281:10.1016/j.it.2020.11.004
3849:10.3389/fendo.2012.00022
3365:10.15227/orgsyn.012.0066
3187:10.1002/14356007.a08_523
3149:"Definition of SUCCINYL"
2569:Succinate inhibition of
2443:. Succinate may enhance
1965:malate-aspartate shuttle
1378:electron transport chain
1359:Catalyzed by the enzyme
1331:tricarboxylic acid cycle
1321:Tricarboxylic acid cycle
1236:and a component of some
1161:Saccharomyces cerevisiae
900:, succinic acid readily
825:electron transport chain
5669:Metabolic intermediates
5550:Dodecanedioic acid
4373:Genes & Development
3896:Cardiovascular Research
3738:Knowing and Making Wine
3736:Peynaud, Emile (1984).
3181:. Weinheim: Wiley-VCH.
3153:www.merriam-webster.com
2669:succinate dehydrogenase
2490:Intracellular signaling
2251:Extracellular signaling
2080:reactive oxygen species
2074:Reactive Oxygen Species
2015:gamma-aminobutyric acid
1380:, where it is known as
1361:succinate dehydrogenase
1343:succinyl-CoA synthetase
1325:Succinate dehydrogenase
1152:Genetically engineered
821:succinate dehydrogenase
606:Magnetic susceptibility
5482:Heptanedioic acid
5448:(Glutaric acid) C
5446:Pentanedioic acid
5430:(Succinic acid) C
5416:(Malonic acid) CH
5414:Propanedioic acid
5406:(Oxalic acid) (CO
4824:10.1038/sj.onc.1209594
4614:10.1074/jbc.M610415200
4451:10.1098/rsta.2004.1540
4385:10.1101/gad.191056.112
4066:10.3390/metabo12070651
3253:10.1002/biot.201100061
3042:Trends in Cell Biology
2522:competitive inhibition
2505:
2415:Effect on immune cells
2365:retinal ganglion cells
2247:
2117:relies excessively on
2052:Metabolic intermediate
2043:
1876:
1480:
1382:respiratory complex II
813:metabolic intermediate
5586:(Thapsic acid) C
5535:(Sebacic acid) C
5533:Decanedioic acid
5518:(Azelaic acid) C
5516:Nonanedioic acid
5501:(Suberic acid) C
5499:Octanedioic acid
5484:(Pimelic acid) C
5464:Hexanedioic acid
5428:Butanedioic acid
5404:Ethanedioic acid
5097:CoA + ATP (GTP)
3563:10.1007/s002530051431
3241:Biotechnology Journal
2793:. 2014. p. 747.
2633:tumor necrosis factor
2615:via stabilization of
2503:
2474:Effect on the kidneys
2244:
2040:
2028:succinic semialdehyde
1946:M. succiniciproducens
1942:A. succiniciproducens
1875:
1479:
1304:solifenacin succinate
1296:sumatriptan succinate
1113:Commercial production
815:being converted into
5466:(Adipic acid) C
4269:Trends in Immunology
2701:cell differentiation
2602:Role in human health
2583:ubiquitin/proteasome
2468:platelet aggregation
2327:Effect on adipocytes
2210:extracellular milieu
1882:|alt=TCACycle_WP78
1300:doxylamine succinate
1292:metoprolol succinate
823:in complex 2 of the
84:1,4-Butanedioic acid
69:Preferred IUPAC name
4654:10.1038/nature11986
4443:2005RSPTA.363..807H
3696:10.1155/2013/538790
3591:on 19 February 2012
3438:Grand View Research
3302:2013PLoSO...854144O
3117:10.1038/nature13909
3109:2014Natur.515..431C
2645:lipopolysaccharides
2641:toll-like receptors
2571:prolyl hydroxylases
2518:prolyl hydroxylases
2455:Effect on platelets
2429:toll-like receptors
2383:Effect on the heart
2284:subtypes including
2047:Cellular metabolism
2019:alpha-ketoglutarate
2001:into succinate and
1274:, succinic acid is
1228:Succinic acid is a
1202:Stobbe condensation
892:Physical properties
873:and tissue injury.
490:Solubility in water
453: g·mol
249:(antioxidants, ...)
32:
5664:E-number additives
5649:Dicarboxylic acids
5601:Docosanedioic acid
5569:(Brassylic acid) C
4711:10.1038/cr.2015.68
3909:10.1093/cvr/cvw100
2874:on 7 November 2017
2721:reperfusion injury
2709:2-hydroxyglutarate
2545:Epigenetic effects
2506:
2373:neovascularization
2248:
2044:
1877:
1481:
1272:dietary supplement
1206:succinic anhydride
1172:Chemical reactions
727:Infobox references
632:Related compounds
30:
5631:
5630:
5349:
5348:
5344:
5343:
5104:+ ADP (GDP)
4918:metabolic pathway
4915:Citric acid cycle
4818:(34): 4675–4682.
4648:(7444): 238–242.
4437:(1829): 807–828.
4379:(12): 1326–1338.
4018:(11): 1432–1443.
3514:FDA GRAS Database
3470:(10): 4022–4050.
3420:978-0-9522674-3-0
3353:Organic Syntheses
2808:978-0-85404-182-4
2754:Citric acid cycle
2653:GABA transporters
2445:adaptive immunity
2441:interleukin-1beta
2274:surface membranes
2202:
2201:
2194:
2176:
2024:GABA transaminase
1353:-producing step:
1284:acidity regulator
781:dicarboxylic acid
735:Chemical compound
733:
732:
324:CompTox Dashboard
131:Interactive image
27:Dicarboxylic acid
16:(Redirected from
5676:
5376:
5369:
5362:
5353:
5330:
5320:
5292:
5282:
5272:
5253:
5243:
5231:
5211:
5201:
5192:
5170:
5140:
5133:
5121:
5092:
5082:
5054:
5044:
5015:
5005:
4980:
4970:
4953:
4943:
4927:
4908:
4901:
4894:
4885:
4852:
4851:
4807:
4801:
4800:
4790:
4750:
4741:
4740:
4730:
4690:
4684:
4683:
4673:
4633:
4627:
4626:
4616:
4592:
4581:
4580:
4570:
4551:10.1172/JCI67228
4530:
4517:
4516:
4506:
4482:
4471:
4470:
4426:
4415:
4414:
4404:
4364:
4358:
4357:
4347:
4307:
4301:
4300:
4264:
4258:
4257:
4221:
4215:
4214:
4196:
4164:
4147:
4146:
4104:
4095:
4089:
4088:
4078:
4068:
4044:
4038:
4037:
4027:
4003:
3994:
3993:
3983:
3973:
3949:
3922:
3921:
3911:
3887:
3872:
3871:
3861:
3851:
3827:
3816:
3815:
3803:
3792:
3791:
3759:
3742:
3741:
3733:
3727:
3726:
3716:
3698:
3674:
3663:
3662:
3634:
3625:
3624:
3614:
3601:
3600:
3598:
3596:
3581:
3575:
3574:
3546:
3540:
3539:
3533:
3525:
3523:
3521:
3506:
3500:
3499:
3489:
3479:
3455:
3449:
3448:
3446:
3445:
3440:. September 2015
3430:
3424:
3423:
3406:
3400:
3399:
3397:
3396:
3390:
3383:
3375:
3369:
3368:
3348:
3342:
3341:
3331:
3313:
3281:
3275:
3274:
3264:
3232:
3219:
3218:
3217:on 20 July 2011.
3207:
3201:
3200:
3172:
3163:
3162:
3160:
3159:
3145:
3139:
3138:
3128:
3087:
3076:
3075:
3065:
3037:
3018:
3017:
3007:
2998:(8): 1086–1101.
2983:
2956:
2955:
2953:
2951:
2940:
2927:
2926:
2890:
2884:
2883:
2881:
2879:
2873:
2866:
2858:
2841:
2828:
2813:
2812:
2782:
2677:pheochromocytoma
2555:5-methylcytosine
2197:
2190:
2186:
2183:
2177:
2175:
2134:
2110:
2102:
1995:isocitrate lyase
1987:glyoxylate cycle
1981:Glyoxylate cycle
1975:Glyoxylate cycle
1918:
1917:
1909:
1802:
1797:
1792:
1787:
1782:
1777:
1772:
1767:
1762:
1757:
1752:
1747:
1742:
1737:
1732:
1727:
1722:
1717:
1712:
1707:
1702:
1697:
1692:
1687:
1682:
1677:
1672:
1667:
1662:
1657:
1652:
1647:
1642:
1637:
1632:
1627:
1622:
1617:
1612:
1607:
1602:
1597:
1592:
1587:
1582:
1577:
1572:
1567:
1562:
1557:
1552:
1547:
1542:
1537:
1532:
1527:
1522:
1517:
1512:
1507:
1502:
1497:
1492:
1487:
1155:Escherichia coli
1147:maleic anhydride
1105:
1104:
1101:
1100:
1097:
1094:
1091:
1088:
1085:
1082:
1079:
941:
940:
937:
936:
933:
930:
927:
924:
921:
918:
915:
912:
898:aqueous solution
869:transformation,
785:chemical formula
778:
777:
774:
773:
770:
767:
764:
761:
758:
755:
752:
749:
717:
711:
708:
707:
655:carboxylic acids
646:sodium succinate
612:-57.9·10 cm/mol
452:
437:
431:
425:
418:Chemical formula
402:C(CC(=O)O)C(=O)O
348:
347:
332:
330:
314:
294:
283:
269:
243:
235:
224:
213:
193:
173:
153:
133:
109:
73:Butanedioic acid
58:
49:
40:
33:
21:
5684:
5683:
5679:
5678:
5677:
5675:
5674:
5673:
5634:
5633:
5632:
5627:
5618:
5617:
5614:
5610:
5606:
5597:
5593:
5589:
5580:
5576:
5572:
5563:
5559:
5555:
5546:
5542:
5538:
5529:
5525:
5521:
5512:
5508:
5504:
5495:
5491:
5487:
5477:
5473:
5469:
5459:
5455:
5451:
5441:
5437:
5433:
5423:
5419:
5409:
5394:
5392:
5388:
5380:
5350:
5345:
5340:
5339:
5338:
5331:
5323:
5322:
5321:
5313:
5312:
5311:
5306:
5301:
5300:
5293:
5285:
5284:
5283:
5275:
5274:
5270:
5267:
5262:
5261:
5254:
5246:
5245:
5244:
5236:
5235:
5232:
5229:
5225:
5221:
5220:
5212:
5204:
5203:
5202:
5194:
5193:
5190:
5186:
5184:
5179:
5178:
5171:
5146:
5124:
5123:
5122:
5115:
5107:
5106:
5105:
5103:
5098:
5094:
5093:
5084:
5083:
5076:
5068:
5067:
5066:
5063:
5062:
5056:
5055:
5046:
5045:
5038:
5030:
5029:
5028:
5026:
5021:
5017:
5016:
5007:
5006:
4999:
4991:
4990:
4989:
4986:
4982:
4981:
4972:
4971:
4964:
4951:
4947:
4945:
4944:
4937:
4920:
4912:
4860:
4855:
4809:
4808:
4804:
4752:
4751:
4744:
4692:
4691:
4687:
4635:
4634:
4630:
4594:
4593:
4584:
4532:
4531:
4520:
4484:
4483:
4474:
4428:
4427:
4418:
4366:
4365:
4361:
4309:
4308:
4304:
4266:
4265:
4261:
4223:
4222:
4218:
4166:
4165:
4150:
4102:
4097:
4096:
4092:
4046:
4045:
4041:
4005:
4004:
3997:
3951:
3950:
3925:
3889:
3888:
3875:
3829:
3828:
3819:
3805:
3804:
3795:
3761:
3760:
3745:
3735:
3734:
3730:
3676:
3675:
3666:
3636:
3635:
3628:
3616:
3615:
3604:
3594:
3592:
3583:
3582:
3578:
3548:
3547:
3543:
3526:
3519:
3517:
3508:
3507:
3503:
3457:
3456:
3452:
3443:
3441:
3432:
3431:
3427:
3421:
3408:
3407:
3403:
3394:
3392:
3388:
3381:
3377:
3376:
3372:
3350:
3349:
3345:
3283:
3282:
3278:
3234:
3233:
3222:
3209:
3208:
3204:
3197:
3174:
3173:
3166:
3157:
3155:
3147:
3146:
3142:
3103:(7527): 431–5.
3089:
3088:
3079:
3039:
3038:
3021:
2985:
2984:
2959:
2949:
2947:
2944:"Succinic Acid"
2942:
2941:
2930:
2892:
2891:
2887:
2877:
2875:
2871:
2864:
2860:
2859:
2844:
2829:
2816:
2809:
2784:
2783:
2776:
2772:
2743:Flame retardant
2739:
2717:
2661:
2609:
2604:
2588:vascularization
2580:
2567:
2565:Gene regulation
2547:
2531:
2498:
2492:
2476:
2464:
2457:
2421:dendritic cells
2417:
2405:phospholipase C
2385:
2345:
2329:
2319:responses (see
2313:
2303:
2296:
2289:
2253:
2224:
2198:
2187:
2181:
2178:
2141:"Succinic acid"
2135:
2133:
2127:
2123:primary sources
2111:
2100:
2076:
2070:
2054:
2049:
2011:
1991:decarboxylation
1983:
1977:
1938:A. succinogenes
1934:
1928:
1923:
1922:
1921:
1914:"TCACycle_WP78"
1912:
1910:
1906:
1901:
1900:
1899:
1895:TCACycle_WP78
1894:
1889:
1888:
1887:
1881:
1880:
1879:
1878:
1874:
1804:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1770:
1768:
1765:
1763:
1760:
1758:
1755:
1753:
1750:
1748:
1745:
1743:
1740:
1738:
1735:
1733:
1730:
1728:
1725:
1723:
1720:
1718:
1715:
1713:
1710:
1708:
1705:
1703:
1700:
1698:
1695:
1693:
1690:
1688:
1685:
1683:
1680:
1678:
1675:
1673:
1670:
1668:
1665:
1663:
1660:
1658:
1655:
1653:
1650:
1648:
1645:
1643:
1640:
1638:
1635:
1633:
1630:
1628:
1625:
1623:
1620:
1618:
1615:
1613:
1610:
1608:
1605:
1603:
1600:
1598:
1595:
1593:
1590:
1588:
1585:
1583:
1580:
1578:
1575:
1573:
1570:
1568:
1565:
1563:
1560:
1558:
1555:
1553:
1550:
1548:
1545:
1543:
1540:
1538:
1535:
1533:
1530:
1528:
1525:
1523:
1520:
1518:
1515:
1513:
1510:
1508:
1505:
1503:
1500:
1498:
1495:
1493:
1490:
1488:
1485:
1482:
1478:
1373:
1336:
1327:
1317:
1312:
1264:
1256:Oversuccination
1226:
1218:
1210:tetrahydrofuran
1199:
1195:
1191:
1187:
1183:
1174:
1139:ethylene glycol
1129:, oxidation of
1115:
1076:
1072:
1063:
1059:
1055:
1051:
1047:
1043:
1039:
1035:
1031:
1026:
1016:
1012:
1008:
1004:
1000:
996:
992:
988:
981:
977:
973:
969:
965:
961:
957:
953:
909:
905:
894:
802:
798:
794:
790:
746:
742:
736:
729:
724:
723:
722: ?)
713:
709:
705:
701:
687:
683:
679:
675:
671:
667:
663:
657:
642:
609:
598:
591:
589:
579:
492:
450:
440:
434:
428:
420:
406:
403:
398:
397:
386:
383:
382:
379:
373:
372:
369:
363:
362:
351:
333:
326:
317:
297:
284:
272:
259:
216:
196:
176:
156:
136:
123:
112:
99:
85:
83:
75:
74:
28:
23:
22:
15:
12:
11:
5:
5682:
5680:
5672:
5671:
5666:
5661:
5656:
5651:
5646:
5636:
5635:
5629:
5628:
5623:
5620:
5619:
5616:
5615:
5612:
5608:
5604:
5598:
5595:
5591:
5587:
5581:
5578:
5574:
5570:
5564:
5561:
5557:
5553:
5547:
5544:
5540:
5536:
5530:
5527:
5523:
5519:
5513:
5510:
5506:
5502:
5496:
5493:
5489:
5485:
5479:
5475:
5471:
5467:
5461:
5457:
5453:
5449:
5443:
5439:
5435:
5431:
5425:
5421:
5417:
5411:
5407:
5400:
5399:
5396:
5395:
5390:
5386:
5381:
5379:
5378:
5371:
5364:
5356:
5347:
5346:
5342:
5341:
5335:2-oxoglutarate
5332:
5325:
5324:
5315:
5314:
5309:
5307:
5304:
5303:
5302:
5297:Oxalosuccinate
5294:
5287:
5286:
5277:
5276:
5268:
5265:
5264:
5263:
5255:
5248:
5247:
5238:
5237:
5233:
5224:
5223:
5222:
5213:
5206:
5205:
5196:
5195:
5185:
5182:
5181:
5180:
5172:
5165:
5164:
5163:
5161:
5158:
5157:
5154:
5148:
5147:
5144:
5141:
5134:
5126:
5125:
5116:
5109:
5108:
5101:
5099:
5096:
5095:
5087:
5086:
5085:
5077:
5070:
5069:
5064:
5060:
5058:
5057:
5049:
5048:
5047:
5039:
5032:
5031:
5024:
5022:
5019:
5018:
5010:
5009:
5008:
5000:
4993:
4992:
4987:
4984:
4983:
4975:
4974:
4973:
4965:
4958:
4957:
4956:
4954:
4938:
4931:
4930:
4925:
4922:
4921:
4913:
4911:
4910:
4903:
4896:
4888:
4882:
4881:
4876:
4871:
4866:
4859:
4858:External links
4856:
4854:
4853:
4802:
4742:
4705:(7): 771–784.
4685:
4628:
4607:(7): 4524–32.
4582:
4518:
4497:(6): 709–711.
4472:
4416:
4359:
4302:
4259:
4232:(9): 680–692.
4216:
4148:
4090:
4039:
3995:
3923:
3902:(2): 134–141.
3873:
3817:
3793:
3774:(5): 460–471.
3743:
3728:
3664:
3645:(5): 578–587.
3626:
3602:
3576:
3541:
3501:
3450:
3425:
3419:
3401:
3370:
3343:
3276:
3247:(2): 213–224.
3220:
3202:
3196:978-3527306732
3195:
3164:
3140:
3077:
3048:(5): 313–320.
3019:
2957:
2928:
2885:
2842:
2814:
2807:
2773:
2771:
2768:
2767:
2766:
2764:Oncometabolism
2761:
2756:
2751:
2745:
2738:
2735:
2716:
2713:
2693:neuroblastomas
2689:thyroid tumors
2660:
2657:
2629:interleukin-1β
2608:
2605:
2603:
2600:
2578:
2566:
2563:
2546:
2543:
2529:
2526:2-oxoglutarate
2491:
2488:
2475:
2472:
2462:
2456:
2453:
2416:
2413:
2384:
2381:
2357:stellate cells
2355:, and targets
2344:
2341:
2328:
2325:
2311:
2301:
2294:
2287:
2252:
2249:
2223:
2220:
2200:
2199:
2114:
2112:
2105:
2099:
2096:
2069:
2068:ROS production
2066:
2053:
2050:
2048:
2045:
2010:
2007:
1997:which cleaves
1976:
1973:
1927:
1924:
1920:
1919:
1903:
1902:
1891:
1890:
1805:
1799:
1794:
1789:
1784:
1779:
1774:
1769:
1764:
1759:
1754:
1749:
1744:
1739:
1734:
1729:
1724:
1719:
1714:
1709:
1704:
1699:
1694:
1689:
1684:
1679:
1674:
1669:
1664:
1659:
1654:
1649:
1644:
1639:
1634:
1629:
1624:
1619:
1614:
1609:
1604:
1599:
1594:
1589:
1584:
1579:
1574:
1569:
1564:
1559:
1554:
1549:
1544:
1539:
1534:
1529:
1524:
1519:
1514:
1509:
1504:
1499:
1494:
1489:
1484:
1483:
1409:
1408:
1407:
1406:
1404:
1403:
1402:
1401:
1400:
1399:
1371:
1341:by the enzyme
1334:
1316:
1313:
1311:
1308:
1263:
1260:
1242:1,4-Butanediol
1225:
1222:
1217:
1214:
1197:
1193:
1189:
1185:
1181:
1173:
1170:
1131:1,4-butanediol
1114:
1111:
1061:
1057:
1053:
1049:
1045:
1041:
1037:
1033:
1029:
1024:
1019:
1018:
1014:
1010:
1006:
1002:
998:
994:
990:
986:
983:
979:
975:
971:
967:
963:
959:
955:
951:
893:
890:
863:Melas syndrome
859:Leigh syndrome
819:by the enzyme
800:
796:
792:
788:
734:
731:
730:
725:
703:
702:
698:standard state
695:
692:
691:
661:propionic acid
658:
652:
649:
648:
643:
637:
634:
633:
629:
628:
625:
619:
618:
614:
613:
610:
604:
601:
600:
596:
587:
581:
577:
567:
566:
563:
553:
552:
549:
539:
538:
535:
525:
524:
521:
511:
510:
507:
497:
496:
493:
488:
485:
484:
481:
475:
474:
471:
465:
464:
461:
455:
454:
448:
442:
441:
438:
432:
426:
421:
416:
413:
412:
408:
407:
405:
404:
401:
393:
392:
391:
388:
387:
385:
384:
380:
377:
376:
374:
370:
367:
366:
358:
357:
356:
353:
352:
350:
349:
336:
334:
322:
319:
318:
316:
315:
307:
305:
299:
298:
296:
295:
287:
285:
277:
274:
273:
271:
270:
262:
260:
255:
252:
251:
245:
237:
236:
226:
218:
217:
215:
214:
206:
204:
198:
197:
195:
194:
186:
184:
178:
177:
175:
174:
166:
164:
158:
157:
155:
154:
146:
144:
138:
137:
135:
134:
126:
124:
117:
114:
113:
111:
110:
102:
100:
95:
92:
91:
87:
86:
81:
77:
76:
72:
71:
65:
64:
60:
59:
51:
50:
42:
41:
31:Succinic acid
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
5681:
5670:
5667:
5665:
5662:
5660:
5657:
5655:
5652:
5650:
5647:
5645:
5642:
5641:
5639:
5626:
5621:
5602:
5599:
5585:
5582:
5568:
5565:
5551:
5548:
5534:
5531:
5517:
5514:
5500:
5497:
5483:
5480:
5465:
5462:
5447:
5444:
5429:
5426:
5415:
5412:
5405:
5402:
5401:
5397:
5384:
5377:
5372:
5370:
5365:
5363:
5358:
5357:
5354:
5337:
5336:
5329:
5319:
5299:
5298:
5291:
5281:
5260:
5259:
5252:
5242:
5219:
5218:
5210:
5200:
5177:
5176:
5169:
5160:
5159:
5155:
5153:
5150:
5149:
5143:NADH + H + CO
5142:
5139:
5132:
5127:
5120:
5114:
5113:
5091:
5081:
5075:
5074:
5053:
5043:
5037:
5036:
5014:
5004:
4998:
4997:
4979:
4969:
4963:
4962:
4942:
4936:
4935:
4928:
4923:
4919:
4916:
4909:
4904:
4902:
4897:
4895:
4890:
4889:
4886:
4880:
4877:
4875:
4872:
4870:
4869:Succinic Acid
4867:
4865:
4862:
4861:
4857:
4849:
4845:
4841:
4837:
4833:
4829:
4825:
4821:
4817:
4813:
4806:
4803:
4798:
4794:
4789:
4784:
4780:
4776:
4772:
4768:
4764:
4760:
4756:
4749:
4747:
4743:
4738:
4734:
4729:
4724:
4720:
4716:
4712:
4708:
4704:
4700:
4699:Cell Research
4696:
4689:
4686:
4681:
4677:
4672:
4667:
4663:
4659:
4655:
4651:
4647:
4643:
4639:
4632:
4629:
4624:
4620:
4615:
4610:
4606:
4602:
4598:
4591:
4589:
4587:
4583:
4578:
4574:
4569:
4564:
4560:
4556:
4552:
4548:
4545:(9): 3652–8.
4544:
4540:
4536:
4529:
4527:
4525:
4523:
4519:
4514:
4510:
4505:
4500:
4496:
4492:
4488:
4481:
4479:
4477:
4473:
4468:
4464:
4460:
4456:
4452:
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3307:
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3299:
3296:(1): e54144.
3295:
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2789:. Cambridge:
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2710:
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2702:
2698:
2694:
2690:
2686:
2682:
2678:
2674:
2673:paraganglioma
2670:
2666:
2665:tumorigenesis
2659:Tumorigenesis
2658:
2656:
2654:
2650:
2646:
2642:
2638:
2637:interleukin 6
2634:
2630:
2626:
2622:
2618:
2614:
2606:
2601:
2599:
2597:
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2589:
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2430:
2426:
2422:
2414:
2412:
2410:
2406:
2402:
2398:
2394:
2390:
2389:cardiomyocyte
2382:
2380:
2378:
2374:
2370:
2366:
2362:
2358:
2354:
2350:
2342:
2340:
2338:
2334:
2326:
2324:
2322:
2318:
2317:physiological
2314:
2306:
2304:
2297:
2290:
2283:
2279:
2275:
2271:
2267:
2263:
2259:
2250:
2243:
2239:
2237:
2233:
2229:
2221:
2219:
2216:
2211:
2207:
2196:
2193:
2185:
2174:
2171:
2167:
2164:
2160:
2157:
2153:
2150:
2146:
2143: –
2142:
2138:
2137:Find sources:
2131:
2125:
2124:
2120:
2115:This article
2113:
2109:
2104:
2103:
2097:
2095:
2093:
2089:
2085:
2081:
2075:
2067:
2065:
2063:
2059:
2051:
2046:
2039:
2035:
2033:
2029:
2025:
2020:
2016:
2008:
2006:
2004:
2000:
1996:
1992:
1988:
1982:
1974:
1972:
1970:
1966:
1961:
1959:
1955:
1951:
1947:
1943:
1939:
1933:
1925:
1915:
1908:
1905:
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1344:
1340:
1332:
1326:
1322:
1314:
1309:
1307:
1305:
1301:
1297:
1293:
1289:
1285:
1281:
1277:
1273:
1269:
1268:food additive
1261:
1259:
1257:
1253:
1249:
1245:
1243:
1239:
1235:
1231:
1223:
1221:
1215:
1213:
1211:
1207:
1203:
1179:
1171:
1169:
1167:
1163:
1162:
1157:
1156:
1150:
1148:
1144:
1140:
1136:
1135:carbonylation
1132:
1128:
1124:
1123:hydrogenation
1120:
1112:
1110:
1107:
1103:
1070:
1065:
1027:
984:
949:
948:
947:
945:
944:diprotic acid
939:
903:
899:
891:
889:
887:
883:
879:
874:
872:
868:
864:
860:
855:
853:
849:
845:
841:
837:
832:
830:
826:
822:
818:
814:
810:
806:
786:
782:
776:
740:
739:Succinic acid
728:
721:
716:
699:
693:
690:
689:glutaric acid
686:
682:
678:
677:tartaric acid
674:
670:
666:
662:
659:
656:
651:
650:
647:
644:
641:
636:
635:
630:
626:
624:
621:
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615:
611:
607:
603:
602:
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586:
582:
576:
572:
569:
568:
564:
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541:
540:
536:
534:
530:
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522:
520:
516:
513:
512:
508:
506:
502:
499:
498:
494:
491:
487:
486:
482:
480:
479:Boiling point
477:
476:
472:
470:
469:Melting point
467:
466:
462:
460:
457:
456:
449:
447:
444:
443:
422:
419:
415:
414:
409:
400:
396:
389:
375:
365:
361:
354:
346:
342:
341:DTXSID6023602
338:
337:
335:
325:
321:
320:
313:
309:
308:
306:
304:
301:
300:
293:
289:
288:
286:
280:
276:
275:
268:
264:
263:
261:
258:
254:
253:
250:
246:
244:
239:
238:
234:
230:
227:
225:
223:ECHA InfoCard
220:
219:
212:
208:
207:
205:
203:
200:
199:
192:
188:
187:
185:
183:
180:
179:
172:
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167:
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163:
160:
159:
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148:
147:
145:
143:
140:
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132:
128:
127:
125:
121:
116:
115:
108:
104:
103:
101:
98:
94:
93:
88:
82:Succinic acid
78:
70:
66:
61:
57:
52:
48:
43:
39:
34:
19:
5427:
5333:
5295:
5256:
5214:
5173:
5112:Succinyl-CoA
5110:
5071:
5033:
4994:
4961:Oxaloacetate
4959:
4932:
4815:
4811:
4805:
4762:
4758:
4702:
4698:
4688:
4645:
4641:
4631:
4604:
4600:
4542:
4538:
4494:
4490:
4434:
4430:
4376:
4372:
4362:
4322:(1): 53–58.
4319:
4315:
4305:
4275:(1): 45–58.
4272:
4268:
4262:
4229:
4225:
4219:
4176:
4172:
4110:
4106:
4093:
4056:
4052:
4042:
4015:
4011:
3961:
3957:
3899:
3895:
3839:
3835:
3811:
3771:
3767:
3737:
3731:
3686:
3682:
3642:
3638:
3620:Biochemistry
3619:
3593:. Retrieved
3589:the original
3579:
3554:
3550:
3544:
3518:. Retrieved
3513:
3504:
3467:
3463:
3453:
3442:. Retrieved
3437:
3428:
3410:
3404:
3393:. Retrieved
3373:
3356:
3352:
3346:
3293:
3289:
3279:
3244:
3240:
3215:the original
3205:
3176:
3156:. Retrieved
3152:
3143:
3100:
3096:
3045:
3041:
2995:
2991:
2948:. Retrieved
2901:(1): 19–26.
2898:
2894:
2888:
2876:. Retrieved
2869:the original
2786:
2748:Oil of amber
2718:
2685:renal tumors
2662:
2613:inflammation
2610:
2607:Inflammation
2592:angiogenesis
2568:
2548:
2514:demethylases
2507:
2480:macula densa
2477:
2458:
2418:
2386:
2346:
2330:
2307:
2269:
2254:
2225:
2222:Transporters
2203:
2188:
2179:
2169:
2162:
2155:
2148:
2136:
2116:
2077:
2062:intermediate
2058:mitochondria
2055:
2012:
1984:
1962:
1950:oxaloacetate
1945:
1941:
1937:
1935:
1907:
1395:
1394:
1375:
1369:
1358:
1355:
1339:succinyl-CoA
1328:
1310:Biosynthesis
1265:
1255:
1251:
1246:
1238:alkyd resins
1227:
1219:
1216:Applications
1178:fumaric acid
1175:
1159:
1153:
1151:
1116:
1108:
1066:
1020:
895:
881:
875:
871:inflammation
856:
836:mitochondria
833:
808:
738:
737:
685:valeric acid
681:fumaric acid
669:butyric acid
665:malonic acid
593:
584:
574:
90:Identifiers
80:Other names
4765:: 175–181.
4491:Cancer Cell
4194:2268/194560
4127:2268/194560
4053:Metabolites
2731:drug target
2625:macrophages
2496:Dioxygenase
2393:hypertrophy
2361:homeostasis
2353:hepatocytes
2266:amino acids
1252:succination
1127:maleic acid
623:Flash point
411:Properties
229:100.003.402
151:CHEBI:15741
5659:Succinates
5654:Excipients
5638:Categories
5269:NAD(P)H +
5258:Isocitrate
4934:Acetyl-CoA
4059:(7): 651.
3689:: 538790.
3595:7 November
3557:(5): 545.
3444:2015-11-18
3395:2013-11-12
3158:2017-03-09
3063:2262/67833
2878:7 November
2770:References
2759:Metabolite
2617:HIF1-alpha
2596:metabolism
2494:See also:
2425:chemotaxis
2333:adipocytes
2282:G proteins
2182:March 2017
2152:newspapers
2119:references
2086:(RET). If
2072:See also:
2009:GABA shunt
2003:glyoxylate
1999:isocitrate
1979:See also:
1930:See also:
1386:ubiquinone
1319:See also:
1234:polyesters
884:, meaning
852:metabolism
844:epigenetic
673:malic acid
565:8.8 mg/mL
557:Solubility
543:Solubility
529:Solubility
515:Solubility
509:158 mg/mL
501:Solubility
463:1.56 g/cm
446:Molar mass
312:AB6MNQ6J6L
257:IUPHAR/BPS
182:ChemSpider
118:3D model (
97:CAS Number
5217:Aconitate
5073:Succinate
4832:0950-9232
4779:0891-5849
4719:1001-0602
4662:0028-0836
4559:0021-9738
4393:0890-9369
4336:0031-6768
4297:227522279
4254:236097682
4179:: 56–65.
4113:: 56–65.
3705:2314-6133
3464:Molecules
3320:1932-6203
2915:0928-0987
2726:apoptotic
2649:glutamine
2621:cytokines
2594:, energy
2437:TNF alpha
2369:Autocrine
2349:paracrine
2337:lipolysis
1288:excipient
1248:Acylation
1230:precursor
1106:) group.
1001:) → (CH
867:malignant
809:succinate
783:with the
551:50 mg/mL
537:27 mg/mL
523:54 mg/mL
171:ChEMBL576
5035:Fumarate
4848:26263513
4840:16892081
4812:Oncogene
4797:27117029
4737:26045163
4680:23535595
4623:17182618
4577:23999438
4513:23763995
4459:15901537
4411:22677546
4354:22729752
4289:33279412
4246:34301438
4211:24982373
4203:26808164
4143:24982373
4135:26808164
4085:35888775
4034:21771581
3990:26759054
3918:27194563
3868:22649411
3788:26935843
3723:23691505
3659:23333272
3571:38868987
3530:cite web
3496:19924045
3386:Archived
3338:23349810
3290:PLOS ONE
3271:21932253
3135:25383517
3072:24361092
3014:26971832
2923:16246535
2737:See also
2705:fumarate
2435:such as
2379:(VEGF).
2262:receptor
1958:fumarate
1365:fumarate
1232:to some
1044:) and Na
942:). As a
882:succinum
838:via the
817:fumarate
779:) is a
653:Related
617:Hazards
608:(χ)
547:Glycerol
505:Methanol
242:E number
202:DrugBank
107:110-15-6
5271:
5175:Citrate
4985:NADH +H
4788:5145802
4728:4493277
4671:4031686
4568:3754247
4467:8568103
4439:Bibcode
4402:3387660
4345:4574624
4076:9325148
3981:4709936
3859:3355999
3714:3652112
3520:9 March
3487:6255442
3329:3549990
3298:Bibcode
3262:3517001
3126:4255242
3105:Bibcode
2837:of the
2833:in the
2831:Record
2449:T-cells
2215:hypoxia
2166:scholar
1967:or the
1405:[[File:
1278:by the
1166:glucose
1069:radical
982:) + H
966:→ (CH
902:ionizes
848:hormone
720:what is
718: (
571:Acidity
533:Acetone
519:Ethanol
459:Density
451:118.088
279:PubChem
211:DB00139
18:Amberin
5389:C-R-CO
5305:
5266:NAD(P)
5234:
5183:
5020:
4996:Malate
4846:
4838:
4830:
4795:
4785:
4777:
4735:
4725:
4717:
4678:
4668:
4660:
4642:Nature
4621:
4575:
4565:
4557:
4511:
4465:
4457:
4409:
4399:
4391:
4352:
4342:
4334:
4295:
4287:
4252:
4244:
4209:
4201:
4141:
4133:
4083:
4073:
4032:
3988:
3978:
3916:
3866:
3856:
3842:: 22.
3786:
3721:
3711:
3703:
3657:
3569:
3494:
3484:
3417:
3359:: 66.
3336:
3326:
3318:
3269:
3259:
3193:
3133:
3123:
3097:Nature
3070:
3012:
2950:28 May
2921:
2913:
2805:
2401:ERK1/2
2397:MEK1/2
2258:SUCNR1
2232:porins
2168:
2161:
2154:
2147:
2139:
1954:malate
1143:butane
1133:, and
861:, and
715:verify
712:
640:anions
638:Other
599:= 5.6
395:SMILES
162:ChEMBL
63:Names
4844:S2CID
4463:S2CID
4293:S2CID
4250:S2CID
4207:S2CID
4139:S2CID
4103:(PDF)
3964:: 3.
3567:S2CID
3389:(PDF)
3382:(PDF)
2872:(PDF)
2865:(PDF)
2270:GPR91
2173:JSTOR
2159:books
1345:in a
1266:As a
1119:amber
1067:As a
1040:H)(CO
997:H)(CO
978:H)(CO
886:amber
805:anion
590:= 4.2
561:Ether
360:InChI
247:E363
142:ChEBI
120:JSmol
5215:cis-
5156:NAD
5059:FADH
4836:PMID
4828:ISSN
4793:PMID
4775:ISSN
4733:PMID
4715:ISSN
4676:PMID
4658:ISSN
4619:PMID
4573:PMID
4555:ISSN
4509:PMID
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