2149PathwayAspartate Metabolism Aspartate (also named as L-aspartic acid) is an α-amino acid that can be used for protein biosynthesis. Oxalacetic acid is produced from aspartic acid by mitochondrial aspartate aminotransferase, then oxalacetic acid is reduced to malic acid by malate dehydrogenase. Malic acid enters mitochondria through mitochondrial dicarboxylate transporter and forms oxalacetic acid by facilitation of malate dehydrogenase. In the final step, oxalacetic acid is catalyzed by mitochondrial aspartate aminotransferase to form aspartate.MetabolicPW002375CenterPathwayVisualizationContext266119492453#000099PathwayVisualization21322149Aspartate Metabolism Aspartate (also named as L-aspartic acid) is an α-amino acid that can be used for protein biosynthesis. Oxalacetic acid is produced from aspartic acid by mitochondrial aspartate aminotransferase, then oxalacetic acid is reduced to malic acid by malate dehydrogenase. Malic acid enters mitochondria through mitochondrial dicarboxylate transporter and forms oxalacetic acid by facilitation of malate dehydrogenase. In the final step, oxalacetic acid is catalyzed by mitochondrial aspartate aminotransferase to form aspartate.Metabolic18495514622413Cavero S, Vozza A, del Arco A, Palmieri L, Villa A, Blanco E, Runswick MJ, Walker JE, Cerdan S, Palmieri F, Satrustegui J: Identification and metabolic role of the mitochondrial aspartate-glutamate transporter in Saccharomyces cerevisiae. Mol Microbiol. 2003 Nov;50(4):1257-69.2149Pathway495614671011Pastore D, Di Pede S, Passarella S: Isolated durum wheat and potato cell mitochondria oxidize externally added NADH mostly via the malate/oxaloacetate shuttle with a rate that depends on the carrier-mediated transport. Plant Physiol. 2003 Dec;133(4):2029-39. doi: 10.1104/pp.103.028548. Epub 2003 Dec 11.2149Pathway495715358789Hung GC, Brown CR, Wolfe AB, Liu J, Chiang HL: Degradation of the gluconeogenic enzymes fructose-1,6-bisphosphatase and malate dehydrogenase is mediated by distinct proteolytic pathways and signaling events. J Biol Chem. 2004 Nov 19;279(47):49138-50. doi: 10.1074/jbc.M404544200. Epub 2004 Sep 8.2149Pathway49581447211Steffan JS, McAlister-Henn L: Isolation and characterization of the yeast gene encoding the MDH3 isozyme of malate dehydrogenase. J Biol Chem. 1992 Dec 5;267(34):24708-15.2149Pathway1CellCL:00000006MyocyteCL:00001875HepatocyteCL:00001823NeuronCL:00005401Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote18Saccharomyces cerevisiae4932EukaryoteYeast4Arabidopsis thaliana3702EukaryoteThale cress49Bathymodiolus platifrons220390EukaryoteDeep sea mussel23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse17Rattus norvegicus10116EukaryoteRat5Bos taurus9913EukaryoteCattle10Drosophila melanogaster7227EukaryoteFruit fly6Caenorhabditis elegans6239EukaryoteRoundworm24Solanum lycopersicum4081EukaryoteTomato21Xenopus laevis8355EukaryoteAfrican clawed frog60Nitzschia sp.0001EukaryoteNitzschia42Bacteria2ProkaryoteBacteria25Escherichia coli (strain K12)83333Prokaryote19Schizosaccharomyces pombe4896Eukaryote29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast7Chlamydomonas reinhardtii3055Eukaryote5CytoplasmGO:00057376LysosomeGO:00057642MitochondrionGO:00057393Mitochondrial MatrixGO:000575924Mitochondrial Intermembrane SpaceGO:00057581CytosolGO:000582931Periplasmic SpaceGO:000562035ChloroplastGO:000950740PeriplasmGO:004259713Endoplasmic ReticulumGO:00057834PeroxisomeGO:000577710Cell MembraneGO:000588611Extracellular SpaceGO:00056157Endoplasmic Reticulum MembraneGO:000578912Mitochondrial Inner MembraneGO:000574314Mitochondrial Outer MembraneGO:000574136MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032532Inner MembraneGO:007025816Lysosomal LumenGO:004320225Golgi apparatusGO:000579415NucleusGO:00056341LiverBTO:00007597299MuscleBTO:00008871411824BrainBTO:0000142891628StomachBTO:0001307155268Blood VesselBTO:000110274118511PW_BS0000089611PW_BS0000093211PW_BS0000034311PW_BS000004422411PW_BS0000422111PW_BS000002107313PW_BS00010710813PW_BS000108188118PW_BS0000241601181PW_BS0001602253541PW_BS0000241985181PW_BS0000242905491PW_BS0000242916491PW_BS0000243183123PW_BS000024315123PW_BS0000241115121PW_BS0001111321121PW_BS0001321136121PW_BS0001131333121PW_BS00013334524121PW_BS0000281122121PW_BS0001121355171PW_BS000135232403PW_BS000024117131PW_BS000117122551PW_BS000122124151PW_BS000124406351PW_BS0001154182451PW_BS0001151181171PW_BS0001181203171PW_BS00012045424171PW_BS0001152975101PW_BS0000244793101PW_BS00011548924101PW_BS000115205561PW_BS000024501361PW_BS0001155062461PW_BS000115388161PW_BS000112181311PW_BS000018311511PW_BS0000315411PW_BS000005509516PW_BS000050261115PW_BS000026541315PW_BS000054103331PW_BS0001031471241PW_BS0001471553241PW_BS0001551572241PW_BS0001571613181PW_BS0001611783211PW_BS00017885241011PW_BS000085222341PW_BS000024224241PW_BS000024151141PW_BS00015122014PW_BS0000242892491PW_BS000024253541PW_BS00002412915121PW_BS00012934695126PW_BS00002832711125PW_BS00002834713125PW_BS0000283344121PW_BS0000283683601PW_BS000028943PW_BS000094407251PW_BS0001154141551PW_BS000115408451PW_BS0001154239556PW_BS0001154241155PW_BS0001154251355PW_BS0001151192171PW_BS00011945015171PW_BS0001153744171PW_BS00005345895176PW_BS00011545911175PW_BS00011546013175PW_BS0001152991101PW_BS0000244812101PW_BS0001154824101PW_BS000115206261PW_BS000024502461PW_BS0001152924491PW_BS0000243221231PW_BS000024126651PW_BS0001264436171PW_BS0001153016101PW_BS000024207661PW_BS00002411PW_BS00000114101PW_BS000014105113PW_BS0001051873118PW_BS00002472513PW_BS000072711113PW_BS0000713201123PW_BS00002415111PW_BS00001549711PW_BS000049171211PW_BS000017221411PW_BS000022101711PW_BS0000107028511PW_BS000070100521PW_BS00010015924PW_BS00015916611PW_BS00016615284PW_BS000152101531PW_BS0001011632181PW_BS000163219314PW_BS0000242137181PW_BS00002421013181PW_BS00002421217181PW_BS00002417018PW_BS000170226441PW_BS00002416212181PW_BS0001621951318PW_BS0000242491341PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS0000242231241PW_BS0000242941141PW_BS0000243081011PW_BS0000243125231PW_BS00002429341PW_BS00002413412121PW_BS0001343317121PW_BS0000281141112PW_BS00011413013121PW_BS000130310312PW_BS00002430412PW_BS000024383751PW_BS000100390761PW_BS0001123987171PW_BS0001133361121PW_BS000028109323PW_BS000109409115PW_BS0001153841251PW_BS0001001251351PW_BS0001251371117PW_BS00013712112171PW_BS00012113613171PW_BS0001364831110PW_BS0001154957101PW_BS00011548012101PW_BS00011530013101PW_BS000024208116PW_BS0000243911261PW_BS0001123951361PW_BS00011329111PW_BS0000292811611PW_BS0000286131PW_BS000006951721PW_BS0000951231751PW_BS00012314117191PW_BS0001412164181PW_BS00002429817101PW_BS00002433217121PW_BS000028429151PW_BS00011544717171PW_BS0001154641171PW_BS000115432511PW_BS00004335625121PW_BS0000284192551PW_BS00011545525171PW_BS00011549025101PW_BS0001155072561PW_BS000115239329PW_BS0000241893218PW_BS0000242111018PW_BS00002421425181PW_BS0000242156181PW_BS0000241901118PW_BS0000242171518PW_BS00002421815181PW_BS000024254518PW_BS0000242771218PW_BS000024644171PW_BS000508646271PW_BS000508693741PW_BS0005127081291PW_BS0005122401229PW_BS000024241529PW_BS000024123L-Aspartic acidHMDB0000191Aspartic acid (Asp, D), also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong (Wikipedia). Aspartic acid is a nonessential amino acid that is made from glutamic acid by enzymes using vitamin B6. The amino acid has important roles in the urea cycle and DNA metabolism. Aspartic acid is a major excitatory neurotransmitter, which is sometimes found to be increased in epileptic and stroke patients. It is decreased in depressed patients and in patients with brain atrophy. Aspartic acid supplements are being evaluated. Five grams can raise blood levels. Magnesium and zinc may be natural inhibitors of some of the actions of aspartic acid. Aspartic acid, with the amino acid phenylalanine, is a part of a new natural sweetener, aspartame. This sweetener is an advance in artificial sweeteners, and is probably safe in normal doses to all except phenylketonurics. The jury is still out on the long-term effects it has on many brain neurohormones. Aspartic acid may be a significant immunostimulant of the thymus and can protect against some of the damaging effects of radiation. Many claims have been made for the special value of administering aspartic acid in the form of potassium and magnesium salts. Since aspartic acid is relatively nontoxic, studies are now in progress to elucidate its pharmacological and therapeutic roles (http://www.dcnutrition.com/AminoAcids).56-84-8C000494436744517053L-ASPARTATE5745DB00128N[C@@H](CC(O)=O)C(O)=OC4H7NO4InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1CKLJMWTZIZZHCS-REOHCLBHSA-N(2S)-2-aminobutanedioic acid133.1027133.0375077170.033L-aspartic acid0-1FDB012567Asp;(+)-aspartate;(+)-aspartic acid;(2s)-aspartate;(2s)-aspartic acid;(l)-aspartate;(l)-aspartic acid;(r)-2-aminosuccinate;(s)-(+)-aspartate;(s)-(+)-aspartic acid;(s)-2-aminosuccinate;(s)-2-aminosuccinic acid;(s)-aminobutanedioate;(s)-aminobutanedioic acid;(s)-aspartate;(s)-aspartic acid;(s)-amino-butanedioate;(s)-amino-butanedioic acid;2-amino-3-methylsuccinate;2-amino-3-methylsuccinic acid;2-aminosuccinate;2-aminosuccinic acid;Aminosuccinate;Asparagate;Asparagic acid;Asparaginate;Asparaginic acid;Asparatate;Aspartate;H-asp-oh;L-(+)-aspartate;L-(+)-aspartic acid;L-aminosuccinate;L-aminosuccinic acid;L-asparagate;L-asparagic acid;L-asparaginate;L-asparaginic acid;L-aspartate;Alpha-aminosuccinate;Alpha-aminosuccinic acid;(s)-2-aminobutanedioic acid;Aspartic acid;D;L-asparaginsaeure;(s)-2-aminobutanedioatePW_C000123Asp48893911013110341104421994256631075664108685118875701608185225118021981268629012704291423633184236431577323111775101327753211378288133782893457930711280699135119878232119881117120037122120421124120809406120813418123057118123394120123398454125415297125795479125799489126955205127250501127254506127555388134Oxoglutaric acidHMDB0000208Oxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207).328-50-7C0002651309152-KETOGLUTARATE50DB02926OC(=O)CCC(=O)C(O)=OC5H6O5InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)KPGXRSRHYNQIFN-UHFFFAOYSA-N2-oxopentanedioic acid146.0981146.021523302-0.442oxoglutarate0-2FDB0033612-ketoglutarate;2-ketoglutaric acid;2-oxo-1,5-pentanedioate;2-oxo-1,5-pentanedioic acid;2-oxoglutarate;2-oxoglutaric acid;2-oxopentanedioate;2-oxopentanedioic acid;Oxoglutarate;Alpha-ketoglutaric acid;Oxoglutaric acid;A-ketoglutarate;A-ketoglutaric acid;Alpha-ketoglutarate;α-ketoglutarate;α-ketoglutaric acidPW_C000134AKG1524231414146849918673311108421263514475014552614675453751035414117543811855641326008147603615560691576092161648217865308574712227515224751915182092258374220118631981268128977054253771351337748111177523112777461297796734577970346779763277798434778425334800183688069413511316294119972406120022124120084407120174122120552414120814418120989408121146423121152424121160425122757120122831119123186450123399454123554374123718458123724459123732460125357479125400299125455481125533297125800489125929482126900501126940388126993206127066205127255506127388502148Oxalacetic acidHMDB0000223Oxaloacetic acid, also known as oxosuccinic acid or oxalacetic acid, is a four-carbon dicarboxylic acid appearing as an intermediate of the citric acid cycle. In vivo, oxaloacetate (the ionized form of oxaloacetic acid) is formed by the oxidation of L-malate, catalyzed by malate dehydrogenase, and reacts with Acetyl-CoA to form citrate, catalyzed by citrate synthase.(wikipedia) A class of ketodicarboxylic acids derived from oxalic acid. Oxaloacetic acid is an intermediate in the citric acid cycle and is converted to aspartic acidD by a transamination reaction.328-42-7C0003697030744OXALACETIC_ACID945OC(=O)CC(=O)C(O)=OC4H4O5InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)KHPXUQMNIQBQEV-UHFFFAOYSA-N2-oxobutanedioic acid132.0716132.005873238-0.362oxalacetate0-2FDB0014792-ketosuccinate;2-ketosuccinic acid;2-oxobutanedioate;2-oxobutanedioic acid;2-oxosuccinate;2-oxosuccinic acid;Ketosuccinate;Ketosuccinic acid;Oaa;Oxalacetate;Oxaloacetate;Oxaloacetic acid;Oxaloethanoate;Oxaloethanoic acid;Oxosuccinate;Oxosuccinic acid;A-ketosuccinate;A-ketosuccinic acid;Alpha-ketosuccinate;Alpha-ketosuccinic acid;3-carboxy-3-oxopropanoic acid;Keto-succinic acid;Oxalacetic acid;Oxobutanedioic acid;3-carboxy-3-oxopropanoate;Keto-succinate;OxobutanedioatePW_C000148Oaa2549691115109931109421113216888537110354481205574133603315560881616478178746822275132247517151837222083782251174411711891160127072911271729243792322775081327753311377538334779581127800911178290345800153688070013511996440612004840812006212612018012212041912412081541812120740712279937412281344312305511812340045412377711912535447912542648212543930112553729712580148912580729912689750112696550212697720712707020512725650612726138895L-Glutamic acidHMDB0000148Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid).56-86-0C000253303216015GLT30572DB00142N[C@@H](CCC(O)=O)C(O)=OC5H9NO4InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1WHUUTDBJXJRKMK-VKHMYHEASA-N(2S)-2-aminopentanedioic acid147.1293147.053157781-0.263L-glutamic acid0-1FDB012535(2s)-2-aminopentanedioate;(2s)-2-aminopentanedioic acid;(s)-(+)-glutamate;(s)-(+)-glutamic acid;(s)-2-aminopentanedioate;(s)-2-aminopentanedioic acid;(s)-glutamate;(s)-glutamic acid;1-amino-propane-1,3-dicarboxylate;1-amino-propane-1,3-dicarboxylic acid;1-aminopropane-1,3-dicarboxylate;1-aminopropane-1,3-dicarboxylic acid;2-aminoglutarate;2-aminoglutaric acid;2-aminopentanedioate;2-aminopentanedioic acid;Aciglut;Aminoglutarate;Aminoglutaric acid;E;Glt;Glu;Glusate;Glut;Glutacid;Glutamicol;Glutamidex;Glutaminate;Glutaminic acid;Glutaminol;Glutaton;L-(+)-glutamate;L-(+)-glutamic acid;L-glu;L-glutamate;L-glutaminate;L-glutaminic acid;L-a-aminoglutarate;L-a-aminoglutaric acid;L-alpha-aminoglutarate;L-alpha-aminoglutaric acid;A-aminoglutarate;A-aminoglutaric acid;A-glutamate;A-glutamic acid;Alpha-aminoglutarate;Alpha-aminoglutaric acid;Alpha-glutamate;Alpha-glutamic acid;Acide glutamique;Acido glutamico;Acidum glutamicum;Glutamate;Glutamic acid;L-glutaminsaeurePW_C000095Glu1624436581191138416414969911054214485014562614625453231115344113541511754391185565132563110756321085859105600614760711576191946531856838187684418870927270937171652057182207751422475181518208225837322011792198118551611200422212621311268328912697290423483154234931842845320770202537733213377525112779713467797732777981347782913458064913512002312412004012212008640712034740612069212612081641812114742312115342412115742512283311912299712012329944312340145412371945812372545912372946012540129912541829712545748112566747912576930112580248912694138812699520612716250112725750640034Hydrogen IonHMDB0059597Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])C000801038153781010[H+]HInChI=1S/p+1GPRLSGONYQIRFK-UHFFFAOYSA-Nhydron1.00791.0078250320hydron10H+;H(+);Hydrogen cation;Hydron;ProtonPW_C040034H+2154670875315788318483111621463261464542231492780174250224254424547104576184694705241103532711153531125626108563910756991005720105574211759631476037155607015760931616130159623216664831786601152669210168431886910187710016371682057191206745321974542207472222752521375322107558212757216075901708195225821815182432268413162842022491391959155249119151641201528112181285122462861226628712521227132572231332529415330308423293154235431842401322424053124245432076912293771361337721013477372331778041147795513277990327779913477837934579929130800193688038731080388304807221199382312494823383110550388112855941132803901155373981155391181158563361162051091199734061201934071205491221205934091211704241211714251225694181226153841226871251227581201231831351232181371237424591237434601251414541251881211252731361253594791255504811257304831257362971258092991265174951267174891267664801268233001269025011272132081283085061283613911284303951144NADHHMDB0001487NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).58-68-4C0000443915316908NADH388299DB00157NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O14P2InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BOPGDPNILDQYTO-NNYOXOHSSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid665.441665.124771695-2.358NADH0-2FDB0226491,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotidePW_C001144NADH14341533490864810111521275514695422304927811728362931099480618481218482128490464959315169955240103533211153581125466123547912555931355698100573710858291415915147594515160271556079161638716472178677111768931607011188709916371722057195206746222282442268360225908622411809198118212161232024913003298130153001325522342403322426183157710713277123133772081347737133177651336776683347770033277707130779171137798634780009368806911199382212411054938811285494115838118119955406120172407120378122120986408121162425121244126121693429121818383122616384122745120123127447123138136123551374123734460123814443124242464124371398125189121125345479125531481125762297125808299125926482126516495126767480126888501127385502128090390128362391128429395101L-Malic acidHMDB0000156Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. Apples contain malic acid, which contributes to the sourness of a green apple. Malic acid can make a wine taste tart, although the amount decreases with increasing fruit ripeness. (wikipedia). In its ionized form malic acid is called malate. Malate is an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. In humans, malic acid is both derived from food sources and synthesized in the body through the citric acid cycle or Krebs cycle which takes place in the mitochondria. Malate's importance to the production of energy in the body during both aerobic and anaerobic conditions is well established. Under aerobic conditions, the oxidation of malate to oxaloacetate provides reducing equivalents to the mitochondria through the malate-aspartate redox shuttle. During anaerobic conditions, where a buildup of excess of reducing equivalents inhibits glycolysis, malic acid's simultaneous reduction to succinate and oxidation to oxaloacetate is capable of removing the accumulating reducing equivalents. This allows malic acid to reverse hypoxia's inhibition of glycolysis and energy production. In studies on rats it has been found that only tissue malate is depleted following exhaustive physical activity. Other key metabolites from the citric acid cycle needed for energy production were found to be unchanged. Because of this, a deficiency of malic acid has been hypothesized to be a major cause of physical exhaustion. Notably, the administration of malic acid to rats has been shown to elevate mitochondrial malate and increase mitochondrial respiration and energy production.97-67-6C0014922265630797193317O[C@@H](CC(O)=O)C(O)=OC4H6O5InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1BJEPYKJPYRNKOW-REOHCLBHSA-N(2S)-2-hydroxybutanedioic acid134.0874134.0215233020.213(-)-malic acid0-2FDB001044(-)-(s)-malate;(-)-(s)-malic acid;(-)-hydroxysuccinate;(-)-hydroxysuccinic acid;(-)-l-malic acid;(-)-malic acid;(2s)-2-hydroxybutanedioate;(2s)-2-hydroxybutanedioic acid;(s)-(-)-hydroxysuccinate;(s)-(-)-hydroxysuccinic acid;(s)-hydroxybutanedioate;(s)-hydroxybutanedioic acid;(s)-malic acid;(s)-hydroxy-butanedioate;(s)-hydroxy-butanedioic acid;Apple acid;L-(-)-malic acid;L-apple acid;L-hydroxybutanedioate;L-hydroxybutanedioic acid;L-hydroxysuccinate;L-hydroxysuccinic acid;Malic acid;S-(-)-malate;S-(-)-malic acid;S-2-hydroxybutanedioate;S-2-hydroxybutanedioic acid;L-2-hydroxybutanedioic acid;L-malic acid;Malate;(-)-l-malate;(s)-malate;L-2-hydroxybutanedioate;L-malatePW_C000101Malate262410983172182387253871035735108604615561061616453107649117874512197452220747922242455318424563157714713378766111790511327905711280026368119988406121441122122394124122401407122771120123999135124964118124971119125368479126066297126535299126546481126910501127519205128108388128118206721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium664.433664.116946663-2.5981-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-1FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nadPW_C000721NAD1404150335386511011142113443127351466542229492779172835293107948071848131848192849026496031516795523810353341115360112546912354821255590135561011856961005738108582714159121475942151602415560721576076161638516469178677211768901607012188709716371742057197206740519874592228241226835922590852241181921612322249130062981301830013256223424043224261931577104132771201337720913477370331776503367766733477702332777091307791511377983347784063568000636880690119938251241105523881127501661128539411992912211995240612017140712083441912098440812115942512124212612125942912181738312261438412274212012313044712314113612341945512354937412373146012381244312382946412437039812518712112531929712534247912553048112580629912582549012592448212651549512676548012688550112727850712738350212808939012836039112842839510406Aspartate aminotransferase, mitochondrialQ01802
Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol (By similarity).
AAT1292.6.1.17668160766916389662399969UnknownUnknown181.3.1.716083161612116268451896885160703616370631887210210721321172172127223213723721472412157283190730119873052167392217741221892752541185427713608764413609864613698525313698622613698769313698824913707970810482Mitochondrial dicarboxylate transporterQ06143
Mitochondrial dicarboxylic transporter catalyzing the exchange of dicarboxylic acids like malate and succinate for inorganic phosphate. Required for growth on ethanol and acetate.
DIC129896724010111Malate dehydrogenase, cytoplasmicP22133
The isoenzyme MDH2 may function primarily in the glyoxylate cycle.
MDH2291.1.1.378028160896824110483Mitochondrial aspartate-glutamate transporter AGC1Q12482
Calcium-dependent mitochondrial aspartate and glutamate carrier. Transport of glutamate in mitochondria is required for mitochondrial transamination reactions and ornithine synthesis. Plays also a role in malate-aspartate NADH shuttle, which is critical for growth on acetate and fatty acids.
AGC12989692404121aspartate transaminase18PW_P004121111411040623530Malate dehydrogenase, cytoplasmic18PW_P00353010364996914213malate-α-ketoglutarate carrier18PW_P00421311260104823668Malate dehydrogenase, mitochondrial18PW_P003668105361011124214Aspartate-glutamate carrier, mitochondrial18PW_P00421411261104836257falsePW_R006257Right255961231Compoundtrue255971341Compoundfalse255981481Compoundtrue25599951Compoundfalse618641212.6.1.16265falsePW_R006265Right256291481Compoundfalse25630400341Compoundfalse2563111441Compoundfalse256321011Compoundfalse256337211Compoundfalse619435306266falsePW_R006266Left2563411441Compoundfalse25635400341Compoundfalse256361481Compoundfalse256371011Compoundfalse256387211Compoundfalse619536686186falsePW_R006186Right25319951Compoundfalse253201481Compoundtrue253211231Compoundtrue253221341Compoundfalse61374121524PW_T0005246681011Compound188161Right45142132015-12-03T14:19:37-07:002015-12-03T14:19:37-07:00162525PW_T0005256691231Compound161188Right45242142015-12-03T14:50:43-07:002015-12-03T14:50:43-07:00162773041233false55135410regular100110773051343false67645410regular100110773061483false109635410regular10011077307953false98146410regular100110773084003455false133245110regular787877309114460false134632410regular5030773101013false182135410regular1001007731172159false169132410regular5030773121011613false1821128910regular10010077313114460false1431128210regular5030773144003455false1307140210regular7878773151483false1136129010regular1001107731672159false1736128410regular503077317953false986137010regular100110773181233false551129010regular100110773191343false671137010regular10011037247104062396false8013648subunitregular160803724899692false14713678proteinregular15070372491048224076false179611398subunitregular1507037250101112416false152613018subunitregular1608037251104062396false78613008subunitregular160809492611048376false52611398subunitregular15070303674121213236588372473036835302132365893724830369421321323659037249303703668213236591372503037141212132365923725180381042142132945106949261111403M651 404 C681 404 771 404 801 404 5false18111404M726 454 C726 417 771 404 801 404 5false18111405M1096 404 C1066 404 991 404 961 404 5false18trueM 25.946855044164835 520.261556296296 L 11 519 L 17.380887721185843 532.5751343230784false111406M1031 464 C1029 421 991 404 961 404 5false18trueM 25.946855044164835 520.261556296296 L 11 519 L 17.380887721185843 532.5751343230784false111407M1196 404 C1226 404 1441 402 1471 402 5false18111408M1371 451 C1370 414 1422 402 1471 402 5false18111409M1371 354 C1371 385 1382 402 1471 402 5false18111410M1821 404 C1791 404 1651 402 1621 402 5false18trueM 409.94685504416486 520.261556296296 L 395 519 L 401.38088772118584 532.5751343230784false111411M1716 354 C1715 396 1706 403 1621 402 5false18trueM 409.94685504416486 520.261556296296 L 395 519 L 401.38088772118584 532.5751343230784false111412M1871 454 C1871 484 1871 1109 1871 1139 83false18111413M1871 1289 C1871 1241 1871 1239 1871 1209 83false18trueM 919.9468550441649 391.261556296296 L 905 390 L 911.3808877211858 403.5751343230783false111414M1456 1312 C1454 1341 1476 1340 1526 1341 5false18trueM 1081.9468550441647 943.261556296296 L 1067 942 L 1073.380887721186 955.5751343230784false111415M1346 1402 C1343 1328 1424 1341 1526 1341 5false18trueM 1081.9468550441647 943.261556296296 L 1067 942 L 1073.380887721186 955.5751343230784false111416M1236 1340 C1266 1340 1496 1341 1526 1341 5false18trueM 1081.9468550441647 943.261556296296 L 1067 942 L 1073.380887721186 955.5751343230784false111417M1821 1339 C1791 1339 1716 1341 1686 1341 5false18111418M1761 1314 C1760 1345 1715 1342 1686 1341 5false18111419M1036 1370 C1036 1339 1004 1340 946 1340 5false18111420M1136 1340 C1106 1340 976 1340 946 1340 5false18111421M651 1340 C681 1340 756 1340 786 1340 5false18trueM 229.94685504416483 609.261556296296 L 215 608 L 221.38088772118584 621.5751343230784false111422M726 1365 C725 1332 721 1341 786 1340 5false18trueM 229.94685504416483 609.261556296296 L 215 608 L 221.38088772118584 621.5751343230784false3664343M601 1290 C601 1260 601 1239 601 1209 83false183664344M601 454 C601 484 601 1109 601 1139 83false18trueM 236.94685504416483 298.261556296296 L 222 297 L 228.38088772118584 310.5751343230783false22867213262571608774077304111403Left8774177305111404Left8774277306111405Right8774377307111406Right2270261863036722868213262651608774477306111407Left8774577308111408Left8774677309111409Left8774777310111410Right8774877311111411Right2270361943036822869213262661608774977313111414Left8775077314111415Left8775177315111416Left8775277312111417Right8775377316111418Right2270461953037022870213261861608775477317111419Left8775577315111420Left8775677318111421Right8775777319111422Right2270561373037110075242132246577310111412Left246677312111413Right75430369451781635252132157139773183664343Left157140773043664344Right2477380381045214629414721.01.002904844974201M225 326 C225 276 275 226 325 226 C870 226 1580 226 2125 226 C2175 226 2225 276 2225 326 C2225 719 2225 1230 2225 1623 C2225 1673 2175 1723 2125 1723 C1580 1723 870 1723 325 1723 C275 1723 225 1673 225 1623 C225 1230 225 719 225 326 1true62000.01497.04202M125 225 C125 175 175 125 225 125 C832 125 1621 125 2228 125 C2278 125 2328 175 2328 225 C2328 679 2328 1270 2328 1724 C2328 1774 2278 1824 2228 1824 C1621 1824 832 1824 225 1824 C175 1824 125 1774 125 1724 C125 1270 125 679 125 225 1true62203.01699.04203M426 1275 C426 1225 476 1175 526 1175 C950 1175 1502 1175 1926 1175 C1976 1175 2026 1225 2026 1275 C2026 1322 2026 1384 2026 1431 C2026 1481 1976 1531 1926 1531 C1502 1531 950 1531 526 1531 C476 1531 426 1481 426 1431 C426 1384 426 1322 426 1275 84true61600.0356.04205M325 1186 C325 1136 375 1086 425 1086 C910 1086 1542 1086 2027 1086 C2077 1086 2127 1136 2127 1186 C2127 1289 2127 1422 2127 1525 C2127 1575 2077 1625 2027 1625 C1542 1625 910 1625 425 1625 C375 1625 325 1575 325 1525 C325 1422 325 1289 325 1186 84true61802.0539.0210215Mitochondria1133947201.61.6160156991239887300106021531651441853591