400PathwayAerobic Glycolysis (Warburg Effect)The Warburg Effect refers to the phenomenon that occurs in most cancer cells where instead of generating energy with a low rate of glycolysis followed by oxidizing pyruvate via the Krebs cycle in the mitochondria, the pyruvate from a high rate of glycolysis undergoes lactic acid fermentation in the cytosol. As the Krebs cycle is an aerobic process, in normal cells lactate production is reserved for anaerobic conditions. However, cancer cells preferentially utilize glucose for lactate production via this “aerobic glycolysis”, even when oxygen is plentiful. The Warburg Effect is thought to be the result of mutations to oncogenes and tumour suppressor genes. It may be an adaptation to low-oxygen environments within tumours, the result of cancer genes shutting down the mitochondria, or a mechanism to aid cell proliferation via increased glycolysis. Proliferation may occur due to the accumulation of glycolytic intermediates (which lead to the production of nucleotides, amino acids, and fatty acids) after the final enzymatic reaction of glycolysis (phosphoenolpyruvate into pyruvate) is slowed down. This reaction produces lactic acid which leads to a low pH microenvironment and the lactate shuttle can activate angiogenesis factors from surrounding cells. The Warburg Effect involves numerous pathways, including growth factor stimulation, transcriptional activation, and glycolysis promotion.MetabolicPW000630TopLeftPathwayVisualizationContext83070006000#000099PathwayVisualization378400Aerobic Glycolysis (Warburg Effect)The Warburg Effect refers to the phenomenon that occurs in most cancer cells where instead of generating energy with a low rate of glycolysis followed by oxidizing pyruvate via the Krebs cycle in the mitochondria, the pyruvate from a high rate of glycolysis undergoes lactic acid fermentation in the cytosol. As the Krebs cycle is an aerobic process, in normal cells lactate production is reserved for anaerobic conditions. However, cancer cells preferentially utilize glucose for lactate production via this “aerobic glycolysis”, even when oxygen is plentiful. The Warburg Effect is thought to be the result of mutations to oncogenes and tumour suppressor genes. It may be an adaptation to low-oxygen environments within tumours, the result of cancer genes shutting down the mitochondria, or a mechanism to aid cell proliferation via increased glycolysis. Proliferation may occur due to the accumulation of glycolytic intermediates (which lead to the production of nucleotides, amino acids, and fatty acids) after the final enzymatic reaction of glycolysis (phosphoenolpyruvate into pyruvate) is slowed down. This reaction produces lactic acid which leads to a low pH microenvironment and the lactate shuttle can activate angiogenesis factors from surrounding cells. The Warburg Effect involves numerous pathways, including growth factor stimulation, transcriptional activation, and glycolysis promotion.Metabolic1886Tyrosine kinase regulationInhibitorySubPathway14301134ProteinComplex21431471ProteinComplex2196619995572Gogvadze V, Zhivotovsky B, Orrenius S: The Warburg effect and mitochondrial stability in cancer cells. Mol Aspects Med. 2010 Feb;31(1):60-74. doi: 10.1016/j.mam.2009.12.004. Epub 2009 Dec 6.400Pathway196719258498Samudio I, Fiegl M, Andreeff M: Mitochondrial uncoupling and the Warburg effect: molecular basis for the reprogramming of cancer cell metabolism. Cancer Res. 2009 Mar 15;69(6):2163-6. doi: 10.1158/0008-5472.CAN-08-3722. Epub 2009 Mar 3.400Pathway196819460998Vander Heiden MG, Cantley LC, Thompson CB: Understanding the Warburg effect: the metabolic requirements of cell proliferation. Science. 2009 May 22;324(5930):1029-33. doi: 10.1126/science.1160809.400Pathway197713298683WARBURG O: On the origin of cancer cells. Science. 1956 Feb 24;123(3191):309-14.400Pathway33775530255018Fitzgerald G, Soro-Arnaiz I, De Bock K: The Warburg Effect in Endothelial Cells and its Potential as an Anti-angiogenic Target in Cancer. Front Cell Dev Biol. 2018 Sep 11;6:100. doi: 10.3389/fcell.2018.00100. eCollection 2018.400Pathway33775730487597Papa S, Choy PM, Bubici C: The ERK and JNK pathways in the regulation of metabolic reprogramming. Oncogene. 2019 Mar;38(13):2223-2240. doi: 10.1038/s41388-018-0582-8. Epub 2018 Nov 28.400Pathway33775823216817Polet F, Feron O: Endothelial cell metabolism and tumour angiogenesis: glucose and glutamine as essential fuels and lactate as the driving force. J Intern Med. 2013 Feb;273(2):156-65. doi: 10.1111/joim.12016.400Pathway6MyocyteCL:00001875HepatocyteCL:00001821CellCL:00000007Epithelial CellCL:00000668Beta cellCL:000063910Glial cellCL:00001252Platelet CL:00002333NeuronCL:00005404CardiomyocyteCL:000074612AstrocyteCL:000012728MacrophageCL:000023523T CellCL:00000841Homo sapiens9606EukaryoteHuman24Solanum lycopersicum4081EukaryoteTomato4Arabidopsis thaliana3702EukaryoteThale cress3Escherichia coli562Prokaryote18Saccharomyces cerevisiae4932EukaryoteYeast12Mus musculus10090EukaryoteMouse23Pseudomonas aeruginosa287Prokaryote5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly6Caenorhabditis elegans6239EukaryoteRoundworm2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel60Nitzschia sp.0001EukaryoteNitzschia451Picea sitchensis3332EukaryoteSitka spruce29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast202Spathaspora passalidarum340170EukaryoteSpathaspora passalidarum196Homo1924EukaryoteHuman240Plasmodium falciparums121Eukaryote135Felinus9685EukaryoteCat5CytoplasmGO:00057371CytosolGO:000582925Golgi ApparatusGO:00057946LysosomeGO:00057643Mitochondrial MatrixGO:000575911Extracellular SpaceGO:00056152MitochondrionGO:000573931Periplasmic SpaceGO:000562014Mitochondrial Outer MembraneGO:000574115NucleusGO:00056344PeroxisomeGO:000577713Endoplasmic ReticulumGO:00057837Endoplasmic Reticulum MembraneGO:000578910Cell MembraneGO:000588627Peroxisome MembraneGO:000577835ChloroplastGO:000950712Mitochondrial Inner MembraneGO:000574332Inner MembraneGO:007025834Plant-Type VacuoleGO:000032519Sarcoplasmic ReticulumGO:001652926Golgi Apparatus MembraneGO:000013924Mitochondrial Intermembrane SpaceGO:000575816Lysosomal LumenGO:004320218Melanosome MembraneGO:003316220Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520236MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016840PeriplasmGO:00425978Smooth Endoplasmic Reticulum GO:000579039Mitochondrial membraneGO:00319669MuscleBTO:0000887141181LiverBTO:00007597298Blood VesselBTO:0001102741125IntestineBTO:000064818PancreasBTO:00009887Nervous SystemBTO:00014842Endothelium BTO:00003935cardiocyteBTO:00015394Adrenal MedullaBTO:000004971828StomachBTO:00013071552611HeartBTO:000056273106KidneyBTO:000067171824BrainBTO:000014289163Sympathetic Nervous 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is a monosaccharide containing six carbon atoms and an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In water solution both forms are in equilibrium and at pH 7 the cyclic one is the predominant. Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. In animals glucose arises from the breakdown of glycogen in a process known as glycogenolysis. Glucose is synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis.2280-44-6C0003157934167GLC5589[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])OC6H12O6InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1WQZGKKKJIJFFOK-GASJEMHNSA-N(3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol180.1559180.0633881160.645glucose00FDB012530Roferose st;(+)-glucose;Anhydrous dextrose;Cpc hydrate;Cerelose;Cerelose 2001;Clearsweet 95;Clintose l;Corn sugar;D(+)-glucose;Dextropur;Dextrose;Dextrosol;Glucodin;Glucolin;Glucose;Goldsugar;Grape sugar;Meritose;Staleydex 111;Staleydex 95m;Tabfine 097(hs);Vadex;D-glc;D-glcp;D-glucosePW_C000077D-Glc1452501460261461511506215404321939243942679602721152723613027663114293593356926589614859221495923152595415363671076368108686919269041937085200724421511765114117661324244031842441315770853267711732777923336779893467823635278248353782623567888111379056112121166424121167416121169423121251429121361124121373419122098126122385436122388437122399407122676409123738459123739452123741458123821464123920118123932455124649443124939471124959472124969119125251137125937488125967492126034299126046490126254301126540481126809483127397505127423509127486388127498507127817207128113206128408208414Adenosine triphosphateHMDB0000538Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).56-65-5C00002595715422ATP5742DB00171NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H16N5O13P3InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1ZKHQWZAMYRWXGA-KQYNXXCUSA-N({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid507.181506.995745159-2.057adenosine triphosphate0-3FDB0218135'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acidPW_C000414ATP922146082661641422478137333279959343997632105182112102146492156142160582405592434272726462812293029663163723616613617514399234474314768914864545032895035265155752059752151005250104529110153131115346112539010354061175430118544312055421295556132556913356031355621108584614358541465876107589714759241516048155610916162301666493178683918868701606976199715720571842067209210722521372292117298198730221673902177408218743216374812227499190818622511847277119031701201028112039164121782851257822612691290132642231532730842326315426213224269431877028253772181347723332977468333776323367803733278041350781681287821435178240353784113357849411578850130788653317891933480028368800461848067411985629194826124113234941132823881162801091199141221199924061201544071202453821203624121212464291213921231213974331214714081219744101220651251220793831220834051224024221224444351229193991230094461238164641239514471239564681240293741245274441246161361246303981246343761249434721249723751250114701253042971253714791253922991255154811255954841261234851262203001262344951262404781265474911265964991269135011271233891277315161277813951277963901278012091281195081281675171407708911083Glucose 6-phosphateHMDB0001401Glucose 6 phosphate (alpha-D-glucose 6 phosphate or G6P) is the alpha-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Glucose 6 phosphate is an ester of glucose with phosphoric acid, made in the course of glucose metabolism by mammalian and other cells. It is a normal constituent of resting muscle and probably is in constant equilibrium with fructose-6-phosphate. (Stedman, 26th ed). Glucose-6-phosphate is a phosphorylated glucose molecule on carbon 6. When glucose enters a cell, it is immediately phosphorylated to G6P. This is catalyzed with hexokinase enzymes, thus consuming one ATP. A major reason for immediate phosphorylation of the glucose is so that it cannot diffuse out of the cell. The phosphorylation adds a charged group so the G6P cannot easily cross cell membranes. G6P can travel down two metabolic pathways, glycolysis and the pentose phosphate pathway. In addition to the metabolic pathways, G6P can also be stored as glycogen in the liver if blood glucose levels are high. If the body needs energy or carbon skeletons for syntheses, G6P can be isomerized to Fructose-6-phosphate and then phosphorylated to Fructose-1,6-bisphosphate. Note, the molecule now has 2 phosphoryl groups attached. The addition of the 2nd phosphoryl group is an irreversible step, so once this happens G6P will enter glycolysis and be turned into pyruvate (ATP production occurs). If blood glucose levels are high, the body needs a way to store the excess glucose. After being converted to G6P, phosphoglucose mutase (isomerase) can turn the molecule into glucose-1-phosphate. Glucose-1-phosphate can then be combined with uridine triphosphate (UTP) to form UDP-glucose. This reaction is driven by the hydrolysis of pyrophosphate that is released in the reaction. Now, the activated UDP-glucose can add to a growing glycogen molecule with the help of glycogen synthase. This is a very efficient storage mechanism for glucose since it costs the body only 1 ATP to store the 1 glucose molecule and virtually no energy to remove it from storage. It is important to note that glucose-6-phosphate is an allosteric activator of glycogen synthase, which makes sense because when the level of glucose is high the body should store the excess glucose as glycogen. On the other hand, glycogen synthase is inhibited when it is phosphorylated by protein kinase a during times of high stress or low blood glucose levels. -- Wikipedia.56-73-5C0009259584170GLC-6-P5743OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1OC6H13O9PInChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1NBSCHQHZLSJFNQ-GASJEMHNSA-N{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid260.1358260.029718526-0.926glucose 6-phosphate0-2FDB021818D(+)-glucopyranose 6-phosphate;D-glucose 6-phosphate;D-glucose-6-dihydrogen phosphate;D-hexose 6-phosphate;Glucose 6-phosphate;Glucose-6-phosphate;Robison ester;A-d-glucose 6- phosphate;Alpha-d-glucose 6- phosphate;Alpha-d-glucose 6-phosphate;Alpha-d-hexose 6-phosphate;6-o-phosphono-d-glucopyranose;Glc6p;D-glucopyranose 6-phosphoric acid;D-glucose 6-phosphoric acidPW_C001083Gluc-6P1118818042238118312529589814759251516065158687116074031981191216412577225770861327793633677949130781641111208241221211721241212001251212644291234091351237441181237701361238344641258152971259382991272672051273983881034Adenosine diphosphateHMDB0001341Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.58-64-0C00008602216761ADP5800NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1XTWYTFMLZFPYCI-KQYNXXCUSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid427.2011427.029414749-2.126adenosine-diphosphate0-2FDB021817Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acidPW_C001034ADP23413484152248213801596315978310611415182190149210418211310216158240859243527272847273646285529316572363561440023447631477091503626515775208975217100531511153491125392103544612055441295572133562410857411175764101584914358561465878107589914759261516050155611116162311666495178670094684118868721607159205718720672082107226213723121173001987303216739121774102187433163748322281872251185127711905170120132811218028513262223153293084232831542398313426223224269631877029253770871327721613477306329774723337766333678039332780433507817012878215351782443537841433578495115787053317884913078920334800303688062211880651135806761199482712411328338811620410911994412211999440612015640712031838212036641212124842912139412312139943312147240812189938312197641012206412512208540512240542212244543512297339912301344612381846412395344712395846812403037412445239812452944412461513612463637612494747212497537512501247012533429712537347912549229912551748112564548412612548512621930012623549512624247812655049112659749912691550112773351612778039512779739012780320912812250812816851712831338979Fructose 6-phosphateHMDB0000124Fructose 6-phosphate is an important intermediate in the Carbohydrates pathway. The interconversion of glucose-6-phosphate and fructose-6-phosphate, the second step of the Embden-Meyerhof glycolytic pathway, is catalyzed by the enzyme phosphoglucose isomerase (PGI). In gluconeogenesis, fructose-6-phosphate is the immediate precursor of glucose-6-phosphate (wikipedia).643-13-0C000856950715946FRUCTOSE-6P62713OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=OC6H13O9PInChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1GSXOAOHZAIYLCY-HSUXUTPPSA-N{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid260.1358260.029718526-1.056D-fructose 6-phosphate0-2FDB021896D-fructose 6-phosphate;D-fructose 6-phosphorate;D-fructose 6-phosphoric acid;D-fructose-6-p;D-fructose-6-phosphate;Fpc;Fru-6-p;Fructose 6-phosphate;Fructose-6-p;Fructose-6-phosphate;Fructose-6p;Neuberg esterPW_C000079Fru6P38881014317852590414759321516465108687816012987166132972254267631577093132772941117791911280660135120142122120716407121178124123321119123750118125504297125944299127041205127404388833Fructose 1,6-bisphosphateHMDB0001058Fructose 1,6-bisphosphate is fructose sugar or fructosephosphate that has been phosphorylated on carbons 1 and 6. The beta-D-form of this compound is very common in cells. The vast majority of glucose and fructose entering a cell is converted to fructose 1,6-bisphosphate at some point. Fructose 1,6-bisphosphate is a key component in the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate The enzyme phosphofructokinase uses ATP to transfer a phosphate group to fructose 6-phosphate to form fructose 1, 6-bisphosphate. fructose The enzyme aldolase splits fructose 1, 6-bisphosphate into two sugars that are isomers of each other. These two sugars are dihydroxyacetone phosphate and glyceraldehyde phosphate. Fructose 1,6-bisphosphate is an allosteric activator of pyruvate kinase.488-69-7C0035444555716905FRUCTOSE-16-DIPHOSPHATE393165O[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=OC6H14O12P2InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1RNBGYGVWRKECFJ-ARQDHWQXSA-N{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid340.1157339.996048936-1.337[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid0-4FDB022397D-fructose 1,6-biphosphate;D-fructose 1,6-bis(dihydrogen phosphate);D-fructose 1,6-bisphosphate;D-fructose 1,6-diphosphate;D-fructose-1,6-bisphosphate;D-fructose-1,6-diphosphate;Diphosphofructose;Esafosfan;Esafosfina;Fdp;Fosfructose;Fructose 1,6-bis;Fructose 1,6-bisphosphate;Fructose 1,6-diphosphate;Harden-young ester;1,6-di-o-phosphono-alpha-d-fructofuranose;Alpha fructose 1,6-diphosphate;1,6-di-o-phosphono-a-d-fructofuranose;1,6-di-o-phosphono-α-d-fructofuranosePW_C000833Fru1,6P1021817902590514759331516880160133582257709513277931111120727122121180124123328135123752118125946299127406388423MagnesiumHMDB0000547Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.22537-22-0C003058881842013-HYDROXY-MAGNESIUM-PROTOPORP865DB01378[Mg++]MgInChI=1S/Mg/q+2JLVVSXFLKOJNIY-UHFFFAOYSA-Nmagnesium(2+) ion24.30523.9850418980magnesium(2+) ion22FDB003518Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+PW_C000423Mg2+868227426816476272726811581918883229363998339922111674614834915294317641421241024115929422331262933737454031477491486954497456525310453291115356112537610359061475934151603815560941616250166648417865941646881160697919971702057194206722721372332117250214731021673131987473222117631321184321012312225123242491251328812581226127292901527528515337308771371337723632977937336783933347841733578489115785223317853635678574130800203688004518480048372806231188065413580865158096525381841519383238394900271085962231105593901156873981199744061200701221202473821207024071209814081211811241212654291213194191219241251220864051224084221227591201229213991233071191235463741238354641238894551244771361246373761249783751254472971255984841256694791257774811259214821259472991259734951260004901262434781265534911267533001271253891271645011273805021274073881274515071278042091281255081283473951407738911134Dihydroxyacetone phosphateHMDB0001473Dihydroxyacetone phosphate, also known as 3-phosphate, dihydroxyacetone or 3-hydroxy-2-oxopropyl phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Dihydroxyacetone phosphate has been detected in multiple biofluids, such as saliva and blood. Within the cell, dihydroxyacetone phosphate is primarily located in the peroxisome, mitochondria and cytoplasm. Dihydroxyacetone phosphate exists in all living organisms, ranging from bacteria to humans. In humans, dihydroxyacetone phosphate is involved in cardiolipin biosynthesis CL(i-13:0/i-21:0/a-17:0/i-14:0) pathway, cardiolipin biosynthesis CL(i-14:0/a-13:0/i-19:0/a-25:0) pathway, cardiolipin biosynthesis CL(i-12:0/i-13:0/i-17:0/i-12:0) pathway, and cardiolipin biosynthesis CL(a-13:0/18:2(9Z,11Z)/i-20:0/i-22:0) pathway. Dihydroxyacetone phosphate is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(8:0/a-21:0/13:0) pathway, de novo triacylglycerol biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(i-20:0/i-21:0/19:0) pathway, and de novo triacylglycerol biosynthesis TG(i-22:0/17:0/i-14:0) pathway. Outside of the human body, dihydroxyacetone phosphate can be found in a number of food items such as towel gourd, boysenberry, jujube, and prunus (cherry, plum). This makes dihydroxyacetone phosphate a potential biomarker for the consumption of these food products. Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.57-04-5C0011166816108DIHYDROXY-ACETONE-PHOSPHATE648DB04326OCC(=O)COP(O)(O)=OC3H7O6PInChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)GNGACRATGGDKBX-UHFFFAOYSA-N(3-hydroxy-2-oxopropoxy)phosphonic acid170.0578169.998024468-0.893dihydroxyacetone-phosphate0-2FDB0016181,3-dihydroxy-2-propanone mono(dihydrogen phosphate);1,3-dihydroxy-2-propanone phosphate;1,3-dihydroxyacetone 1-phosphate;1-hydroxy-3-(phosphonooxy)-2-propanone;1-hydroxy-3-(phosphonooxy)acetone;Dhap;Di-oh-acetone-p;Dihydroxy-acetone-p;Dihydroxy-acetone-phosphate;Dihydroxyacetone 3-phosphate;Dihydroxyacetone monophosphate;Dihydroxyacetone phosphate;Dihydroxyacetone-p;Dihydroxyacetone-phosphate;Glycerone phosphate;Glycerone-phosphate;Phosphoric acid ester with 1,3-dihydroxy-2-propanone;1,3-dihydroxy-2-propanone monodihydrogen phosphate;3-hydroxy-2-oxopropyl phosphate;Glycerone monophosphate;1,3-dihydroxy-2-propanone monodihydrogen phosphoric acid;Glycerone phosphoric acid;1,3-dihydroxy-2-propanone phosphoric acid;1,3-dihydroxyacetone 1-phosphoric acid;3-hydroxy-2-oxopropyl phosphoric acid;Dihydroxyacetone monophosphoric acid;Dihydroxyacetone phosphoric acid;Glycerone monophosphoric acidPW_C001134Dhapp1026814742330554253425813108590814759361516884160426603157709813277934111783743457855933493824124110551388115839118120733122122564418122590408123333135125137454125162374125787297125950299126712489126736482127242205128303506128330502869D-Glyceraldehyde 3-phosphateHMDB0001112Glyceraldehyde 3-phosphate (G3P) or triose phosphate is an aldotriose, an important metabolic intermediate in both glycolysis and gluconeogenesis, and in tryptophan biosynthesis. G3P is formed from Fructose-1,6-bisphosphate, Dihydroxyacetone phosphate (DHAP),and 1,3-bisphosphoglycerate, (1,3BPG), and this is how glycerol (as DHAP) enters the glycolytic and gluconeogenesis pathways.591-59-3C0066172917138GAP709DB02263OC(COP(O)(O)=O)C=OC3H7O6PInChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)LXJXRIRHZLFYRP-UHFFFAOYSA-N(2-hydroxy-3-oxopropoxy)phosphonic acid170.0578169.998024468-0.923glyceraldehyde 3 phosphate0-2FDB0016192-hydroxy-3-(phosphonooxy)-propanal;3-phosphoglyceraldehyde;D-glyceraldehyde 3-phosphate;D-glyceraldehyde-3-p;Dl-glyceraldehyde 3-phosphate;Gap;Glyceraldehyde-3-p;Glyceraldehyde-3-phosphate;Glyceraldehyde-p;Glyceraldehyde-phosphate;2-hydroxy-3-(phosphonooxy)propanal;Gliceraldehido-3-fosfato;Glyceraldehyde 3-(dihydrogen phosphate);Glycerinaldehyd-3-phosphat;Glyzerinaldehyd-3-phosphat;(2-hydroxy-3-oxopropyl) dihydrogen phosphoric acid;Glyceraldehyde 3-(dihydrogen phosphoric acid);Glyceraldehyde-3-phosphoric acidPW_C000869Glyc3P102781781259071475935151688316012800225770142537709713277935111120734122121183124123334135123754118125784297125949299127239205127409388721NADHMDB0000902NAD (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]1OC21H27N7O14P2InChI=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)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-N1-[(2R,3R,4S,5R)-5-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy)(hydroxy)phosphoryl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium663.4251663.109121631-2.5281-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium0-1FDB0223093-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_C000721NAD140415033538651101114211344312735146654222949277917283529310794807184813184819284902649603151679552381035334111536011254691235482125559013556101185696100573810858271415912147594215160241556072157607616163851646917867721176890160701218870971637174205719720674051987459222824122683592259085224118192161232224913006298130183001325622342404322426193157710413277120133772091347737033177650336776673347770233277709130779151137798334778406356800063688069011993825124110552388112750166112853941199291221199524061201714071208344191209844081211594251212421261212594291218173831226143841227421201231304471231411361234194551235493741237314601238124431238294641243703981251871211253192971253424791255304811258062991258254901259244821265154951267654801268855011272785071273835021280893901283603911284283951407571851441Phosphoric acidHMDB0002142Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is a mineral acid with the chemical formula H3PO4. Alternatively, orthophosphoric acid molecules can combine with themselves to form a variety of compounds referred to as phosphoric acids in a more general way. For a discussion of these, see Phosphoric acids and Phosphates. Appears to exist only as a food additive and produced synthetically. --Wikipedia.7664-38-2C00009100426078979OP(O)(O)=OH3O4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)NBIIXXVUZAFLBC-UHFFFAOYSA-Nphosphoric acid97.995297.9768950963phosphoric acid0-2FDB013380Acide phosphorique (french);Acido fosforico [italian];Acidum phosphoricum;Diphosphate tetrasodium;Fosforzuuroplossingen [dutch];Marphos;Nfb;Ortho- phosphoric acid;Orthophosphoric acid;Phosphoric acid (acd/name 4.0);Phosphorsaeure;Phosphorsaeureloesungen [german];Sodium pyrophosphate;Sodium pyrophosphate decahydrate;Sodium pyrophosphate decahydrate biochemica;Sonac;Tetra-sodium pyrophosphate;Tetrasodium pyrophosphate decahydrate;Tetrasodium pyrophosphate 10-hydrate;White phosphoric acid;[po(oh)3];Acide phosphorique;H3po4;Phosphate;Phosphorsaeureloesungen;OrthophosphatePW_C001441PhosfrA171844044831315924316782190249191054856359131475943151689116011782198118282131182921611852277126383177105132773301337747333377779111780001127827235678706331787073348067113580677119119918122120126124120157407120344406120367412121383419121900383121902408122858118122994120123014446123942455124453398124455374125308297125493299125518481125664479126056490126855205127030388127053206127159501127508507983Glyceric acid 1,3-biphosphateHMDB00012701,3-Bisphosphogylcerate (1,3BPG), also known as PGAP, is a 3-carbon organic molecule present in most, if not all living creatures. It primarily exists as a metabolic intermediate in glycolysis during respiration. 1,3BPG have been recognized as regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. 1,3BPG concentration in erythrocytes changes in a number of pathological conditions, such as Inherited Phosphoglycerate kinase deficiency in erythrocytes (involved in the synthesis and breakdown of 1,3 BPG). (PMID 3555887). 1,3-bisphosphoglycerate is the anion form of bisphosphoglyceric acid. It is phosphorylated at the number 1 and 3 carbons. The result of this phosphorylation gives 1,3BPG important biological properties such as the ability to phosphorylate ADP to form the energy storage molecule ATP.(wikipedia).1981-49-3C00236683DPG663O[C@H](COP(O)(O)=O)C(=O)OP(O)(O)=OC3H8O10P2InChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1LJQLQCAXBUHEAZ-UWTATZPHSA-N{[(2R)-2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid266.0371265.9592695-1.4451,3-bisphospho-D-glycerate0-4FDB0225241,3-biphosphoglycerate;1,3-biphosphoglyceric acid;1,3-bis-phosphoglycerate;1,3-bisphosphoglycerate;1,3-diphosphateglycerate;1,3-diphosphoglycerate;13-dpg;2-hydroxy-3-(phosphonooxy)-propanoate;2-hydroxy-3-(phosphonooxy)-propanoic acid;2-hydroxy-3-(phosphonooxy)-propanoic acid 1-anhydride with phosphorate;2-hydroxy-3-(phosphonooxy)-propanoic acid 1-anhydride with phosphoric acid;3-p-glyceroyl-p;3-phospho-d-glyceroyl phosphate;3-phospho-d-glyceroyl-phosphate;3-phosphoglyceroyl phosphate;3-phosphoglyceroyl-p;3-phosphoglyceroyl-phosphate;Dpg;Glycerate 1,3-biphosphate;Glycerate 1,3-bisphosphate;Glycerate 1,3-diphosphate;Glyceric acid 1,3-biphosphate;P-glyceroyl-p;Phosphoglyceroyl-pPW_C000983GlyABp104182253259141475944151689216077106132780291111207541221211881241233511351237591181257852971259562991272402051274143881144NADHHMDB0001487NADH 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_C001144NADH143415334908648101115212755146954223049278117283629310994806184812184821284904649593151699552401035332111535811254661235479125559313556981005737108582914159151475945151602715560791616387164721786771117689316070111887099163717220571952067462222824422683602259086224118091981182121612320249130032981301530013255223424033224261831577107132771231337720813477371331776513367766833477700332777071307791711377986347800093688069111993822124110549388112854941158381181199554061201724071203781221209864081211624251212441261216934291218183831226163841227451201231274471231381361235513741237344601238144431242424641243713981251891211253454791255314811257622971258082991259264821265164951267674801268885011273855021280903901283623911284293951407591856443-Phosphoglyceric acidHMDB00008073-phosphoglyceric acid (3PG) is a 3-carbon molecule that is a metabolic intermediate in both glycolysis and the Calvin cycle. This chemical is often termed PGA when referring to the Calvin cycle. In the Calvin cycle, two glycerate 3-phosphate molecules are reduced to form two molecules of glyceraldehyde 3-phosphate (GALP). (wikipedia).820-11-1C0059772417050G3P704OC(COP(O)(O)=O)C(O)=OC3H7O7PInChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)OSJPPGNTCRNQQC-UHFFFAOYSA-N2-hydroxy-3-(phosphonooxy)propanoic acid186.0572185.99293909-0.954phosphoglycerate0-3FDB0222553-(dihydrogen phosphate)glycerate;3-(dihydrogen phosphate)glyceric acid;3-glycerophosphorate;3-glycerophosphoric acid;3-p-d-glycerate;3-p-glycerate;3-pga;3-pg;3-phospho-(r)-glycerate;3-phospho-d-glycerate;3-phospho-glycerate;3-phospho-glyceric acid;3-phosphoglycerate;3-phosphoglyceric acid;D-(-)-3-phosphoglyceric acid;D-glycerate 3-phosphate;G3p;Glycerate 3-phosphate;Glycerate-3-p;Glyceric acid 3-phosphate;Phosphoglycerate;Dl-glycerate 3-phosphate;Glycerate 3-phosphates;3-(dihydrogen phosphoric acid)glyceric acid;2-hydroxy-3-phosphonooxypropanoate;Dl-glyceric acid 3-phosphoric acid;Glyceric acid 3-phosphoric acid;Glyceric acid 3-phosphatesPW_C000644G3P20518225725743117591714759481516897160835822542623322771111327803311112119212412138612212376311812394513512596029912741738818702-Phospho-D-glyceric acidHMDB00033912-Phospho-D-glycerate or 2PG is an intermediate in gluconeogenesis. It is a glyceric acid which serves as the substrate in the ninth step of glycolysis. 2PG is converted by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. More specifically, 2PG can be generated from Glycerate-3-phosphate via phosphoglycerate mutase or from phosphoenolpyrvate via alpha enolase.C00631439278178352-PG388411DB01709OC[C@@H](OP(O)(O)=O)C(O)=OC3H7O7PInChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1GXIURPTVHJPJLF-UWTATZPHSA-N(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid186.0572185.99293909-0.964(+-)-2-phosphoglycerate0-3FDB001407(2r)-3-hydroxy-2-(phosphonooxy)propanoate;(2r)-3-hydroxy-2-(phosphonooxy)propanoic acid;2-phospho-d-glycerate;2-phospho-d-glyceric acid;3-d-hydroxy-2-phosphonooxy-propanoate;3-d-hydroxy-2-phosphonooxy-propanoic acid;D-glycerate 2-phosphate;2-phospho-(r)-glycerate;D-glyceric acid 2-phosphoric acid;2-phospho-(r)-glyceric acidPW_C0018702PDG2263259181475949151689916077113132121194124123765118125962299127418388180Phosphoenolpyruvic acidHMDB0000263Phosphoenolpyruvate (PEP) is an important chemical compound in biochemistry. It has a high energy phosphate bond, and is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells. In gluconeogenesis, PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of 1 guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis. (wikipedia).138-08-9C00074100544897PHOSPHO-ENOL-PYRUVATE980DB01819OC(=O)C(=C)OP(O)(O)=OC3H5O6PInChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)DTBNBXWJWCWCIK-UHFFFAOYSA-N2-(phosphonooxy)prop-2-enoic acid168.042167.982374404-1.103phosphoenolpyruvic acid0-3FDB0014512-hydroxy-acrylic acid dihydrogen phosphate;2-phosphonooxyprop-2-enoate;2-phosphonooxyprop-2-enoic acid;P-enol-pyruvate;Pep;PhosphoenolpyruvatePW_C000180Pep4198226522396459191475950151617910869011601192016411931225427153157711413277308111779631331203211221211961241212134061229761351237661181237831201256482971259632991274193881275162051420WaterHMDB0002111Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).7732-18-5C0000196215377937OH2OInChI=1S/H2O/h1H2XLYOFNOQVPJJNP-UHFFFAOYSA-Nwater18.015318.0105646861water00FDB013390Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;WasserPW_C001420H2O5589491095139415131621448113526156242865210691207703382318838210943113774914655415904320182425322226786027274627781728052931437031647236346145983647273749419350302751567519597521410052279452361035297105531911153431135355112540211054701235483125549212655071275534130553711455411295591135560811856221085691657591405778101584114358531465877107589095591014759401516032155605915760871616123163613315962151621816664771786507180660015267131176840188688816071622057181207719320672112117228213723821472432157295198735021673882107401212746722274922247500190758817082012258237226841416292652611850277119221641201128112213285122502861226428712327249125202271263265126932901270529112715292130072981301930013025301130373021326122313327294153403084232731542695318436913227691429377019253771021327713113377215134773783317739733277471333775161157753633477628336777223377775934177816343779823477807132978235352782423537827035679113360800143688003937080591228806561199383038394794384110557390110639391115844398119879232119915122119963406120008407120046408120113124120365412120430405120438409120606415120794414121158425121240429121351121121381419121607434122118382122384436122753120122797374122804443123012446123064376123072137123131447123142136123162448123231451123384450123730460123810464123940455124165469124670399124938471124945472125305297125353479125386481125424482125480299125682483125707478125745487126054490126238495126273484126764480126896501126963502127017388127177208127199209127227504127506507127576515127836389128082395128176513140674790140675834140755185164Pyruvic acidHMDB0000243Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).127-17-3C00022106032816PYRUVATE1031DB00119CC(=O)C(O)=OC3H4O3InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)LCTONWCANYUPML-UHFFFAOYSA-N2-oxopropanoic acid88.062188.0160439940.181pyruvic acid0-1FDB0082932-oxopropanoate;2-oxopropanoic acid;2-oxopropionate;2-oxopropionic acid;Acetylformate;Acetylformic acid;Bts;Pyroracemate;Pyroracemic acid;Pyruvate;A-ketopropionate;A-ketopropionic acid;Alpha-ketopropionate;Alpha-ketopropionic acid;2-ketopropionic acid;2-oxopropansaeure;2-oxopropionsaeure;Acide pyruvique;Alpha-oxopropionsaeure;Brenztraubensaeure;Ch3cocooh;2-ketopropionate;α-ketopropionate;α-ketopropionic acid;A-oxopropionsaeure;α-oxopropionsaeurePW_C000164Pyr172204422811813144950145726536510354051175440118544412055661325570133589395592014759511516022155606715660741616126160638316467178651017765328574572227495220820022512622311529224915349187731011177972346779783277809011280004368800423678069513511287994115683121119950406120011124120175122120878407121148423121154424123454119123720458123726459125340479125390299125534297125854481126883501126931388127067205127858206457PotassiumHMDB0000586Potassium is an essential electrolyte. Potassium balance is crucial for regulating the excitability of nerves and muscles and so critical for regulating contractility of cardiac muscle. Although the most important changes seen in the presence of deranged potassium are cardiac, smooth muscle is also affected with increasing muscle weakness, a feature of both hyperkalaemia and hypokalaemia. Physiologically, it exists as an ion in the body. Potassium (K+) is a positively charged electrolyte, cation, which is present throughout the body in both intracellular and extracellular fluids. The majority of body potassium, >90%, are intracellular. It moves freely from intracellular fluid (ICF) to extracellular fluid (ECF) and vice versa when adenosine triphosphate increases the permeability of the cell membrane. It is mainly replaced inside or outside the cells by another cation, sodium (Na+). The movement of potassium into or out of the cells is linked to certain body hormones and also to certain physiological states. Standard laboratory tests measure ECF potassium. Potassium enters the body rapidly during food ingestion. Insulin is produced when a meal is eaten; this causes the temporary movement of potassium from ECF to ICF. Over the ensuing hours, the kidneys excrete the ingested potassium and homeostasis is returned. In the critically ill patient, suffering from hyperkalaemia, this mechanism can be manipulated beneficially by administering high concentration (50%) intravenous glucose. Insulin can be added to the glucose, but glucose alone will stimulate insulin production and cause movement of potassium from ECF to ICF. The stimulation of alpha receptors causes increased movement of potassium from ICF to ECF. A noradrenaline infusion can elevate serum potassium levels. An adrenaline infusion, or elevated adrenaline levels, can lower serum potassium levels. Metabolic acidosis causes a rise in extracellular potassium levels. In this situation, excess of hydrogen ions (H+) are exchanged for intracellular potassium ions, probably as a result of the cellular response to a falling blood pH. Metabolic alkalosis causes the opposite effect, with potassium moving into the cells. (PMID: 17883675).24203-36-9C0023881329103K%2b791DB01345[K+]KInChI=1S/K/q+1NPYPAHLBTDXSSS-UHFFFAOYSA-Npotassium(1+) ion39.098338.9637068610potassium(1+) ion11FDB003521K+;Kalium;Potassium;Potassium (k+);Potassium (ion);Potassium cation;Potassium ion;Potassium ion (k+);Potassium ion (k1+);Potassium ion(+);Potassium ion(1+);Potassium monocation;Potassium(+);Potassium(1+);Potassium(1+) ion;Potassium(i) cation;K(+)PW_C000457K+5738931191926220951530336631617231627136135136146159211475952151690216011810198152223067702322577115132776101117824132678246353120484122121198124123105135123768118124944452124949472125860297125965299127322205127421388140680834140681790140687781463Hydrogen carbonateHMDB0000595Bicarbonate, or hydrogen carbonate, is a simple single carbon molecule that plays surprisingly important roles in diverse biological processes. Among these are photosynthesis, the Krebs cycle, whole-body and cellular pH regulation, and volume regulation. Since bicarbonate is charged it is not permeable to lipid bilayers. Mammalian membranes thus contain bicarbonate transport proteins to facilitate the specific transmembrane movement of HCO3(-). Bicarbonate ion is an anion that consists of one central carbon atom surrounded by three oxygen atoms in a trigonal planar arrangement, with a hydrogen atom attached to one of the oxygens. The bicarbonate ion carries a negative one formal charge and is the conjugate base of carbonic acid, H2CO3. The carbonate radical is an elusive and strong one-electron oxidant. Bicarbonate in equilibrium with carbon dioxide constitutes the main physiological buffer. The bicarbonate-carbon dioxide pair stimulates the oxidation, peroxidation and nitration of several biological targets. The demonstration that the carbonate radical existed as an independent species in aqueous solutions at physiological pH and temperature renewed the interest in the pathophysiological roles of this radical and related species. The carbonate radical has been proposed to be a key mediator of the oxidative damage resulting from peroxynitrite production, xanthine oxidase turnover and superoxide dismutase1 peroxidase activity. The carbonate radical has also been proposed to be responsible for the stimulatory effects of the bicarbonate-carbon dioxide pair on oxidations mediated by hydrogen peroxide/transition metal ions. The ultimate precursor of the carbonate radical anion being bicarbonate, carbon dioxide, peroxymonocarbonate or complexes of transition metal ions with bicarbonate-derived species remains a matter of debate. The carbonate radical mediates some of the pathogenic effects of peroxynitrite. The carbonate radical as the oxidant produced from superoxide dismutase (EC 1.15.1.1, SOD1) peroxidase activity. Peroxymonocarbonate is a biological oxidant, whose existence is in equilibrium with hydrogen peroxide and bicarbonate. (PMID: 17505962, 17215880).71-52-3C0028876917544HCO3749OC(O)=OCH2O3InChI=1S/CH2O3/c2-1(3)4/h(H2,2,3,4)BVKZGUZCCUSVTD-UHFFFAOYSA-Ncarbonic acid62.024862.000393930.572carbonic acid0-1FDB022134Bicarbonate;Bicarbonate (hco3-);Bicarbonate anion;Bicarbonate ion;Bicarbonate ion (hco31-);Bicarbonate ions;Carbonate;Carbonate (hco31-);Carbonate ion (hco31-);Carbonic acid;Hydrocarbonate(1-);Hydrogen carbonate;Hydrogen carbonate (hco3-);Hydrogen carbonate anion;Hydrogen carbonate ion;Hydrogen carbonate ion (hco3-);Hydrogencarbonate;Hydrogentrioxocarbonate;Monohydrogen carbonate;[co2(oh)](-);Acid carbonate;Hco3(-);Hydrogen carbonic acid;Acid carbonic acid;Bicarbonic acid;Bicarbonic acid ionPW_C000463HCO322416878239332397226131531457053911035445120557113360491556110161649417874822229092224779591127863013278762111800293681199934061212094071214361221215571241237791191239941351241151181253724791260592971263602991265414811269145011275112051279223881281142061104PhosphateHMDB0001429Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.14265-44-2C00009106118367CPD-85871032OP(O)(O)=OH3O4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)NBIIXXVUZAFLBC-UHFFFAOYSA-Nphosphoric acid97.995297.9768950963phosphoric acid0-2DBMET00532FDB022617Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ionPW_C001104Pi2448488145818188312980317631417674925001027294727374631292931667236366138512342492244753150312751587520797521610053171115351112538110354471205543129557313356051355625108569365848143585514659111475941151604015561001616294107648717866911016714117684218868891607161205718920672122117306198738921074022127436163747522281962258258227101182411013425711748132117611151177321311904170119271641201428112728290132632233481917422553044235031542435318436923227701825377194293772171347794033677966130780483327805732978245353786693318002236889279308938313839479638411055839011064039111323594115845398116206109119982406120069122120699407121057124121216125121268429121352121121409123121423382121852405123304119123621118123786136123838464123968447123981399124405376124948472125362479125446297125774481125954299126221478126594300126604298126723484126904501127413388127783209128166395128177513128315389148Oxalacetic 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_C000148Oaa2549691115109931109421113216888537110354481205574133603315560881616478178746822275132247517151837222083782251174411711891160127072911271729243792322775081327753311377538334779581127800911178290345800153688070013511996440612004840812006212612018012212041912412081541812120740712279937412281344312305511812340045412377711912535447912542648212543930112553729712580148912580729912689750112696550212697720712707020512725650612726138820BiotinHMDB0000030Biotin is an enzyme co-factor present in minute amounts in every living cell. Biotin is also known as vitamin H or B7 or coenzyme R. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. Biotin has been recognized as an essential nutrient. Our biotin requirement is fulfilled in part through diet, through endogenous reutilization of biotin and perhaps through capture of biotin generated in the intestinal flora. The utilization of biotin for covalent attachment to carboxylases and its reutilization through the release of carboxylase biotin after proteolytic degradation constitutes the 'biotin cycle'. Biotin deficiency is associated with neurological manifestations, skin rash, hair loss and metabolic disturbances that are thought to relate to the various carboxylase deficiencies (metabolic ketoacidosis with lactic acidosis). It has also been suggested that biotin deficiency is associated with protein malnutrition, and that marginal biotin deficiency in pregnant women may be teratogenic. Biotin acts as a carboxyl carrier in carboxylation reactions. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lysine residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lys residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signaling, gene expression, and chromatin structure have been identified in recent years. Human cells accumulate biotin by using both the sodium-dependent multivitamin transporter and monocarboxylate transporter 1. These transporters and other biotin-binding proteins partition biotin to compartments involved in biotin signaling: cytoplasm, mitochondria, and nuclei. The activity of cell signals such as biotinyl-AMP, Sp1 and Sp3, nuclear factor (NF)-kappaB, and receptor tyrosine kinases depends on biotin supply. Consistent with a role for biotin and its catabolites in modulating these cell signals, greater than 2000 biotin-dependent genes have been identified in various human tissues. Many biotin-dependent gene products play roles in signal transduction and localize to the cell nucleus, consistent with a role for biotin in cell signaling. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to effects of biotin on gene expression. Finally, research has shown that biotinidase and holocarboxylase synthetase mediate covalent binding of biotin to histones (DNA-binding proteins), affecting chromatin structure; at least seven biotinylation sites have been identified in human histones. Biotinylation of histones appears to play a role in cell proliferation, gene silencing, and the cellular response to DNA repair. Roles for biotin in cell signaling and chromatin structure are consistent with the notion that biotin has a unique significance in cell biology. (PMID: 15992684, 16011464).58-85-5C0012017154815956BIOTIN149962DB00121[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2C10H16N2O3SInChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1YBJHBAHKTGYVGT-ZKWXMUAHSA-N5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid244.311244.088163078-2.3035-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid0-1FDB014510(+)-biotin;(+)-cis-hexahydro-2-oxo-1h-thieno[3,4]imidazole-4-valerate;(+)-cis-hexahydro-2-oxo-1h-thieno[3,4]imidazole-4-valeric acid;(3as,4s,6ar)-hexahydro-2-oxo-1h-thieno[3,4-d]imidazole-4-valerate;(3as,4s,6ar)-hexahydro-2-oxo-1h-thieno[3,4-d]imidazole-4-valeric acid;-(+)-biotin;1swk;1swn;1swr;5-(2-oxohexahydro-1h-thieno[3,4-d]imidazol-4-yl)pentanoate;5-(2-oxohexahydro-1h-thieno[3,4-d]imidazol-4-yl)pentanoic acid;Biodermatin;Bioepiderm;Bios ii;Bios h;Biotin;Coenzyme r;D(+)-biotin;D-(+)-biotin;D-biotin;D-biotin factor s;Factor s;Factor s (vitamin);Hexahydro-2-oxo-1h-thieno(3,4-d)imidazole-4-pentanoate;Hexahydro-2-oxo-1h-thieno(3,4-d)imidazole-4-pentanoic acid;Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1h-thieno[3,4-d]imidazole-4-pentanoate;Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1h-thieno[3,4-d]imidazole-4-pentanoic acid;Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1h-thieno[3,4-d]imidazole-4-pentanoate;Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1h-thieno[3,4-d]imidazole-4-pentanoic acid;Lutavit h2;Meribin;Rovimix h 2;Vitamin b7;Vitamin h;Vitamin-h;Cis-(+)-tetrahydro-2-oxothieno[3,4]imidazoline-4-valerate;Cis-(+)-tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid;Cis-hexahydro-2-oxo-1h-thieno(3,4)imidazole-4-valeric acid;Cis-tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid;Delta-(+)-biotin;Delta-biotin;Delta-biotin factor s;Biotina;Biotine;BiotinumPW_C000020Biotin2641358579151699322702529210152981055393103544912055461115551114557513360511556112161649617869251607484222778311327796011280031368806531351199954061201341221205034091212104071215591241231091371237801191241171181253744791255012971257184831264212991265424811269165011270382051279893881281152061027ManganeseHMDB0001333Manganese is an essential trace nutrient in all forms of life. Physiologically, it. exists as an ion in the body. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver.16397-91-4C196102785429035MN%2b325916[Mn++]MnInChI=1S/Mn/q+2WAEMQWOKJMHJLA-UHFFFAOYSA-Nmanganese(2+) ion54.93854.9380496360manganese(2+) ion22FDB003636Manganese;Manganese (ii) ion;Manganese(ii);Manganese, ion (mn2+);Manganous ion;Mn(2+);Mn2+PW_C001027Mn2+27447381486491553432271223943251314539410354501205576133605215561131616497178692616074852221188019811939225119581641247124913360151152213067705029477494111778321327796111278267356784901157852433179247293800323681199964061204011221210581241212114071212953831213784191224884051230441351236221181237811191238653981239374551250543761253754791259764951260514901260602971261582991265434811266424781269175011274293901275035071275122051277653881281162061282182091099Coenzyme AHMDB0001423Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme notable for its role in the synthesis and oxidization of fatty acids and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate, and adenosine triphosphate. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step pantothenate (vitamin B5) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK, CoaA, CoaX). In the second step, a cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC, CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD). Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier proteins and formyltetrahydrofolate dehydrogenase. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production (Wikipedia).85-61-0C0001068161146900CO-A6557CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC21H36N7O16P3SInChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1RGJOEKWQDUBAIZ-IBOSZNHHSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid767.534767.115208365-2.2210coenzyme A0-4FDB022614Acetoacetyl coenzyme a sodium salt;Coa;Coa hydrate;Coa-sh;Coash;Coenzyme a;Coenzyme a hydrate;Coenzyme a-sh;Coenzyme ash;Coenzymes a;Depot-zeel;Propionyl coa;Propionyl coenzyme a;S-propanoate;S-propanoate coa;S-propanoate coenzyme a;S-propanoic acid;S-propionate coa;S-propionate coenzyme a;Zeel;[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphatePW_C001099CoA2114386884538792289217240759241422459528132928623133421133511846181046295848421448655448796523210252471045280103547712457341085777101602315560751616384164681786930160696116269731997083188710816372931987347210745822282291519081226909022491241709215195130132991531824925488494261631576907293771191337722213477230329772921117755013277555334775631127763333677672129779961157804733278056350784133357856713079259333799743318000536880620118806273748063511980665376938283829383438398674288110555389110561390115842399115847398119951406120147405120231384120305122120634407120762117121406123121421433121521125121666429121682408121714414122404422122741120122904121122960135123965447123979468124079136124220464124265450124974375125341479125509478125579480125592484125634297126084481126549491126560482126746300126884501127046209127109391127301205127540206127667388128121508128133502128340395140751186140763185140767891940Acetyl-CoAHMDB0001206The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.72-89-9C0002444449315351ACETYL-COA392413CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC23H38N7O17P3SInChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1ZSLZBFCDCINBPY-ZSJPKINUSA-N{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid809.571809.125773051-2.279acetyl-CoA0-4FDB022491Ac-coa;Ac-coenzyme a;Ac-s-coa;Ac-s-coenzyme a;Acetyl coenzyme-a;Acetyl-coa;Acetyl-coenzyme a;Acetyl-s-coa;Acetyl-s-coenzyme a;Acetylcoenzyme-a;S-acetate coa;S-acetate coenzyme a;S-acetyl coenzyme a;Accoa;Acetyl coenzyme a;S-acetyl-coa;S-acetyl-coenzyme a;Acetylcoenzyme aPW_C000940Ac-CoA21343858842324162244652896173340114840145278103547612457331086025155607716163861647017869231607106163729119874602228245151827721012582226130122994261531577121133772911117756211277706132779941157835513478433334800073688063411980663376901241701199534061201454051203041221206324071224174081226263841227431201229591351231371181249863741252001211253434791255074781256332971265644821265724811267784801268865011270442091273942051276653881281375021281452061283743911407621851316Carbon dioxideHMDB0001967Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.124-38-9C0001128016526274O=C=OCO2InChI=1S/CO2/c2-1-3CURLTUGMZLYLDI-UHFFFAOYSA-Nmethanedione44.009543.9898292440.630carbon dioxide00DBMET00423FDB014084Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744PW_C001316CO250812112044480135031864036773169520806511334316384917452255117314470528310353201115750108577110159681006026155607816164711786637107692219070171607035163706118871632057308198733321374612227530210821522582231519158249118492771190817012464226126882904262631543523318769942937712213377170132774703337773911277750129777633417807713478405356784273347894133179227130800083688067511980717135948363841132913911155491211199544061200891221201554071203644121205564141208334191209221241209914081212841251215053831227441201230114461231904501234184551234891181235563741238551361240633981253444791254602971255164811258244901258702991259314821262804801268875011270522061272775071273313881273905021407981851060Thiamine pyrophosphateHMDB0001372Thiamine pyrophosphate is the active form of thiamine, and it serves as a cofactor for several enzymes involved primarily in carbohydrate catabolism. The enzymes are important in the biosynthesis of a number of cell constituents, including neurotransmitters, and for the production of reducing equivalents used in oxidant stress defenses and in biosyntheses and for synthesis of pentoses used as nucleic acid precursors. The chemical structure of TPP is that of an aromatic methylaminopyrimidine ring, linked via a methylene bridge to a methylthiazolium ring with a pyrophosphate group attached to a hydroxyethyl side chain. In non-enzymatic model studies it has been demonstrated that the thiazolium ring can catalyse reactions which are similar to those of TPP-dependent enzymes but several orders of magnitude slower. Using infrared and NMR spectrophotometry it has been shown that the dissociation of the proton from C2 of the thiazolium ring is necessary for catalysis; the abstraction of the proton leads to the formation of a carbanion (ylid) with the potential for a nucleophilic attack on the carbonyl group of the substrate. In all TPP-dependent enzymes the abstraction of the proton from the C2 atom is the first step in catalysis, which is followed by a nucleophilic attack of this carbanion on the substrate. Subsequent cleavage of a C-C bond releases the first product with formation of a second carbanion (2-greek small letter alpha-carbanion or enamine). The formation of this 2-greek small letter alpha-carbanion is the second feature of TPP catalysis common to all TPP-dependent enzymes. Depending on the enzyme and the substrate(s), the reaction intermediates and products differ. Methyl-branched fatty acids, as phytanic acid, undergo peroxisomal beta-oxidation in which they are shortened by 1 carbon atom. This process includes four steps: activation, 2-hydroxylation, thiamine pyrophosphate dependent cleavage and aldehyde dehydrogenation. In the third step, 2-hydroxy-3-methylacyl-CoA is cleaved in the peroxisomal matrix by 2-hydroxyphytanoyl-CoA lyase (2-HPCL), which uses thiamine pyrophosphate (TPP) as cofactor. The thiamine pyrophosphate dependence of the third step is unique in peroxisomal mammalian enzymology. Human pathology due to a deficient alpha-oxidation is mostly linked to mutations in the gene coding for the second enzyme of the sequence, phytanoyl-CoA hydroxylase (EC 1.14.11.18). (PMID: 12694175, 11899071, 9924800).154-87-0C00068113295322-(alpha-lactyl)-thpp1100CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1NC12H19N4O7P2SInChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1AYEKOFBPNLCAJY-UHFFFAOYSA-O3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium425.314425.044967696-3.484thiamin pyrophosphate1-1FDB022584Tpp;Thpp;Thaimine pyrophosphate;Thiamin diphosphate;Thiamin pyrophosphate;Thiamin-ppi;Thiamine diphosphate;Thiamine pyrophosphate;Thiamine-ppi;Thiamine-pyrophosphate;Thiamin diphosphoric acid;Thiamine(1+) diphosphoric acid;Thiamin pyrophosphoric acid;Thiamine diphosphoric acidPW_C001060ThiamPP205410753119781271517362536610360281556080161638816473178746322212806225771241337828511278423334790181117917513280010368119956406120802407120902122120982408121537124122746120123388119123473135123547374124095118125346479125922482126094481126802299126889501127381502127549206128400388769LipoamideHMDB0000962Lipoamide is the oxidized form of glutathione. (PMID:8957191). Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acid's functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH2) to an amino group. Lipoamide forms a thioester bond, oxidizing the disulfide bond, with acetaldehyde (pyruvate after it has been decarboxylated). It then transfers the acetaldehyde group to CoA which can then continue in the TCA cycle. (Wikipedia). Lipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG:C00248). It is generated from dihydrolipoamide via the enzyme dihydrolipoamide dehydrogenase (EC:1.8.1.4) and then converted to S-glutaryl-dihydrolipoamide via the enzyme oxoglutarate dehydrogenase (EC:1.2.4.2).940-69-2C0024886317460LIPOAMIDE840NC(=O)CCCCC1CCSS1C8H15NOS2InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)FCCDDURTIIUXBY-UHFFFAOYSA-N5-(1,2-dithiolan-3-yl)pentanamide205.341205.059505487-3.311lipoamide00FDB0223401,2-dithiolane-3-pentanamide;5-(1,2-dithiolan-3-yl)-pentanamide;5-(1,2-dithiolan-3-yl)pentanamide;5-(1,2-dithiolan-3-yl)valeramide;5-(dithiolan-3-yl)valeramide;Dl-lipoamide;Dl-6-thioctic amide;Lipamide;Lipoacin;Lipoamid;Lipoicin;Lipozyme;Lypoaran;Pathoclon;Thioami;Thioctamid;Thioctamide;Thioctic acid amide;Thioctic acid amide (jan);Thiotomin;Ticolin;Vitamin n;Alpha-lipoate;Alpha-lipoic acid;Alpha-lipoic acid amide;A-lipoate amide;A-lipoic acid amide;Alpha-lipoate amide;α-lipoate amide;α-lipoic acid amide;Thioctate amidePW_C000769Lipoamd2024107331734246678536710360291556081161638916474178746422277125133782861127917313280011368119957406120803407121535124122747120123389119124093118125347479126078481126890501127534206964FADHMDB0001248FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).146-14-5C0001664397516238FAD559059DB03147CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2C27H33N9O15P2InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1VWWQXMAJTJZDQX-UYBVJOGSSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid785.5497785.157134455-2.279flavine-adenine dinucleotide0-3FDB0225111h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;AdeflavinPW_C000964FAD999114518681923216425317628288251884021188141489421612291622492133582536223723264602364688314741134758104881652681035285102533511154961265511127561311860301556054156608216161161626390164751786499179666610770391637175205732121374652227487223907622411818216118872151189921112296225123282491244315112519227125952261271029112720292130293011304130243623318770802937712613377152134775011137750711277518115775413347761513277726337780543297837534578930331792223367927235880012368800343698071411911995840611999938412005140812010740712043240512045312212049012412127842912129841812141738212148938312274812012277612112280237412282344312306637612308713512316644812384946412386845412397639912404739812534847912537848012542948212547448112569729712597948912610729912627748412689150112692039112696850212698720712701120612731020912743250612760238812784038914079018514079918663Citric acidHMDB0000094Citric acid (citrate) is a weak acid that is formed in the tricarboxylic acid cycle or that may be introduced with diet. The evaluation of plasma citric acid is scarcely used in the diagnosis of human diseases. On the contrary urinary citrate excretion is a common tool in the differential diagnosis of kidney stones, renal tubular acidosis and it plays also a role in bone diseases. The importance of hypocitraturia should be considered with regard to bone mass, urine crystallization and urolithiasis. (PMID 12957820) The secretory epithelial cells of the prostate gland of humans and other animals posses a unique citrate-related metabolic pathway regulated by testosterone and prolactin. This specialized hormone-regulated metabolic activity is responsible for the major prostate function of the production and secretion of extraordinarily high levels of citrate. The key regulatory enzymes directly associated with citrate production in the prostate cells are mitochondrial aspartate aminotransferase, pyruvate dehydrogenase, and mitochondrial aconitase. testosterone and prolactin are involved in the regulation of the corresponding genes associated with these enzymes. The regulatory regions of these genes contain the necessary response elements that confer the ability of both hormones to control gene transcription. Protein kinase c (PKC) is the signaling pathway for the prolactin regulation of the metabolic genes in prostate cells. testosterone and prolactin regulation of these metabolic genes (which are constitutively expressed in all mammalian cells) is specific for these citrate-producing cells. (PMID 12198595) Citric acid is found in citrus fruits, most concentrated in lemons and limes, where it can comprise as much as 8% of the dry weight of the fruit. Citric acid is a natural preservative and is also used to add an acidic (sour) taste to foods and soft drinks. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Intolerance to citric acid in the diet is known to exist. Little information is available as the condition appears to be rare, but like other types of food intolerance it is often described as a "pseudo-allergic" reaction.77-92-9C001581978290430769CIT305DB04272OC(=O)CC(O)(CC(O)=O)C(O)=OC6H8O7InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)KRKNYBCHXYNGOX-UHFFFAOYSA-N2-hydroxypropane-1,2,3-tricarboxylic acid192.1235192.02700261-0.264citric acid0-3FDB0125862-hydroxy-1,2,3-propanetricarboxylate;2-hydroxy-1,2,3-propanetricarboxylic acid;3-carboxy-3-hydroxypentane-1,5-dioate;3-carboxy-3-hydroxypentane-1,5-dioic acid;Aciletten;Anhydrous citrate;Anhydrous citric acid;Chemfill;Citraclean;Citrate;Citretten;Citric acid;Citro;E 330;Hydrocerol a;Kyselina citronova;Suby g;Uro-trainer;Beta-hydroxytricarballylate;Beta-hydroxytricarballylic acid;2-hydroxytricarballylic acid;Citronensaeure;E330;H3cit;2-hydroxytricarballylatePW_C000063CA219424152537210360341556089161647917874692227713213379053132800163681117128119965406122397124122754120124967118125355479126538299126898501128111388122L-Lactic acidHMDB0000190Lactic acid is an organic acid. It is a chiral molecule, consisting of two optical isomers, L-lactic acid and D-lactic acid, with the L-isomer being the most common in living organisms. Lactic acid plays a role in several biochemical processes and is produced in the muscles during intense activity. In animals, L-lactate is constantly produced from pyruvate via the enzyme lactate dehydrogenase (LDH) in a process of fermentation during normal metabolism and exercise. It does not increase in concentration until the rate of lactate production exceeds the rate of lactate removal. This is governed by a number of factors, including monocarboxylate transporters, lactate concentration, the isoform of LDH, and oxidative capacity of tissues. The concentration of blood lactate is usually 1-2 mmol/L at rest, but can rise to over 20 mmol/L during intense exertion. There are some indications that lactate, and not glucose, is preferentially metabolized by neurons in the brain of several mammalian species, including mice, rats, and humans. Glial cells, using the lactate shuttle, are responsible for transforming glucose into lactate, and for providing lactate to the neurons. Lactate measurement in critically ill patients has been traditionally used to stratify patients with poor outcomes. However, plasma lactate levels are the result of a finely tuned interplay of factors that affect the balance between its production and its clearance. When the oxygen supply does not match its consumption, organisms adapt in many different ways, up to the point when energy failure occurs. Lactate, being part of the adaptive response, may then be used to assess the severity of the supply/demand imbalance. In such a scenario, the time to intervention becomes relevant: early and effective treatment may allow tissues and cells to revert to a normal state, as long as the oxygen machinery (i.e. mitochondria) is intact. Conversely, once the mitochondria are deranged, energy failure occurs even in the presence of normoxia. The lactate increase in critically ill patients may, therefore, be viewed as an early marker of a potentially reversible state (PMID: 16356243). When present in sufficiently high levels, lactic acid can act as an oncometabolite, an immunosuppressant, an acidogen, and a metabotoxin. An oncometabolite is a compound that promotes tumor growth and survival. An immunosuppressant reduces or arrests the activity of the immune system. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of lactic acid are associated with at least a dozen inborn errors of metabolism, including 2-methyl-3-hydroxybutyryl CoA dehydrogenase deficiency, biotinidase deficiency, fructose-1,6-diphosphatase deficiency, glycogen storage disease type 1A (GSD1A) or Von Gierke disease, glycogenosis type IB, glycogenosis type IC, glycogenosis type VI, Hers disease, lactic acidemia, Leigh syndrome, methylmalonate semialdehyde dehydrogenase deficiency, pyruvate decarboxylase E1 component deficiency, pyruvate dehydrogenase complex deficiency, pyruvate dehydrogenase deficiency, and short chain acyl CoA dehydrogenase deficiency (SCAD deficiency). Locally high concentrations of lactic acid or lactate are found near many tumors due to the upregulation of lactate dehydrogenase (PMID: 15279558). Lactic acid produced by tumors through aerobic glycolysis acts as an immunosuppressant and tumor promoter (PMID: 23729358). Indeed, lactic acid has been found to be a key player or regulator in the development and malignant progression of a variety of cancers (PMID: 22084445). A number of studies have demonstrated that malignant transformation is associated with an increase in aerobic cellular lactate excretion. Lactate concentrations in various carcinomas (e.g. uterine cervix, head and neck, colorectal region) at first diagnosis of the disease, can be relatively low or extremely high (up to 40 µmol/g) in different individual tumors or within the same lesion (PMID: 15279558). High molar concentrations of lactate are correlated with a high incidence of distant metastasis. Low lactate tumors (< median of approximately 8 µmol/g) are associated with both an overall longer and disease-free survival compared to high lactate lesions (lactate > approximately 8 µmol/g). Lactate-induced secretion of hyaluronan by tumor-associated fibroblasts creates a milieu favourable for cell migration and metastases (PMID: 22084445). An acidic environment (pH 6-6.5), which is common in many tumors, allows tumor cells to evade the immune response, and therefore allows them to grow unchecked. Locally high concentrations of lactic acid are known to markedly impede the function of normal immune cells and will lead to a loss of T-cell function of human tumor-infiltrating lymphocytes (PMID: 22084445). Lactic acid is also an organic acid and acts as a general acidogen. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development.79-33-4C00186107689422L-LACTATE96860C[C@H](O)C(O)=OC3H6O3InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1JVTAAEKCZFNVCJ-REOHCLBHSA-N(2S)-2-hydroxypropanoic acid90.077990.0316940582(α)-lactate0-1FDB003294(+)-lactate;(+)-lactic acid;(s)-(+)-2-hydroxypropanoate;(s)-(+)-2-hydroxypropanoic acid;(s)-2-hydroxypropanoate;(s)-2-hydroxypropanoic acid;(s)-2-hydroxypropionate;(s)-2-hydroxypropionic acid;(s)-2-hydroxy-propanoate;(s)-2-hydroxy-propanoic acid;(s)-lactate;(s)-lactic acid;(alpha)-lactate;(alpha)-lactic acid;1-hydroxyethane 1-carboxylate;1-hydroxyethane 1-carboxylic acid;1-hydroxyethanecarboxylate;1-hydroxyethanecarboxylic acid;2-hydroxypropanoate;2-hydroxypropanoic acid;2-hydroxypropionate;L-(+)- lactic acid;L-2-hydroxypropanoate;L-2-hydroxypropanoic acid;Lactate;Lactic acid;Milk acid;Sarcolactic acid;A-hydroxypropanoate;A-hydroxypropanoic acid;A-hydroxypropionate;A-hydroxypropionic acid;Alpha-hydroxypropanoate;Alpha-hydroxypropanoic acid;Alpha-hydroxypropionate;Alpha-hydroxypropionic acid;(s)-(+)-lactic acid;L-(+)-alpha-hydroxypropionic acid;L-(+)-lactic acid;L-lactic acid;L-milchsaeurePW_C000122Lactate1717823992505015779641327876411111783311412121412412143812212267740912378411812399613512525213712606229712678829912681048312751420512838538812840920840034Hydrogen 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+21546708753157883184831116214632614645422314927801742502242544245471045761846947052411035327111535311256261085639107569910057201055742117596314760371556070157609316161301596232166648317866011526692101684318869101877100163716820571912067453219745422074722227525213753221075582127572160759017081952258218151824322684131628420224913919591552491191516412015281121812851224628612266287125212271325722313325294153303084232931542354318424013224240531242454320769122937713613377210134773723317780411477955132779903277799134778379345799291308001936880387310803883048072211993823124948233831105503881128559411328039011553739811553911811585633611620510911997340612019340712054912212059340912117042412117142512256941812261538412268712512275812012318313512321813712374245912374346012514145412518812112527313612535947912555048112573048312573629712580929912651749512671748912676648012682330012690250112721320812830850612836139112843039514069288214069388314069916714070716814071514140742788140743597140760185125Isocitric acidHMDB0000193The citrate oxidation to isocitrate is catalyzed by the enzyme aconitase. Human prostatic secretion is remarkably rich in citric acid and low aconitase activity will therefore play a significant role in enabling accumulation of high citrate levels (PubMed ID 8115279).320-77-4C00311119830887threo-d(s)-iso-citrate1161OC(C(CC(O)=O)C(O)=O)C(O)=OC6H8O7InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)ODBLHEXUDAPZAU-UHFFFAOYSA-N1-hydroxypropane-1,2,3-tricarboxylic acid192.1235192.02700261-0.564isocitric acid0-3FDB0032811-hydroxy-1,2,3-propanetricarboxylate;1-hydroxy-1,2,3-propanetricarboxylic acid;1-hydroxypropane-1,2,3-tricarboxylate;1-hydroxypropane-1,2,3-tricarboxylic acid;1-hydroxytricarballylate;1-hydroxytricarballylic acid;3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylate;3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid;3-carboxy-2,3-dideoxy-pentarate;3-carboxy-2,3-dideoxy-pentaric acid;D-isocitrate;I-cit;Isocitrate;Threo-d(s)-iso-citrate;Threo-ds-isocitratePW_C000125I-cita224450642537410360351556091161648117874702227713413380017368117827132119971406122672124122756120125247118125389479126805299126930501128403388407114Fe-4SHMDB0061380Tetrakis(λ¹-iron(1+) ion) tetrasulfane tetrasulfanide belongs to the class of inorganic compounds known as transition metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a transition metal.33723S.S.S.S.[SH-].[SH-].[SH-].[SH-].[Fe+].[Fe+].[Fe+].[Fe+]Fe4H12S8InChI=1S/4Fe.8H2S/h;;;;8*1H2/q4*+1;;;;;;;;/p-4WBBXSFIKFJDGSG-UHFFFAOYSA-Jtetrakis(lambda1-iron(1+) ion) tetrasulfane tetrasulfanide491.96491.6102140tetrakis(lambda1-iron(1+) ion) tetrasulfane tetrasulfanide01PW_C0407114Fe-4S47383485985051450652540311060601576124163650818074932241261816477160112780031118004037080681135117797133117828132120009407120161122122658406122673124122784119125233120125248118125387481125522297126790479126806299126928206127057205128387501128404388134Oxoglutaric 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_C000134AKG1524231414146849918673311108421263514475014552614675453751035414117543811855641326008147603615560691576092161648217865308574712227515224751915182092258374220118631981268128977054253771351337748111177523112777461297796734577970346779763277798434778425334800183688069413511316294119972406120022124120084407120174122120552414120814418120989408121146423121152424121160425122757120122831119123186450123399454123554374123718458123724459123732460125357479125400299125455481125533297125800489125929482126900501126940388126993206127066205127255506127388502808Succinyl-CoAHMDB0001022Succinyl-CoA is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by α-ketoglutarate dehydrogenase (EC 1.2.4.2) through decarboxylation, and is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (EC 6.2.1.5). Succinyl-CoA may be an end product of peroxisomal beta-oxidation of dicarboxylic fatty acids; the identification of an apparently specific succinyl-CoA thioesterase (ACOT4, EC 3.1.2.3, hydrolyzes succinyl-CoA) in peroxisomes strongly suggests that succinyl-CoA is formed in peroxisomes. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A, thereby regulating levels of these compounds. (PMID: 16141203).604-98-8C00091439161153803-METHYLBENZYLSUCCINYL-COA388307CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=OC25H40N7O19P3SInChI=1S/C25H40N7O19P3S/c1-25(2,20(38)23(39)28-6-5-14(33)27-7-8-55-16(36)4-3-15(34)35)10-48-54(45,46)51-53(43,44)47-9-13-19(50-52(40,41)42)18(37)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,37-38H,3-10H2,1-2H3,(H,27,33)(H,28,39)(H,34,35)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t13-,18-,19-,20?,24-/m1/s1VNOYUJKHFWYWIR-FZEDXVDRSA-N4-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-4-oxobutanoic acid867.607867.131252359-2.19104-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-4-oxobutanoic acid0-5FDB022375Coa s-(hydrogen succinate);Coa s-succinate;Coenzyme a s-(hydrogen succinate);Coenzyme a s-succinate;S-(hydrogen butanedioate;S-(hydrogen butanedioate) coa;S-(hydrogen butanedioate) coenzyme a;S-(hydrogen butanedioic acid;S-succinoylcoenzyme a;Suc-co-a;Suc-coa;Succ-coa;Succ-coenzyme a;Succ-s-coa;Succ-s-coenzyme a;Succ-s-coenzyme-a;Succ-coenzyme-a;Succino-1-yl-coenzyme a;Succinyl coa;Succinyl coenzyme a;Succinyl-s-coa;Succinyl-s-coenzyme a;Succinyl-s-coenzyme-a;Succinylcoenzyme-a;Succinylcoenzyme aPW_C000808Suc-CoA23341055336692537810360391556097161648517870151607361163747422277140133781011127857613280021368119978406120769407122014124122763120123365119124568118125358479126164299126306481126901501127868206936Guanosine diphosphateHMDB0001201Guanosine 5'-(trihydrogen diphosphate). A guanine nucleotide containing two phosphate groups esterified to the sugar moiety. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase guanine. GDP is the product of GTP dephosphorylation by GTPases, e.g. the G-proteins that are involved in signal transduction.146-91-8C00035897717552GDP-4-DEHYDRO-6-DEOXY-D-MANNOSE8630NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1C10H15N5O11P2InChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1QGWNDRXFNXRZMB-UUOKFMHZSA-N[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid443.2005443.024329371-2.007{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid0-3FDB0224875'-gdp;Gdp;Guanosine 5'-(trihydrogen pyrophosphate);Guanosine 5'-diphosphate;Guanosine 5'-pyrophosphate;Guanosine mono(trihydrogen diphosphate);Guanosine pyrophosphate;Guanosine-5'-diphosphate;Guanosine-diphosphate;Ppg;Guanosine diphosphate;Guanosine 5'-diphosphoric acidPW_C000936GDP83823841762142391241547350078553821036041155610116164881787476222117541151177121111823198127272901339515169322177142133775461117795213280023368800803088012216489115253119983406120068122121205124121847405122766120122820135123775118124400376125363479125445297126905501126984205174Succinic acidHMDB0000254Succinic acid is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. Succinate dehydrogenase (SDH) plays an important role in the mitochondria, being both part of the respiratory chain and the Krebs cycle. SDH with a covalently attached FAD prosthetic group, binds enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the whole Krebs cycle. The succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate. (PMID 16143825) Mutations in the four genes encoding the subunits of the mitochondrial respiratory chain succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntington's disease. (PMID 11803021).110-15-6C00042111015741SUC1078DB00139OC(=O)CCC(O)=OC4H6O4InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)KDYFGRWQOYBRFD-UHFFFAOYSA-Nbutanedioic acid118.088118.026608680.252succinic acid0-2FDB0019311,2-ethanedicarboxylate;1,2-ethanedicarboxylic acid;1,4-butanedioate;1,4-butanedioic acid;Amber acid;Asuccin;Dihydrofumarate;Dihydrofumaric acid;Katasuccin;Succinate;Wormwood acid;Acide butanedioique;Acide succinique;Acidum succinicum;Bernsteinsaeure;Butandisaeure;Butanedionic acid;E363;Ethylenesuccinic acid;Hooc-ch2-ch2-cooh;Spirit of amber;Butanedionate;EthylenesuccinatePW_C000174Succini15232394502185078676311265542551753831036042155610216164541076455108648917867641176836166736216374552197456220747722211866198121421511325922342368318423693154240232277143133772131347748311177738112777491297842633480024368807211191128463081134281119984406120192407120385122120555414120990408122565384122767120123029135123189450123555374125138121125364479125549481125930482126713480126906501127082206127389502128304391986Guanosine triphosphateHMDB0001273Guanosine triphosphate (GTP) is a guanine nucleotide containing three phosphate groups esterified to the sugar moiety. GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA.86-01-1C00044683015996GTP6569NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1C10H16N5O14P3InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1XKMLYUALXHKNFT-UUOKFMHZSA-N({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid523.1804522.990659781-1.708triphosphate, guanosine0-3FDB0225275'-gtp;Gtg;Gtp;Guanosine 5'-(tetrahydrogen triphosphate);Guanosine 5'-triphosphate;Guanosine 5'-triphosphorate;Guanosine 5'-triphosphoric acid;Guanosine triphosphate;Guanosine mono(tetrahydrogen triphosphate) (ester);H4gtp;Guanosine-5'-triphosphatePW_C000986GTP81824041939240911441537350068553841036043155610316164901787478222117531151176919811981151127252906932717696222577144133775441117795113280025368800883088012116489113253119985406120066122121204124122768120122818135123774118125365479125443297126480299126907501126982205128051388846Coenzyme Q10HMDB0001072Coenzyme Q10 (ubiquinone) is a naturally occurring compound widely distributed in animal organisms and in humans. The primary compounds involved in the biosynthesis of ubiquinone are 4-hydroxybenzoate and the polyprenyl chain. An essential role of coenzyme Q10 is as an electron carrier in the mitochondrial respiratory chain. Moreover, coenzyme Q10 is one of the most important lipophilic antioxidants, preventing the generation of free radicals as well as oxidative modifications of proteins, lipids, and DNA, it and can also regenerate the other powerful lipophilic antioxidant, alpha-tocopherol. Antioxidant action is a property of the reduced form of coenzyme Q10, ubiquinol (CoQ10H2), and the ubisemiquinone radical (CoQ10H*). Paradoxically, independently of the known antioxidant properties of coenzyme Q10, the ubisemiquinone radical anion (CoQ10-) possesses prooxidative properties. Decreased levels of coenzyme Q10 in humans are observed in many pathologies (e.g. cardiac disorders, neurodegenerative diseases, AIDS, cancer) associated with intensive generation of free radicals and their action on cells and tissues. In these cases, treatment involves pharmaceutical supplementation or increased consumption of coenzyme Q10 with meals as well as treatment with suitable chemical compounds (i.e. folic acid or B-group vitamins) which significantly increase ubiquinone biosynthesis in the organism. Estimation of coenzyme Q10 deficiency and efficiency of its supplementation requires a determination of ubiquinone levels in the organism. Therefore, highly selective and sensitive methods must be applied, such as HPLC with UV or coulometric detection. For a number of years, coenzyme Q (CoQ10 in humans) was known for its key role in mitochondrial bioenergetics; later studies demonstrated its presence in other subcellular fractions and in plasma, and extensively investigated its antioxidant role. These two functions constitute the basis on which research supporting the clinical use of CoQ10 is founded. Also at the inner mitochondrial membrane level, coenzyme Q is recognized as an obligatory co-factor for the function of uncoupling proteins and a modulator of the transition pore. Furthermore, recent data reveal that CoQ10 affects expression of genes involved in human cell signalling, metabolism, and transport and some of the effects of exogenously administered CoQ10 may be due to this property. Coenzyme Q is the only lipid soluble antioxidant synthesized endogenously. In its reduced form, CoQH2, ubiquinol, inhibits protein and DNA oxidation but it is the effect on lipid peroxidation that has been most deeply studied. Ubiquinol inhibits the peroxidation of cell membrane lipids and also that of lipoprotein lipids present in the circulation. Dietary supplementation with CoQ10 results in increased levels of ubiquinol-10 within circulating lipoproteins and increased resistance of human low-density lipoproteins to the initiation of lipid peroxidation. Moreover, CoQ10 has a direct anti-atherogenic effect, which has been demonstrated in apolipoprotein E-deficient mice fed with a high-fat diet. (PMID: 15928598, 17914161).303-98-0C11378528191546245UBIQUINONE-104445197COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=OC59H90O4InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+ACTIUHUUMQJHFO-UPTCCGCDSA-N2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione863.3435862.683911368-6.650coenzyme-Q1000FDB014621(all-e)-2,3-dimethoxy-5-methyl-6-(3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenyl)-2,5-cyclohexadiene-1,4-dione;(all-e)-2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione;2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-benzoquinone;2-[(2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl- 2,5-cyclohexadiene-1,4-dione;4-ethyl-5-fluoropyrimidine;Aqua q 10l10;Aqua q10;Bio-quinon;Bio-quinone q10;Coq10;Coenzyme q10;Ensorb;Kaneka q10;Kudesan;Li-q-sorb;Liquid-q;Neuquinon;Neuquinone;Puresorb q 40;Q 10aa;Q-gel;Q-gel 100;Ubidecarenone;Ubiquinone 10;Ubiquinone 50;Ubiquinone q10;Ubiquinone-10;Unbiquinone;Unispheres q 10;2-((all-e)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-benzoquinone;2-[(2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone;Adelir;All-trans-ubiquinone;Coq;Q;Q 199;Q10;UbiquinonePW_C000846Coq25217425142505245396102605315661151626498179748622377151134783713458003336911780713311999838412256241812266040612277512112513545412523512012537748012671048912679247912691939112830150612839050188Fumaric acidHMDB0000134Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. (wikipedia).110-17-8C001222188378818012FUM10197150DB04299OC(=O)\C=C\C(O)=OC4H4O4InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+VZCYOOQTPOCHFL-OWOJBTEDSA-N(2E)-but-2-enedioic acid116.0722116.010958616-0.682fumaric acid0-2FDB003291(2e)-but-2-enedioate;(2e)-but-2-enedioic acid;(e)-2-butenedioate;(e)-2-butenedioic acid;2-(e)-butenedioate;2-(e)-butenedioic acid;Allomaleate;Allomaleic acid;Boletate;Boletic acid;Fc 33;Fumarate;Fumaric acid;Lichenate;Lichenic acid;Sodium fumarate;Trans-1,2-ethylenedicarboxylate;Trans-1,2-ethylenedicarboxylic acid;Trans-2-butenedioate;Trans-2-butenedioic acid;Trans-butenedioate;Trans-butenedioic acid;(2e)-2-butenedioic acid;E297;Fumarsaeure;Trans-but-2-enedioic acid;(2e)-2-butenedioate;Trans-but-2-enedioatePW_C000088Fumarat1028254172004250534538810260471566107162645810764591086492179676311768371667480223906515111804198127132904240032242496318424973157714813477466111791071328002736911780813311998938412004312212159912412266140612277212112279413512415711812523612012536948012542129712679347912691139112696020512756538812839150140098QH(2)HMDB0059661QH(2), also known as ubiquinol, belongs to the class of organic compounds known as ubiquinols. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methylbenzene-1,4-diol moiety to which an isoprenyl group is attached at ring position 2(or 6). QH(2) is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, QH(2) is primarily located in the membrane (predicted from logP) and cytoplasm. QH(2) exists in all living organisms, ranging from bacteria to humans. In humans, QH(2) is involved in the congenital lactic acidosis pathway, the citric Acid cycle pathway, and the oncogenic action OF 2-hydroxyglutarate pathway. QH(2) is also involved in several metabolic disorders, some of which include fumarase deficiency, cancer (via the Warburg effect), pyruvate dehydrogenase deficiency (e3), and mitochondrial complex II deficiency. Qh(2) is part of the Oxidative phosphorylation, Cardiac muscle contraction, Alzheimer\'s disease, Parkinson\'s disease, and Huntington\'s disease pathways. It is a substrate for: Cytochrome b-c1 complex subunit Rieske, mitochondrial.44792017976394877COC1=C(O)C(C)=C(CC=C(C)C)C(O)=C1OCC14H20O4InChI=1S/C14H20O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6,15-16H,7H2,1-5H3TVLSKGDBUQMDPR-UHFFFAOYSA-N2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol252.3062252.136159128-2.9222,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol00Ubiquinol(1)PW_C040098QH(2)2551750544539710260551566117162650017974882237715313480035369117809133120000384122662406122777121125237120125379480126794479126921391128392501932FADHHMDB0001197FADH is the reduced form of flavin adenine dinucleotide (FAD). FAD is synthesized from riboflavin and two molecules of ATP. Riboflavin is phosphorylated by ATP to give riboflavin 5-phosphate (FMN). FAD is then formed from FMN by the transfer of an AMP moiety from a second molecule of ATP. FADH is generated in each round of fatty acid oxidation, and the fatty acyl chain is shortened by two carbon atoms as a result of these reactions; because oxidation is on the beta carbon, this series of reactions is called the beta-oxidation pathway. In the citric acid cycle FADH is involved in harvesting of high-energy electrons from carbon fuels; citric acid cycle itself neither generates a large amount of ATP nor includes oxygen as a reactant. Instead, the citric acid cycle removes electrons from acetyl CoA and uses these electrons to form FADH. (Biochemistry. Berg, Jeremy M. Tymoczko, John L. and Stryer, Lubert. New York: W. H. Freeman and Co. 2002.).1910-41-4C0135244601317877FADH2393487CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=C(N2)C(=O)NC(=O)N1C27H35N9O15P2InChI=1S/C27H35N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1YPZRHBJKEMOYQH-UYBVJOGSSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid787.5656787.172784519-2.3711fadh(.)0-2FDB0224831,5-dihydro-fad;1,5-dihydro-p-5-ester with adenosine;1,5-dihydro-riboflavin 5'-(trihydrogen diphosphate) p'->5'-ester with adenosine;Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(d-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine 5'-(trihydrogen pyrophosphate), 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(d-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine 5'-{3-[d-ribo-5-(7,8-dimethyl-2,4-dioxo-1,2,3,4,5,10-tetrahydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen diphosphate};Adenosine 5-(trihydrogen pyrophosphate);Adenosine pyrophosphate 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(d-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine pyrophosphate, 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(d-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine pyrophosphate, 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(d-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Benzo[g]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv;Benzo[gr]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv;Dihydro-fad;Dihydroflavine-adenine dinucleotide;Fadh2;Fda;Flavin adenine dinucleotide (reduced);Flavin adenine dinucleotide reduced;Reduced flavine adenine dinucleotidePW_C000932FADH2561710453149042505545398102605615661181626501179748922390772241252322712527249771541347852534580036369117810133120001384121299418122663406122778121123869454125238120125380480125980489126795479126922391127433506128393501405582Fe-2SHMDB0061344Bis(λ²-iron(2+) ion) disulfane tetrasulfanide belongs to the class of inorganic compounds known as transition metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a transition metal.S.S.[SH-].[SH-].[SH-].[SH-].[Fe++].[Fe++]Fe2H8S6InChI=1S/2Fe.6H2S/h;;6*1H2/q2*+2;;;;;;/p-4MZMMVZPHZTYDNI-UHFFFAOYSA-Jbis(lambda2-iron(2+) ion) disulfane tetrasulfanide312.11311.7648990bis(lambda2-iron(2+) ion) disulfane tetrasulfanide02PW_C0405582Fe2S37422401284257174389346265475431482994837285056454971265512127704616013030301130423027771511377727337783771347838613279207112117811133121586407121795124122567384122664406123152443123167448124144119124346118125140121125239120126189299126715480126796479127680388128306391128394501101L-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_C000101Malate26241098317218238725387103573510860461556106161645310764911787451219745222074792224245531842456315771471337876611179051132790571128002636811998840612144112212239412412240140712277112012399913512496411812497111912536847912606629712653529912654648112691050112751920512810838812811820695L-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_C000095Glu162443658119113841641496991105421448501456261462545323111534411354151175439118556513256311075632108585910560061476071157619194653185683818768441887092727093717165205718220775142247518151820822583732201179219811855161120042221262131126832891269729042348315423493184284532077020253773321337752511277971346779773277798134778291345806491351200231241200401221200864071203474061206921261208164181211474231211534241211574251228331191229971201232994431234014541237194581237254591237294601254012991254182971254574811256674791257693011258024891269413881269952061271625011272575061407388414073959735AmmoniaHMDB0000051Ammonia is a colourless alkaline gas and is one of the most abundant nitrogen-containing compounds in the atmosphere. It is an irritant with a characteristic pungent odor that is widely used in industry. Inasmuch as ammonia is highly soluble in water and, upon inhalation, is deposited in the upper airways, occupational exposures to ammonia have commonly been associated with sinusitis, upper airway irritation, and eye irritation. Acute exposures to high levels of ammonia have also been associated with diseases of the lower airways and interstitial lung. Small amounts of ammonia are naturally formed in nearly all tissues and organs of the vertebrate organism. Ammonia is both a neurotoxin and a metabotoxin. In fact, it is the most common endogenous neurotoxin. A neurotoxin is a compound that causes damage to neural tissue and neural cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Ammonia is recognized to be central in the pathogenesis of a brain condition known as hepatic encephalopathy, which arises from various liver diseases and leads to a build up ammonia in the blood (hyperammonemia). More than 40% of people with cirrhosis develop hepatic encephalopathy. Part of the neurotoxicity of ammonia arises from the fact that it easily crosses the blood-brain barrier and is absorbed and metabolized by the astrocytes, a population of cells in the brain that constitutes 30% of the cerebral cortex. Astrocytes use ammonia when synthesizing glutamine from glutamate. The increased levels of glutamine lead to an increase in osmotic pressure in the astrocytes, which become swollen. There is increased activity of the inhibitory gamma-aminobutyric acid (GABA) system, and the energy supply to other brain cells is decreased. This can be thought of as an example of brain edema. The source of the ammonia leading to hepatic encephalopathy is not entirely clear. The gut produces ammonia, which is metabolized in the liver, and almost all organ systems are involved in ammonia metabolism. Colonic bacteria produce ammonia by splitting urea and other amino acids, however this does not fully explain hyperammonemia and hepatic encephalopathy. The alternative explanation is that hyperammonemia is the result of the intestinal breakdown of amino acids, especially glutamine. The intestines have significant glutaminase activity, predominantly located in the enterocytes. On the other hand, intestinal tissues only have a little glutamine synthetase activity, making it a major glutamine-consuming organ. In addition to the intestine, the kidney is an important source of blood ammonia in patients with liver disease. Ammonia is also taken up by the muscle and brain in hepatic coma, and there is confirmation that ammonia is metabolized in muscle. Excessive formation of ammonia in the brains of Alzheimer's disease patients has also been demonstrated, and it has been shown that some Alzheimer's disease patients exhibit elevated blood ammonia concentrations. Ammonia is the most important natural modulator of lysosomal protein processing. Indeed, there is strong evidence for the involvement of aberrant lysosomal processing of beta-amyloid precursor protein (beta-APP) in the formation of amyloid deposits. Inflammatory processes and activation of microglia are widely believed to be implicated in the pathology of Alzheimer's disease. Ammonia is able to affect the characteristic functions of microglia, such as endocytosis, and cytokine production. Based on these facts, an ammonia-based hypothesis for Alzheimer's disease has been suggested (PMID: 17006913, 16167195, 15377862, 15369278). Chronically high levels of ammonia in the blood are associated with nearly twenty different inborn errors of metabolism including: 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, 3-methyl-crotonylglycinuria, argininemia, argininosuccinic aciduria, beta-ketothiolase deficiency, biotinidase deficiency, carbamoyl phosphate synthetase deficiency, carnitine-acylcarnitine translocase deficiency, citrullinemia type I, hyperinsulinism-hyperammonemia syndrome, hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, isovaleric aciduria, lysinuric protein intolerance, malonic aciduria, methylmalonic aciduria, methylmalonic aciduria due to cobalamin-related disorders, propionic acidemia, pyruvate carboxylase deficiency, and short chain acyl CoA dehydrogenase deficiency (SCAD deficiency). Many of these inborn errors of metabolism are associated with urea cycle disorders or impairment of amino acid metabolism. High levels of ammonia in the blood (hyperammonemia) lead to the activation of NMDA receptors in the brain. This results in the depletion of brain ATP, which in turn leads to the release of glutamate. Ammonia also leads to the impairment of mitochondrial function and calcium homeostasis, thereby decreasing ATP synthesis. Excess ammonia also increases the formation of nitric oxide (NO), which in turn reduces the activity of glutamine synthetase, and thereby decreases the elimination of ammonia in the brain (PMID: 12020609). As a neurotoxin, ammonia predominantly affects astrocytes. Disturbed mitochondrial function and oxidative stress, factors implicated in the induction of the mitochondrial permeability transition, appear to be involved in the mechanism of ammonia neurotoxicity. Ammonia can also affect the glutamatergic and GABAergic neuronal systems, the two prevailing neuronal systems of the cortical structures. All of these effects can lead to irreversible brain damage, coma, and/or death. Infants with urea cycle disorders and hyperammonemia initially exhibit vomiting and increasing lethargy. If untreated, seizures, hypotonia (poor muscle tone, floppiness), respiratory distress (respiratory alkalosis), and coma can occur. Adults with urea cycle disorders and hyperammonemia will exhibit episodes of disorientation, confusion, slurred speech, unusual and extreme combativeness or agitation, stroke-like symptoms, lethargy, and delirium. Ammonia also has toxic effects when an individual is exposed to ammonia solutions. Acute exposure to high levels of ammonia in air may be irritating to skin, eyes, throat, and lungs and cause coughing and burns. Lung damage and death may occur after exposure to very high concentrations of ammonia. Swallowing concentrated solutions of ammonia can cause burns in the mouth, throat, and stomach. Splashing ammonia into eyes can cause burns and even blindness.7664-41-7C0001422216134AMMONIA217NH3NInChI=1S/H3N/h1H3QGZKDVFQNNGYKY-UHFFFAOYSA-Nammonia17.030517.0265491011ammonia01FDB003908Ammonia anhydrous;Ammonia inhalant;Ammonia solution strong [usan];Ammonia water;Ammoniak;Liquid ammonia;Am-fol;Ammonia;Ammonia (conc 20% or greater);Ammonia gas;Ammonia solution;Ammonia solution strong (nf);Ammonia water (jp15);Ammoniac [french];Ammoniaca [italian];Ammoniacum gummi;Ammoniak [german];Ammoniak kconzentrierter;Ammoniakgas;Ammonium ion;Amoniak [polish];Anhydrous ammonia;Aromatic ammonia vaporole;Azane;Nh(3);Nh3;Nitro-sil;Primaeres amin;Sekundaeres amin;Spirit of hartshorn;Tertiaeres amin;[nh3];Ammoniac;Amoniaco;R-717;Ammonia solution strongPW_C000035NH39791125133814244382479135501414685425332225723533811160161477022160717720511786198118482771188521512708291127182927696622577046294773291337734313277469333774991137753933477597115779853477799311278072329792442938065013580657119116203109119921122120049408120053126120136407120343406120363412120462405121046124121161425122119382122800374122805443122993120123010446123096376123610118123733460124671399125311297125427482125431301125502481125663479125708478126102299126274484126966502126970207127039206127158501127200209127600388127837389500L-GlutamineHMDB0000641Glutamine (Gln) is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide; it is formed by replacing a side-chain hydroxyl of glutamic acid with an amine functional group. glutamine is found in foods high in proteins, such as fish, red meat, beans, and dairy products. glutamine is a supplement that is used in weightlifting, bodybuilding, endurance and other sports, as well as by those who suffer from muscular cramps or pain particularly elderly people. The main use of glutamine within the diet of either group is as a means of replenishing the body's stores of amino acids that have been used during exercise or everyday activities. Studies which are looking into problems with excessive consumption of glutamine thus far have proved inconclusive. However, normal supplementation is healthy mainly because glutamine is supposed to be supplemented after prolonged periods of exercise (for example, a workout or exercise in which amino acids are required for use) and replenishes amino acid stores; this being the main reason glutamine is recommended during fasting or for people who suffer from physical trauma, immune deficiencies, or cancer. There is a significant body of evidence that links glutamine-enriched diets with intestinal effects; aiding maintenance of gut barrier function, intestinal cell proliferation and differentiation, as well as generally reducing septic morbidity and the symptoms of Irritable Bowel Syndrome. The reason for such "cleansing" properties is thought to stem from the fact that the intestinal extraction rate of glutamine is higher than that for other amino acids, and is therefore thought to be the most viable option when attempting to alleviate conditions relating to the gastrointestinal tract. These conditions were discovered after comparing plasma concentration within the gut between glutamine-enriched and non glutamine-enriched diets. However, even though glutamine is thought to have "cleansing" properties and effects, it is unknown to what extent glutamine has clinical benefits, due to the varied concentrations of glutamine in varieties of food. It is also known that glutamine has various effects in reducing healing time after operations. Hospital waiting times after abdominal surgery are reduced by providing parenteral nutrition regimens containing amounts of glutamine to patients. Clinical trials have revealed that patients on supplementation regimes containing glutamine have improved nitrogen balances, generation of cysteinyl-leukotrienes from polymorphonuclear neutrophil granulocytes and improved lymphocyte recovery and intestinal permeability (in postoperative patients) - in comparison to those who had no glutamine within their dietary regime; all without any side-effects. (http://en.wikipedia.org/wiki/glutamine).56-85-9C00064596118050GLN5746DB00130N[C@@H](CCC(N)=O)C(O)=OC5H10N2O3InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1ZDXPYRJPNDTMRX-VKHMYHEASA-N(2S)-2-amino-4-carbamoylbutanoic acid146.1445146.069142196-0.173L-glutamine00FDB012164(2s)-2,5-diamino-5-oxopentanoate;(2s)-2,5-diamino-5-oxopentanoic acid;(2s)-2-amino-4-carbamoylbutanoate;(2s)-2-amino-4-carbamoylbutanoic acid;(s)-2,5-diamino-5-oxopentanoate;(s)-2,5-diamino-5-oxopentanoic acid;2-aminoglutaramic acid;Cebrogen;Glavamin;Glumin;Glutamic acid 5-amide;Glutamic acid amide;Glutamine;L-(+)-glutamine;L-2-aminoglutaramic acid;L-2-aminoglutaramidic acid;L-glutamic acid 5-amide;L-glutamic acid gamma-amide;L-glutamid;L-glutamide;L-glutamin;L-glutamine;L-glutaminsaeure-5-amid;Levoglutamid;Levoglutamida;Levoglutamide;Levoglutamidum;Levoglutamina;Polyglutamine;Stimulina;Gamma-glutamine;Q;Glutamate 5-amide;Glutamate amidePW_C000500Gln61844342701230211556581075659108606815768461666847383902251179319812692290423523184235331577016253772961117733313378395132791641147926411680652135113207941162071091200381221203484061212194091219611241229981201237891371245141181254162971256684791263592991268124831269562051271635011277183881284112081019D-Erythrose 4-phosphateHMDB0001321D-Erythrose 4-phosphate is a phosphorylated derivative of erythrose that serves as an important intermediate in the pentose phosphate pathway. It is also used in phenylalanine, tyrosine and tryptophan biosynthesis, and it plays a role in vitamin B6 metabolism (KEGG).585-18-2C0027912235748153ERYTHROSE-4P109096O[C@H](COP(O)(O)=O)[C@@H](O)C=OC4H9O7PInChI=1S/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/t3-,4+/m0/s1NGHMDNPXVRFFGS-IUYQGCFVSA-N[(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid200.0838200.008589154-0.9344-O-phosphono-D-erythrose0-2FDB001614D-erythrose 4-po4;D-erythrose 4-phosphate;D-erythrose-4-p;D-erythrose-4-phosphate;Erythrose 4-po4;Erythrose 4-phosphate;Erythrose-4-p;Erythrose-4-phosphate;Erythrose-4p;Threose 4-phosphate;4-o-phosphono-d-erythrose;Erythose-4-phosphatePW_C001019D-Ery4P17842618510861961076197117736816011921164119322254272432277182132122192124124744118126352299127914388843D-Sedoheptulose 7-phosphateHMDB0001068D-Sedoheptulose 7-phosphate is an intermediate of the Pentose phosphate pathway (PPP) that has two functions: the generation of NADPH for reductive syntheses and oxidative stress responses within cells, and the formation of ribose residues for nucleotide and nucleic acid biosynthesis. (PMID 16055050)It is formed by transketolase and acted upon (degraded) by transaldolase. Sedoheptulose 7-phosphate can be increased in the blood of patients affected with a transaldolase deficiency (TALDO1; EC 2.2.1.2). (PMID 12881455) Sedoheptulose is a ketoheptose, a monosaccharide with seven carbon atoms and a ketone functional group. It is one of the few heptoses found in nature. (wikipedia).2646-35-7C002812283355915721D-SEDOHEPTULOSE-7-P17216052OC[C@]1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1OC7H15O10PInChI=1S/C7H15O10P/c8-2-7(12)6(11)5(10)4(9)3(17-7)1-16-18(13,14)15/h3-6,8-12H,1-2H2,(H2,13,14,15)/t3-,4-,5-,6+,7+/m1/s1CBIDVWSRUUODHL-OVHBTUCOSA-N{[(2R,3S,4R,5S,6S)-3,4,5,6-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}phosphonic acid290.161290.040283681-0.987[(2R,3S,4R,5S,6S)-3,4,5,6-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]methoxyphosphonic acid0-2FDB0224077-(dihydrogen phosphate) sedoheptulose;D-sedoheptulose 7-phosphate;D-sedoheptulose-7-p;D-sedoheptulose-7-phosphate;Heptulose-7-phosphate;Sedoheptulose 7-phosphate;Sedoheptulose-7-p;Sedoheptulose-7-phosphatePW_C000843D-SH7P17822771801321221901241247421181263502991279123881191D-Ribose 5-phosphateHMDB0001548D-Ribose 5-phosphate is an important intermediate metabolite in the Pentose phosphate pathway (KEGG, map00030) and in the Purine metabolism pathway (KEGG, map00230). The intracellular ribose 5-phosphate concentration is an important determinant of the rate of de novo purine synthesis. (PMID 6699001).4300-28-1C0011743916752742RIBOSE-5P388313O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1OC5H11O8PInChI=1S/C5H11O8P/c6-3-2(1-12-14(9,10)11)13-5(8)4(3)7/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5+/m1/s1KTVPXOYAKDPRHY-AIHAYLRMSA-N{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy}phosphonic acid230.1098230.01915384-0.845α-D-ribose 5-phosphate0-2FDB001615D-ribose 5-phosphate;D-ribose-5-p;D-ribose-5-phosphate;D-ribose-5-phosphorate;D-ribose-5-phosphoric acid;Ribose-5-p;Ribose-5-phosphate;Ribose-5-phosphorate;Ribose-5-phosphoric acid;Ribose-5p;D-ribose 5'-phosphate;Ribose 5-phosphate;D-ribose 5'-phosphoric acid;D-ribofuranose 5-phosphoric acid;D-ribose 5-phosphoric acid;Ribose 5-phosphoric acidPW_C001191DRib-5P175821838811790198132952257717113278680111121870122122183124124423135124735118126340299127904388691Xylulose 5-phosphateHMDB0000868Xylulose 5-phosphate (Xu-5-P) is a metabolite of the hexose monophosphate pathway that activates protein phosphatase 2A to mediate the acute effects of carbohydrate feeding on the glycolytic pathway, as well as the coordinate long-term control of the enzymes required for fatty acid and triglyceride synthesis. Xu-5-P is the signal for the coordinated control of lipogenesis. Feeding carbohydrate causes levels of liver glucose, Glucose-6-phosphate (Glc-6-P), and Fructose-6-phosphate (Fru-6-P) to rise. Elevation of Fru-6-P leads to elevation of Xu-5-P in reactions catalyzed by the near-equilibrium isomerases of the nonoxidative portion of the hexose monophosphate pathway (ribulose 5-phosphate (Ru5P) epimerase [EC 5.1.3.1], ribose 5-phosphate (Rib5P) isomerase [EC 5.3.1.6], transaldolase [EC 2.2.1.2], and transketolase [EC 2.2.1.1]). The elevation of Xu-5-P is the coordinating signal that both acutely activates phosphofructokinase [PFK; EC 2.7.1.11] in glycolysis and promotes the action of the transcription factor carbohydrate responsive element binding protein (ChREBP) to increase transcription of the genes for the enzymes of lipogenesis, the hexose monophosphate shunt, and glycolysis, all of which are required for the de novo synthesis of fat. (PMID 12721358).60802-29-1C0023143919016332XYLULOSE-5-PHOSPHATE388330DB04034OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=OC5H11O8PInChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5-/m1/s1FNZLKVNUWIIPSJ-RFZPGFLSSA-N{[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid230.1098230.01915384-0.955ribulose-5-phosphate0-2FDB022290D-xylulose 5-po4;D-xylulose 5-phosphate;D-xylulose-5-p;D-xylulose-5-phosphate;Xu-5-p;Xylulose 5-phosphate;Xylulose-p;Xylulose-phosphate;5-o-phosphono-d-threo-pentos-2-ulose;5-o-phosphono-d-xylulose;D-xylulose 5-phosphoric acid;D-xylulose-5-phosphoric acidPW_C000691Xyl-5-P17762132942251329815177178132122188124124740118126348299127910388479D-Ribulose 5-phosphateHMDB0000618D-Ribulose 5-phosphate belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. D-Ribulose 5-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). D-Ribulose 5-phosphate has been found in human prostate tissue, and has also been detected in multiple biofluids, such as saliva and blood. Within the cell, D-ribulose 5-phosphate is primarily located in the endoplasmic reticulum. D-Ribulose 5-phosphate exists in all living organisms, ranging from bacteria to humans. D-Ribulose 5-phosphate participates in a number of enzymatic reactions. In particular, D-Ribulose 5-phosphate can be converted into D-arabinose 5-phosphate through its interaction with the enzymes D-arabinose 5-phosphate isomerase and D-arabinose 5-phosphate isomerase 2. In addition, D-Ribulose 5-phosphate can be biosynthesized from 6-phosphogluconic acid; which is catalyzed by the enzyme 6-phosphogluconate dehydrogenase, decarboxylating. In humans, D-ribulose 5-phosphate is involved in the pentose phosphate pathway. D-Ribulose 5-phosphate is also involved in several metabolic disorders, some of which include ribose-5-phosphate isomerase deficiency, transaldolase deficiency, cancer (via the Warburg effect), and glucose-6-phosphate dehydrogenase deficiency. D-Ribulose 5-phosphate is a metabolite in the Pentose phosphate pathway, Pentose and glucuronate interconversions, and in the Riboflavin metabolism (KEGG).4151-19-3C0019943918417363RIBULOSE-5POCC(=O)[C@H](O)[C@H](O)COP(O)(O)=OC5H11O8PInChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5+/m1/s1FNZLKVNUWIIPSJ-UHNVWZDZSA-N{[(2R,3R)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid230.1098230.01915384-0.955Ara0-2FDB022145D-ribulose 5-phosphate;Erythro-pentulose 5-phosphate;Ribulose 5-phosphate;Ribulose phosphate;Alpha-d-ribose 5-phosphatePW_C000479RP174221250515113293225770152537716913212218212412473411812633929912790338810156-Phosphogluconic acidHMDB00013166-Phosphogluconic acid, also known as 6-phospho-D-gluconate or gluconate 6-phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. 6-Phosphogluconic acid is soluble (in water) and a moderately acidic compound (based on its pKa). 6-Phosphogluconic acid has been found in human adipose , epidermis and prostate tissues, and has also been detected in multiple biofluids, such as saliva and blood. Within the cell, 6-phosphogluconic acid is primarily located in the endoplasmic reticulum. 6-Phosphogluconic acid exists in all living organisms, ranging from bacteria to humans. 6-Phosphogluconic acid participates in a number of enzymatic reactions. In particular, 6-Phosphogluconic acid can be converted into D-ribulose 5-phosphate; which is catalyzed by the enzyme 6-phosphogluconate dehydrogenase, decarboxylating. In addition, 6-Phosphogluconic acid can be biosynthesized from 6-phosphonoglucono-D-lactone through the action of the enzyme 6-phosphogluconolactonase. In humans, 6-phosphogluconic acid is involved in the pentose phosphate pathway. 6-Phosphogluconic acid is also involved in several metabolic disorders, some of which include cancer (via the Warburg effect), ribose-5-phosphate isomerase deficiency, glucose-6-phosphate dehydrogenase deficiency, and transaldolase deficiency. Outside of the human body, 6-phosphogluconic acid can be found in a number of food items such as other soy product, cucumber, persimmon, and mamey sapote. This makes 6-phosphogluconic acid a potential biomarker for the consumption of these food products. Intermediate in the Pentose phosphate pathway (KEGG).921-62-0C003459149348928CPD-296182615O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=OC6H13O10PInChI=1S/C6H13O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3-,4+,5-/m1/s1BIRSGZKFKXLSJQ-SQOUGZDYSA-N(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid276.1352276.024633148-1.1276-phosphogluconic acid0-3FDB0225506-o-phosphono-d-gluconic acid;6-phospho-d-gluconate;6-phospho-d-gluconic acid;6-phosphogluconate;6-phosphogluconic acid;6-p-gluconate;D-gluconic acid 6-(dihydrogen phosphate);D-gluconic acid 6-phosphate;Gluconic acid-6-phosphatePW_C0010156-PPGA1739213292225771681321221801241247321181263372991279003888816-Phosphonoglucono-D-lactoneHMDB00011276-phosphoglucono-delta-lactone (d-6PGL) is the immediate product of the Glucose-6-phosphate dehydrogenase (G-6-PD), the first enzyme of the hexose monophosphate pathway. (PMID 3711719). The pentose-phosphate pathway provides reductive power and nucleotide precursors to the cell through oxidative and nonoxidative branches. 6-Phosphogluconolactonase is the second enzyme of the oxidative branch and catalyzes the hydrolysis of 6-phosphogluconolactones, the products of glucose 6-phosphate oxidation by glucose-6-phosphate dehydrogenase. By efficiently catalyzing the hydrolysis of d-6PGL, 6-phosphogluconolactonase prevents the reaction between d-6PGL and intracellular nucleophiles; such a reaction would interrupt the functioning of the pentose-phosphate pathway. (PMID 11457850).2641-81-8C0123643945216938D-6-P-GLUCONO-DELTA-LACTONE388559O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)OC(=O)[C@@H]1OC6H11O9PInChI=1S/C6H11O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-5,7-9H,1H2,(H2,11,12,13)/t2-,3-,4+,5-/m1/s1IJOJIVNDFQSGAB-SQOUGZDYSA-N{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid258.1199258.014068462-0.9056-phosphogluconolactone0-2FDB0224406-(dihydrogen phosphate)-(8ci)-d-gluconic acid delta-lactone;6-(dihydrogen phosphate)-(9ci)-d-gluconic acid delta-lactone;6-(dihydrogen phosphate)-d-gluconic acid delta-lactone;6-pgdl;6-phospho-d-glucono-1,5-lactone;6-phosphoglucono-delta-lactone;6-phosphogluconolactone;6-phosphonoglucono-delta-lactone;D-6-phospho-glucono-delta-lactone;D-6-phosphoglucono-delta-lactone;D-glucono-1,5-lactone 6-phosphate;D-glucono-delta-lactone-6-phosphate;Delta-gluconolactone 6-phosphate;[(2r,3s,4s,5r)-3,4,5-trihydroxy-6-oxotetrahydro-2h-pyran-2-yl]methyl dihydrogen phosphate;D-gluconic acid, delta-lactone, 6-(dihydrogen phosphate)PW_C0008816-PGDL50632132912251178231321226701241252451181268032991284013881051HydrogenHMDB0001362Hydrogen is a colorless, odorless, nonmetallic, tasteless, highly flammable diatomic gas with the molecular formula H2. With an atomic weight of 1.00794, hydrogen is the lightest element. Besides the common H1 isotope, hydrogen exists as the stable isotope Deuterium and the unstable, radioactive isotope Tritium. Hydrogen is the most abundant of the chemical elements, constituting roughly 75% of the universe's elemental mass. Hydrogen can form compounds with most elements and is present in water and most organic compounds. It plays a particularly important role in acid-base chemistry, in which many reactions involve the exchange of protons between soluble molecules. Oxidation of hydrogen, in the sense of removing its electron, formally gives H+, containing no electrons and a nucleus which is usually composed of one proton. That is why H+ is often called a proton. This species is central to discussion of acids. Under the Bronsted-Lowry theory, acids are proton donors, while bases are proton acceptors. A bare proton H+ cannot exist in solution because of its strong tendency to attach itself to atoms or molecules with electrons. However, the term 'proton' is used loosely to refer to positively charged or cationic hydrogen, denoted H+. H2 is a product of some types of anaerobic metabolism and is produced by several microorganisms, usually via reactions catalyzed by iron- or nickel-containing enzymes called hydrogenases. These enzymes catalyze the reversible redox reaction between H2 and its component two protons and two electrons. Creation of hydrogen gas occurs in the transfer of reducing equivalents produced during pyruvate fermentation to water.1333-74-0C002825883867318276ALPHA-GLUCOSE-16-BISPHOSPHATE762[H][H]H2InChI=1S/H2/h1HUFHFLCQGNIYNRP-UHFFFAOYSA-Ndihydrogen2.01592.0156500640dihydrogen00FDB016247Dihydrogen;Hydrogen;Hydrogen cation;Hydrogen gas;Hydrogen ion;Hydronium;Proton;E 949;E-949;E949;H2;Molecular hydrogenPW_C001051H2175682388226963314670495210703316370451601277415113270225785941127860313278772111113163941214481221220324071220371241240061351245861191245911181260732971261824811261882991275292051280053881283232061906β-D-Glucose 6-phosphateHMDB0003498Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in the glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways [Kegg ID: C01172]. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted to glycogen, especially if blood glucose levels are high.C0117243942717719388538O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1OC6H13O9PInChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1NBSCHQHZLSJFNQ-VFUOTHLCSA-N{[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid260.1358260.029718526-0.926β-D-glucose 6-phosphate0-2FDB023183Beta-d-glucose 6-(dihydrogen phosphate);Beta-d-glucose 6-phosphate;6-h2po3glcbeta;6-o-phosphono-beta-d-glucopyranose;Beta-d-glucose 6-phosphic acid;Beta-d-glucose-6-phosphate;B-d-glucose 6-phosphate;B-d-glucose 6-phosphoric acid;Beta-d-glucose 6-phosphoric acid;β-d-glucose 6-phosphate;β-d-glucose 6-phosphoric acid;6-o-phosphono-b-d-glucopyranose;6-o-phosphono-β-d-glucopyranose;B-d-glucose 6-(dihydrogen phosphate);B-d-glucose 6-(dihydrogen phosphoric acid);Beta-d-glucose 6-(dihydrogen phosphoric acid);β-d-glucose 6-(dihydrogen phosphate);β-d-glucose 6-(dihydrogen phosphoric acid);B-d-glucose-6-phosphate;B-d-glucose-6-phosphoric acid;Beta-d-glucose-6-phosphoric acid;β-d-glucose-6-phosphate;β-d-glucose-6-phosphoric acidPW_C001906BDGlu6P1728236492959031475931151621110862881076877160129821661329022542381318423823157709213279063336121177124122587429123749118125159464125943299127403388137064707137065280143NADPHMDB0000217Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).53-59-8C00006588618009NAD(P)5675NC(=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](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O17P3InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-N1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium743.405743.075452041-2.2281-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium0-3FDB021908Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acidPW_C000143NADP1838191376857801082418839216112916174946853147961448011453081115790108601714761321596273356778117706918871051637152205720616073172137346210756221275891708197225822015184192241181119811897211120082221215216412249286125972261265024942344315437453227691329377164132773843317739633277461130775151157762433677814334778701128071311911316594120106407120429405120450122120604408120618123121142125121277429121401124121485383123063376123084135123229374123243447123713136123848464123960118124043398125473481125694297125743482126215299126528495127010206127225502127570388128100390140709168146NADPHHMDB0000221Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).53-57-6C000052283351216474NADPH17215925NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H30N7O17P3InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1ACFIXJIJDZMPPO-NNYOXOHSSA-N{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid745.4209745.091102105-2.149nadph0-4FDB0219092'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reducedPW_C000146NADPH185819037781079658211883721609291615494687314793144797145310111578910859721476128159627135677911770681887103163715420572051607315213734521075592127591170819422582191518421224118121981189321112006222121501641224528612596226126482494234331543746322769112937716613277385331773943327746013077504112775111157762333680712119113164941201054071204254051204521221206161231211411251212754291214021241214833831230593761230861351232414471237121361238464641239611181240413981254724811256962971262142991265294951270092061275723881281013901407061682449Solute carrier family 2, facilitated glucose transporter member 2P11168Facilitative glucose transporter. This isoform likely mediates the bidirectional transfer of glucose across the plasma membrane of hepatocytes and is responsible for uptake of glucose by the beta cells; may comprise part of the glucose-sensing mechanism of the beta cell. May also participate with the Na(+)/glucose cotransporter in the transcellular transport of glucose in the small intestine and kidney.
HMDBP05474SLC2A23q26.1-q26.2CH4710521845122814162753141686661419316714222430814388051207Hexokinase-2P52789HMDBP00213HK22p13Z4635812.7.1.1221721413511601416212614166450142308100814251010191438051169751Glucose-6-phosphate isomeraseP06744
Besides it's role as a glycolytic enzyme, mammalian GPI can function as a tumor-secreted cytokine and an angiogenic factor (AMF) that stimulates endothelial cell motility. GPI is also a neurotrophic factor (Neuroleukin) for spinal and sensory neurons.
HMDBP00806GPI19q13.1AH00271015.3.1.9180525955147129838140382394141353160141813261422109991423101008142512101914378111697066-phosphofructokinase, liver typeP17858Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
HMDBP00758PFKL21q22.3BC00642212.7.1.11102281793213886829714181526918Fructose-bisphosphate aldolase BP05062In vertebrates, 3 forms of this ubiquitous glycolytic enzyme are found, aldolase A in muscle, aldolase B in liver, and aldolase C in brain. The fructose bisphosphate aldolase class of enzymes catalyze two reactions: (1) the cleavage of 6-carbon fructose 1,6-bisphosphate (FBP) into the 3-carbon products dihydroxyacetone phosphate (DHAP) and glyceraldehyde 3-phosphate (G3P) and (2) the cleavage of 6-carbon fructose 1-phosphate (F1P) the 3-carbon products glyceraldehyde and DHAP. Aldolase B, unlike the other aldolase isoenzymes, is preferentially expressed in the liver and catalyzes both reactions (showing no preference for either). Aldolases A and C both prefer FBP as a substrate molecule (PMID: 11679716).HMDBP00980ALDOB9q21.3-q22.2M1565714.1.2.132880850482595814713887129714181726659Glyceraldehyde-3-phosphate dehydrogenaseP04406Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. Participates in nuclear events including transcription, RNA transport, DNA replication and apoptosis. Nuclear functions are probably due to the nitrosylase activity that mediates cysteine S-nitrosylation of nuclear target proteins such as SIRT1, HDAC2 and PRKDC. Modulates the organization and assembly of the cytoskeleton. Facilitates the CHP1-dependent microtubule and membrane associations through its ability to stimulate the binding of CHP1 to microtubules (By similarity). Glyceraldehyde-3-phosphate dehydrogenase is a key enzyme in glycolysis that catalyzes the first step of the pathway by converting D-glyceraldehyde 3-phosphate (G3P) into 3-phospho-D-glyceroyl phosphate. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma treatment assembles into the GAIT complex which binds to stem loop-containing GAIT elements in the 3'-UTR of diverse inflammatory mRNAs (such as ceruplasmin) and suppresses their translation.
HMDBP00695GAPDH12p13BC01331011.2.1.12; 2.6.99.-1042822542595914714135816014221499914229223142315100814251710191417Phosphoglycerate kinase 1P00558In addition to its role as a glycolytic enzyme, it seems that PGK-1 acts as a polymerase alpha cofactor protein (primer recognition protein).
HMDBP01528PGK1Xq13.3AB06243212.7.2.34107235049259601479006814182226142297999261Phosphoglycerate mutase 2P15259Interconversion of 3- and 2-phosphoglycerate with 2,3-bisphosphoglycerate as the primer of the reaction. Can also catalyze the reaction of EC 5.4.2.4 (synthase) and EC 3.1.3.13 (phosphatase), but with a reduced activity.
HMDBP00267PGAM27p13-p12BC00190413.1.3.13; 5.4.2.11; 5.4.2.422642141361160142298999142318100814252010191021Alpha-enolaseP06733Multifunctional enzyme that, as well as its role in glycolysis, plays a part in various processes such as growth control, hypoxia tolerance and allergic responses. May also function in the intravascular and pericellular fibrinolytic system due to its ability to serve as a receptor and activator of plasminogen on the cell surface of several cell-types such as leukocytes and neurons. Stimulates immunoglobulin production.
MBP1 binds to the myc promoter and acts as a transcriptional repressor. May be a tumor suppressor.
HMDBP01087ENO11p36.2AL83374114.2.1.112266259621471413621601418242614229999914231910081425211019712Pyruvate kinase isozymes R/LP30613Plays a key role in glycolysis (By similarity).
HMDBP00765PKLR1q21S6071212.7.1.40171982267259661471413631601418682614232010085479Mitochondrial pyruvate carrier 1Q9Y5U8Mediates the uptake of pyruvate into mitochondria.
HMDBP11834MPC16q27AF151887184401719Pyruvate carboxylase, mitochondrialP11498Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
HMDBP00019PC11q13.4-q13.5K0228216.4.1.1284168982395323982136975702142225958142226171425351020142606120143727116644Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialP08559The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
HMDBP00046PDHA1Xp22.1M2915511.2.4.120641780363911136962702141132614212354142522102014259312012Pyruvate dehydrogenase E1 component subunit beta, mitochondrialP11177The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
HMDBP00012PDHB3p21.1-p14.2M3447911.2.4.12074172736392113696370214212454142523102014259412053Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialP10515The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
HMDBP00055DLAT11q23.1AP00090712.3.1.122144178786393113696470214212554142524102014259512052Dihydrolipoyl dehydrogenase, mitochondrialP09622Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
HMDBP00054DLD7q31-q32L1375711.8.1.4217410803467086394113696570214212654142525102014259612041Citrate synthase, mitochondrialO75390HMDBP00043CS12q13.2AF04704212.3.3.122041316643136966702139926802142127541425261020142597120836L-lactate dehydrogenase A-like 6AQ6ZMR3Displays an lactate dehydrogenase activity. Significantly increases the transcriptional activity of JUN, when overexpressed.
HMDBP00893LDHAL6A11p15.1AY58131311.1.1.277208240021423349991045Monocarboxylate transporter 1P53985Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetateHMDBP01111SLC16A11p12L3180118523141423361000688Aconitate hydratase, mitochondrialQ99798Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
HMDBP00725ACO222q13.2U8793214.2.1.3223447393136980704142128541425401023142611119842Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrialP50213HMDBP00899IDH3A15q25.1-q25.2CH47113611.1.1.4122841369677021425271020142598120840Isocitrate dehydrogenase [NAD] subunit beta, mitochondrialO43837HMDBP00897IDH3B20p13BC00196011.1.1.4122941369687021425281020142599120843Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrialP51553HMDBP00900IDH3GXq28BC00190211.1.1.41230413696970214252910201426001204302-oxoglutarate dehydrogenase, mitochondrialQ02218
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
HMDBP00439OGDH7p14-p13BC01461711.2.4.2234410763466881369707021425301020142601120882Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrialP36957
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of 3 enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
HMDBP00939DLST14q24.3AC00653012.3.1.61235410793466981369717021425311020142602120832Succinyl-CoA ligase [ADP/GDP-forming] subunit alpha, mitochondrialP53597Catalyzes the ATP- or GTP-dependent ligation of succinate and CoA to form succinyl-CoA. The nature of the beta subunit determines the nucleotide specificity (By similarity).
HMDBP00889SUCLG12p11.2Z6820416.2.1.4; 6.2.1.524141369727021425321020142603120834Succinyl-CoA ligase [GDP-forming] subunit beta, mitochondrialQ96I99Catalyzes the GTP-dependent ligation of succinate and CoA to form succinyl-CoA (By similarity).
HMDBP00891SUCLG23p14.1AC11440116.2.1.424241369737021425331020142604120145Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrialP31040Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
HMDBP00150SDHA5p15AK29131111.3.5.12571750574136976703140491114169955142536102114260712114376711691437711173188Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrialP21912Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
HMDBP00193SDHB1p36.1-p35U1724811.3.5.12581750584136977703140492114170055142537102114260812114376811691437721173116Succinate dehydrogenase cytochrome b560 subunit, mitochondrialQ99643Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
HMDBP00121SDHC1q23.3AK29430512591750594136978703140493114170155142538102114260912114376911691437731173174Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrialO14521Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q) (By similarity).
HMDBP00179SDHD11q23BC02235012601750604136979703140494114170255142539102114261012114377011691437741173806Fumarate hydratase, mitochondrialP07954Also acts as a tumor suppressor.
HMDBP00861FH1q42.1U5930914.2.1.226341369747021425341020142605120805Malate dehydrogenase, cytoplasmicP40925HMDBP00860MDH12p13.3AK31233111.1.1.37; 1.1.1.961722823902506141418302614183254658Glutamate dehydrogenase 1, mitochondrialP00367
Mitochondrial glutamate dehydrogenase that converts L-glutamate into alpha-ketoglutarate. Plays a key role in glutamine anaplerosis by producing alpha-ketoglutarate, an important intermediate in the tricarboxylic acid cycle. May be involved in learning and memory reactions by increasing the turnover of the excitatory neurotransmitter glutamate (By similarity).
HMDBP00694GLUD110q23.3X6630611.4.1.3144414705448753639Glutaminase liver isoform, mitochondrialQ9UI32Plays an important role in the regulation of glutamine catabolism. Promotes mitochondrial respiration and increases ATP generation in cells by catalyzing the synthesis of glutamate and alpha-ketoglutarate. Increases cellular anti-oxidant function via NADH and glutathione production. May play a role in preventing tumor proliferation.
HMDBP00675GLS212q13CH47105413.5.1.21378445441323143913541700Neutral amino acid transporter B(0)Q15758Has a broad substrate specificity, a preference for zwitterionic amino acids, and a sodium-dependence. It accepts as substrates all neutral amino acids, including glutamine, asparagine, and branched-chain and aromatic amino acids, and excludes methylated amino acids, anionic amino acids, and cationic amino acids. Act as a cell surface receptor for feline endogenous virus RD114, baboon M7 endogenous virus and type D simian retrovirusesHMDBP01955SLC1A519q13.3GQ91905811420847514316314747TransaldolaseP37837Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
HMDBP00802TALDO111p15.5-p15.4L1943712.2.1.2178621423079991430611008750TransketolaseP29401Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
HMDBP00805TKT3p14.3BC00861512.2.1.11783214230599914306010081494Ribose-5-phosphate isomeraseP49247HMDBP01611RPIA2p11.2BC01552915.3.1.61759214230699914305810083216-phosphogluconolactonaseO95336Hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate.
HMDBP00327PGLS19p13.2AJ24397213.1.1.31174021423039991430471008322Glucose-6-phosphate 1-dehydrogenaseP11413Produces pentose sugars for nucleic acid synthesis and main producer of NADPH reducing power.
HMDBP00328G6PDXq28M6522811.1.1.491730214230299914304610081431111669766-phosphogluconate dehydrogenase, decarboxylatingP52209Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH (By similarity).
HMDBP01039PGD1p36.22AL13942411.1.1.44506228759814230499914305310085711Mitochondrial citrate transport proteinQ6LAP8X969241242917689Cytoplasmic aconitate hydrataseP21399Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding.
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
HMDBP00726ACO19p21.1BC01810314.2.1.35066289598841Isocitrate dehydrogenase [NADP] cytoplasmicO75874HMDBP00898IDH12q33.3BX53741111.1.1.4250672710Pyruvate kinase PKMP14618Glycolytic enzyme that catalyzes the transfer of a phosphoryl group from phosphoenolpyruvate (PEP) to ADP, generating ATP. Stimulates POU5F1-mediated transcriptional activation. Plays a general role in caspase independent cell death of tumor cells. The ratio betwween the highly active tetrameric form and nearly inactive dimeric form determines whether glucose carbons are channeled to biosynthetic processes or used for glycolytic ATP production. The transition between the 2 forms contributes to the control of glycolysis and is important for tumor cell proliferation and survival.
HMDBP00763PKM15q22AK30080012.7.1.4050682142300999143789116914379011712356L-lactate dehydrogenase A chainP00338HMDBP03579LDHA11p15.4CR54171411.1.1.278964814050211421172614378811694308Probable 2-oxoglutarate dehydrogenase E1 component DHKTD1, mitochondrialQ96HY7
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3) (By similarity).
HMDBP09099DHTKD110p14AC07316011.2.4.2515131422304916Fructose-bisphosphate aldolase AP04075Plays a key role in glycolysis and gluconeogenesis. In addition, may also function as scaffolding protein (By similarity).
HMDBP00978ALDOA16p11.2BC01066014.1.2.131028817912595714713887829714135516014221299914231210081425141019398Solute carrier family 2, facilitated glucose transporter member 21PW_P00039842024491578Hexokinase-21PW_P0005786192071495Glucose-6-phosphate isomerase1PW_P00049551975122856-phosphofructokinase, liver type1PW_P00028530470641284231723Fructose-bisphosphate aldolase B 1PW_P000723817918291Glyceraldehyde-3-phosphate dehydrogenase1PW_P0002913106594969Phosphoglycerate kinase 11PW_P000969109514171588Phosphoglycerate mutase 21PW_P0005886322611589Alpha-enolase1PW_P000589633102112794231471Pyruvate kinase PKLR1PW_P000471494712422542312264571303Mitochondrial pyruvate carrier1PW_P000303322547911097175Pyruvate carboxylase, mitochondrial1PW_P000005619452016102748461Pyruvate dehydrogenase complex1PW_P00006168446069126070536071522434106013576913696424236457Citrate synthase, mitochondrial1PW_P000057604122187210L-lactate dehydrogenase1PW_P000210228235611130Monocarboxylate transporter1PW_P00113012921045158Aconitate hydratase, mitochondrial1PW_P000058616881460407111221459Isocitrate dehydrogenase1PW_P000059628422638401648431304234225460Oxoglutarate dehydrogenase complex1PW_P0000606543081668821675223110601327691339642232462Succinyl-CoA ligase1PW_P000062728321738341237464Succinate dehydrogenase1PW_P0000647514517618817711617817413896414234055812431766Fumarate hydratase, mitochondrial1PW_P0000668080642614473Malate dehydrogenase, cytoplasmic1PW_P000473496805132Glutamate dehydrogenase 1, mitochondrial1PW_P000032336586125436Glutaminase liver isoform, mitochondrial1PW_P00003637639113113748Neutral amino acid transporter B(0)1PW_P00074884317001492Transaldolase1PW_P0004925167472490Transketolase1PW_P0004905137502237423224510602483Ribose-5-phosphate isomerase1PW_P000483506149414776-phosphogluconolactonase1PW_P0004775003211475Glucose-6-phosphate 1-dehydrogenase1PW_P000475498322411316-phosphogluconate dehydrogenase, decarboxylating1PW_P00113112939762618Mitochondrial citrate transport protein 1PW_P00061866257112430171132Cytoplasmic aconitate hydratase1PW_P001132129468914694071111133Isocitrate dehydrogenase [NADP] cytoplasmic1PW_P0011331295841247042311134Pyruvate kinase PKM1PW_P00113412967102287Fructose-bisphosphate aldolase A1PW_P00028730691641231falsePW_R001231Right4695771Compoundfalse46964141Compoundtrue469710831Compoundfalse469810341Compoundtrue9365782.7.1.11057falsePW_R001057Both4081791Compoundfalse408210831Compoundfalse7134955.3.1.9805falsePW_R000805Right3266791Compoundfalse32674141Compoundtrue32688331Compoundfalse326910341Compoundtrue3422852.7.1.11807falsePW_R000807Both32748331Compoundfalse327511341Compoundfalse32768691Compoundfalse3442874.1.2.1313157234.1.2.13812falsePW_R000812Both32908691Compoundfalse32917211Compoundtrue329214411Compoundtrue32939831Compoundfalse329411441Compoundtrue3492911241falsePW_R001241Right47569831Compoundfalse475710341Compoundtrue47586441Compoundfalse47594141Compoundtrue9539692.7.2.31246falsePW_R001246Both47806441Compoundfalse478118701Compoundfalse958588243falsePW_R000243Both104418701Compoundfalse10451801Compoundfalse104614201Compoundtrue9605894.2.1.11365falsePW_R000365Both15134141Compoundtrue15141641Compoundfalse151510341Compoundtrue15161801Compoundfalse6594712.7.1.404falsePW_R000004Right154141Compoundtrue161641Compoundfalse174631Compoundtrue1810341Compoundtrue1911041Compoundtrue201481Compoundfalse456.4.1.1594falsePW_R000594Right25001641Compoundfalse250110991Compoundtrue25027211Compoundtrue25039401Compoundfalse250413161Compoundtrue250511441Compoundtrue69611.2.4.1590falsePW_R000590Right24769401Compoundfalse247714201Compoundtrue24781481Compoundfalse2479631Compoundfalse248010991Compoundtrue62572.3.3.1374falsePW_R000374Both15491221Compoundfalse15507211Compoundtrue15511641Compoundfalse155211441Compoundtrue1553400341Compoundtrue6582101.1.1.2788falsePW_R000088Right348631Compoundfalse3491251Compoundfalse2237584.2.1.3224111324.2.1.3332falsePW_R000332Right13801251Compoundfalse13817211Compoundtrue13821341Compoundfalse138313161Compoundtrue138411441Compoundtrue1385400341Compoundtrue70591.1.1.41592falsePW_R000592Right24871341Compoundfalse24887211Compoundtrue248910991Compoundtrue24908081Compoundfalse249111441Compoundtrue2492400341Compoundtrue249313161Compoundtrue67601.2.4.2593falsePW_R000593Both24948081Compoundfalse249511041Compoundtrue24969361Compoundtrue24971741Compoundfalse249810991Compoundtrue24999861Compoundtrue6862233falsePW_R000233Both10101741Compoundfalse10118461Compoundtrue25129641Compoundtrue1012881Compoundfalse101310061Compoundtrue25139321Compoundtrue75641.3.5.1269falsePW_R000269Both11451011Compoundfalse1146881Compoundfalse114714201Compoundtrue78664.2.1.2390falsePW_R000390Both16051011Compoundfalse16067211Compoundtrue16071481Compoundfalse160811441Compoundtrue1609400341Compoundtrue7947338falsePW_R000038Right136951Compoundfalse13714201Compoundtrue1387211Compoundtrue1391341Compoundfalse140351Compoundtrue14111441Compoundtrue38321.4.1.343falsePW_R000043Right1625001Compoundfalse16314201Compoundtrue164951Compoundfalse165351Compoundtrue43363.5.1.21047falsePW_R001047Both404110191Compoundfalse4042791Compoundfalse40438691Compoundfalse40448431Compoundfalse7024922.2.1.21045falsePW_R001045Both40328691Compoundfalse40338431Compoundfalse403411911Compoundfalse40356911Compoundfalse7004902.2.1.11041falsePW_R001041Both40204791Compoundfalse402111911Compoundfalse6924835.3.1.674falsePW_R000074Right2858811Compoundfalse28614201Compoundtrue28710151Compoundfalse903410511Compoundtrue22394773.1.1.311058falsePW_R001058Both408319061Compoundfalse408410831Compoundfalse7144955.3.1.92337falsePW_R002337Both903519061Compoundfalse90361431Compoundtrue90378811Compoundfalse90381461Compoundtrue9039400341Compoundtrue22404751.1.1.491030falsePW_R001030Right399210151Compoundfalse90401431Compoundtrue39934791Compoundfalse399413161Compoundtrue90411461Compoundtrue67811311.1.1.442338falsePW_R002338Right90421251Compoundfalse90431431Compoundtrue90441341Compoundfalse90451461Compoundtrue904613161Compoundtrue224211331.1.1.42279PW_T000279318771Compound152Both2273982014-03-19T21:44:31-06:002014-03-19T21:44:31-06:00141PW_T00000111641Compound24Right63032013-07-08T16:38:23-06:002013-07-08T16:38:23-06:0017280PW_T0002803191221Compound215Right22811302014-03-20T00:32:24-06:002014-03-20T00:32:24-06:0014281PW_T0002813205001Compound24Right139PW_T0001391615001Compound158Right1017482013-09-05T02:17:20-06:002013-09-05T02:17:20-06:001472PW_T00007282631Compound24Left366182013-08-16T13:09:33-06:002013-08-16T13:09:33-06:001711616771581false164032510regular2001901161777281false164079010regular20019011618414242false1820101510regular5030116191083281false1640124010regular200190116201034243false1820117510regular50301162179281false1640164010regular20019011622414242false1625186010regular503011623833281false1640209010regular200190116241034243false1625202010regular50301162542329false1755191510regular10025116281134281true1450246010regular20019011629869281false1640251010regular20019011630721259false1831271510regular5030116311441246true1379253810regular444311632983281false1642293510regular200190116331144260false1832287510regular5030116341034243false1827314010regular503011635644281false1642336010regular20019011636414242false1827330010regular5030116371870281false1642378010regular20019011638180281false1642420510regular200190116391420249false1797411510regular78781164042329false1752407510regular1002511641414242false2122420010regular503011642164281false2237420510regular200190116431034243false1897420010regular50301164442329false2042432510regular100251164545729false1922432510regular1002511646164481false2897420510regular20019011647414442false2862383210regular503011648463447false2753388810regular7878116491034443false3082383210regular5030116501104446false3110399510regular444311651148481false3247383110regular200190116522049false2892394710regular1002511653102749false3007395210regular10025116541099485false3152436510regular503011655721459false3152419510regular503011656940481false3527420310regular200190116571316452false3383435910regular7878116581144460false3387419610regular503011659106049false3227421010regular100351166076949false3182433010regular100251166196449false3302433010regular10025116621420449false3732436310regular78781166363481false4032420310regular200190116641099485false3967419810regular503011665122281false2239505019regular20019011666721259false2214457010regular5030116671144260false2215442510regular50301166840034255true1933417610regular7878116691221581false2239573510regular20019011670125481false4517420310regular200190116714071149false4297432310regular1002511672721459false4767419810regular503011673134481false5162420410regular200190116741316452false5053437510regular7878116751144460false5047419710regular50301167640034455true4703424810regular78781167742349false4887435810regular1002511678721459false5137401410regular5030116791099485false5357401910regular503011680808481false5163338910regular200190116811144460false5138375410regular50301168240034455true4819358510regular7878116831316452false5327372510regular787811684106049false5134394110regular100351168576949false5294384110regular100251168696449false5124384610regular10025116871104446false4986358410regular444311688936453false4983336510regular503011689174481false4508338810regular200190116901099485false4753358810regular503011691986454false4763336810regular5030116928464139false4323336310regular5030116939644137false4423332810regular50301169488481false3803338810regular20019011695400984140false4098336810regular5030116969324138false4008331810regular50301169796449true3638333810regular10025116984055849true3778332810regular1002511699101481false3248338810regular200190117001420449false3713334810regular787811701721459false3198360310regular5030117021144460false3179378110regular50301170340034455true3120375210regular78781170495481false5161474910regular200190117051420449false5291459410regular787811706721459true4606442410regular50301170735463false5290442510regular7878117081144460true4572420410regular503011709500481false4391474810regular200190117101420449false4811471810regular78781171135463false5027472710regular787811714500881false4391517310regular200190117175001581false4391574810regular200190117181019281false2130188510regular20019011719843281false2115228010regular200190117201191281false2830251010regular20019011721691281false2540228010regular2001901172242329false2315263010regular1002511723106029false2435263010regular1003511724479281false2830214010regular200190117251015281false2829170010regular20019011727881281false2828124010regular200190117281420249false3013143510regular7878117291051255true3512202110regular7878117301906281false2165124010regular20019011731143261false2430120010regular503011732146262false2663120210regular50301173340034255false2659143310regular787811734143261false3009189510regular5030117351316252false2743206110regular787811736146262false3010210010regular50301173763281false4037517310regular20019011738125281false3452517310regular200190117394071129false3757528810regular1002511745143261false3347532810regular503011746134281false2732517110regular20019011747146262false3087533110regular5030117481316252false2998533710regular78781174942329false3197522310regular100256164244922876false16656158subunitregular15070616520722false166510778subunitregular15070616675126false166014958subunitregular16080616770626false166019158subunitregular16080616991828false167023508subunitregular14085617065928false167127708subunitregular140856171141722false166732008subunitregular15070617226126false166236378subunitregular160806173102126false166240208subunitregular16080617471228false196242608subunitregular14085617554791776false260242658subunitregular1507061761948false292738878subunitregular140856177444136false321242208proteinregular17515561781242true276240858subunitregular1507061795342true275741758subunitregular1507061805242true278242658subunitregular1507061814142false381242638subunitregular15070618283628false226944758subunitregular14085618310451476false226454308subunitregular15070618468842false427242638subunitregular15070618584246false484742288subunitregular160806186840497false480242988subunitregular150706187843498false491742988subunitregular1507061884304136false517438218proteinregular175155618988242true467937528subunitregular1507061905242true467937518subunitregular150706191832497false480834868noneregular15070619283442false481334218proteinregular150706193145499false414834088noneregular150706194188498false417334288noneregular150706195116497false414334338noneregular15070619617442false415834488proteinregular15070619780648false356334438subunitregular14085619880542false327336798subunitregular150706199658417false517145048subunitregular18085620063942false488648088subunitregular150706203170076false441654338subunitregular15070620474726false193521008subunitregular16080620575026false234525658subunitregular160806206149422false285523908subunitregular15070620832122false285315508subunitregular15070620975122false193013008subunitregular15070621032228false249912958subunitregular14085621197626false284919778subunitregular160806212571176false406249388subunitregular15070621368922false373252338subunitregular15070621584126false316752288subunitregular1608062167102113false195238908subunitregular1608050213983786062616450225783782606361655023495378260646166502428537826065616723721162518125Cofactor5026723378260676169502729137826068617050289693782606961715029588378260706172503058937826071617323731164018146Cofactor503147137826072617423741164418151Cofactor23751164518152Cofactor5032303378607361755033537846074617623761165218161Cofactor23771165318162Cofactor50346137846075617760766178607761796078618023781165918169Cofactor23791166018170Cofactor23801166118171Cofactor5035573784607961815036210378260806182503711303786081618350385837846082618423811167118186Cofactor503959378460836185608461866085618723821167718193Cofactor504060378460866188608761896088619023831168418201Cofactor23841168518202Cofactor23851168618203Cofactor5041623784608961916090619250426437846091619360926194609361956094619623861169718216Cofactor23871169818217Cofactor50436637846095619750444733784609661985045323784609761995046363784609862005049748378610162035050492378261026204505149037826103620523881172218252Cofactor23891172318253Cofactor5052483378261046206505447737826106620850554953782610762095056475378261086210505711313782610962115058618378611062125059113237826111621323901173918279Cofactor5061113337826113621523921174918291Cofactor5062113437826114621618113M1740 515 C1740 545 1740 585 1740 615 83false1818114M1740 790 C1740 760 1740 715 1740 685 83false18trueM 87.5 347.0096189432334 L 95 360 L 102.5 347.0096189432334false18115M1740 980 C1740 1010 1740 1047.5 1740 1077.5 5false1818116M1820 1030 C1785 1030 1740 1047 1740 1077 5false1818117M1740 1240 C1740 1210 1740 1177 1740 1147 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18118M1820 1190 C1792 1190 1740 1177 1740 1147 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18119M1740 1640 C1740 1610 1740 1605 1740 1575 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18120M1740 1430 C1740 1460 1740 1465 1740 1495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18121M1740 1830 C1740 1860 1740 1885 1740 1915 5false1818122M1675 1875 C1705 1875 1740 1885 1740 1915 5false1818123M1740 2090 C1740 2060 1740 2025 1740 1995 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18124M1675 2035 C1702 2035 1740 2025 1740 1995 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18125M1545 1965 L1545 2015 L1595 1965 z10true1818129M1740 2280 C1740 2310 1740 2320 1740 2350 5false18falsefalse18130M1550 2460 C1550 2430 1740 2465 1740 2435 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18131M1740 2510 C1740 2480 1740 2465 1740 2435 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18132M1740 2700 C1740 2730 1741 2740 1741 2770 5false18falsefalse18133M1831 2730 C1800 2730 1741 2740 1741 2770 5false18falsefalse18134M1401 2581.5 C1401 2611.5 1741 2740 1741 2770 5true18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18135M1742 2935 C1742 2905 1741 2885 1741 2855 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18136M1832 2890 C1808 2890 1741 2885 1741 2855 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18137M1742 3125 C1742 3155 1742 3170 1742 3200 5false1818138M1827 3155 C1792 3155 1742 3170 1742 3200 5false1818139M1742 3360 C1742 3330 1742 3300 1742 3270 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18140M1827 3315 C1798 3315 1742 3300 1742 3270 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18141M1742 3550 C1742 3580 1742 3607 1742 3637 5false18falsefalse18142M1742 3780 C1742 3750 1742 3747 1742 3717 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18143M1742 3970 C1742 4000 1742 3990 1742 4020 5false18falsefalse18144M1742 4205 C1742 4175 1742 4130 1742 4100 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18145M1797 4154 C1764 4154 1742 4130 1742 4100 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18146M1657 4000 L1657 4050 L1707 4000 z10true1818147M2147 4230 C2147 4258 2132 4300 2102 4300 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18148M2237 4300 C2207 4300 2132 4300 2102 4300 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18149M1922 4230 C1922 4258 1932 4300 1962 4300 5false18falsefalse18150M1842 4300 C1872 4300 1932 4300 1962 4300 5false18falsefalse18151M1732 4120 L1732 4170 L1782 4120 z10true1818152M1732 4120 L1732 4170 L1782 4120 z10true1818153M2437 4300 C2467 4300 2572 4300 2602 4300 83false18falsefalse18154M2897 4300 C2867 4300 2782 4300 2752 4300 83false18falsefalse18155M2887 3862 C2885 3892 2897 3927 2927 3927 5false1818156M2997 4205 C2997 4150 2998 4075 2997 3972 5false1818157M2831 3927 C2865 3927 2897 3927 2927 3927 5false1818158M3107 3862 C3105 3891 3097 3927 3067 3927 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18159M3132 3995 C3132 3963 3115 3927 3067 3927 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18160M3247 3926 C3192 3926 3127 3927 3067 3927 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18161M2907 4132 L2907 4182 L2957 4132 z10true1818162M2907 4132 L2907 4182 L2957 4132 z10true1818163M3097 4300 C3144 4300 3143 4300 3217 4300 5false1818164M3177 4365 C3177 4332 3187 4300 3217 4300 5false1818165M3177 4225 C3177 4256 3187 4300 3217 4300 5false1818166M3527 4298 C3497 4298 3417 4300 3387 4300 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18167M3422 4359 C3422 4325 3417 4300 3387 4300 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18168M3412 4226 C3412 4259 3417 4300 3387 4300 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18169M2907 4180 L2907 4230 L2957 4180 z10true1818170M2907 4180 L2907 4230 L2957 4180 z10true1818171M2907 4180 L2907 4230 L2957 4180 z10true1818172M3727 4298 C3782 4298 3752 4298 3812 4298 5false1818173M3771 4363 C3771 4324 3782 4298 3812 4298 5false1818174M3347 4021 C3347 4070 3345 4062 3346 4132 C3464 4129 3638 4129 3721 4129 C3733 4167 3742 4279 3812 4298 5false1818175M4032 4298 C4002 4298 3992 4298 3962 4298 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false18176M3992 4228 C3992 4275 3992 4298 3962 4298 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 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3212 C4049 3212 4076 3293 4076 3337 C4076 3507 4343 3512 4343 3342 C4343 3291 4363 3215 4443 3215 C4602 3215 5205 3224 5371 3224 C5494 3224 5465 3344 5465 3427 C5465 3729 5460 4085 5460 4376 C5473 5020 5474 4974 5026 4973 C4481 4973 3426 4972 2871 4972 C2719 4971 2719 4972 2722 4333 C2722 4043 2722 3644 2722 3357 C2722 3285 2817 3212 2892 3212 C3203 3212 3670 3212 3946 3212 84false62743.01761.0721M2625 3232 C2625 3182 2675 3132 2725 3132 C3557 3132 4640 3132 5472 3132 C5522 3132 5572 3182 5572 3232 C5572 3758 5572 4443 5572 4969 C5572 5019 5522 5069 5472 5069 C4640 5069 3557 5069 2725 5069 C2675 5069 2625 5019 2625 4969 C2625 4443 2625 3758 2625 3232 84true62947.01937.0722M1104 758 C1104 708 1154 658 1204 658 C2540 658 4277 658 5613 658 C5663 658 5713 708 5713 758 C5713 2156 5713 3972 5713 5370 C5713 5420 5663 5470 5613 5470 C4277 5470 2540 5470 1204 5470 C1154 5470 1104 5420 1104 5370 C1104 3972 1104 2156 1104 758 1true64609.04812.094615Lactate shuttle20105420201.31.31601594715 Pentose Phosphate Shunt 21201525203.43.41601594815Citric Acid Cycle40753735203.73.71601594915Inner Mitochondrial Membrane30603170201.01.01601595015Outer Mitochondrial Membrane30553090201.01.016015951235Mitochondrion45752520202.22.220015952235Cytosol3090650202.52.52001595315Glycolysis8201830203.43.416015193715Phosphoenolpyruvic acid12744223201.91.916015193815Pyruvic acid21784068201.91.916015193915L-Lactic acid21685226201.91.9160151940152-Phospho-D-glyceric acid13003804201.91.9160151941153-Phosphoglyceric acid12953391201.91.916015194215Glyceric acid 1,3-biphosphate12952944201.91.916015194315D-Glyceraldehyde 3-phosphate13052529201.91.916015194415Fructose 6-phosphate12521634202.22.216015194515Fructose 1,6-bisphosphate12922133201.91.916015200715Pyruvate kinase PKLR18604336201.91.916015200815L-lactate dehydrogenase21814502201.91.916015200915Pyruvate kinase PKM18713769201.91.91601589055815The production of ATP through the Citric Acid Cycle is limited to 1%.24584330201.91.91601589055915Lactic acid accumulation leads to a low pH microenvironment17365045202.22.21601589056115The large lactate efflux leads to activation of many factors in adjacent cells involved in angiogenesis.17775719202.22.21601589056215Low conversion of PEP into pyruvate can lead to the accumulation of upstream glycolytic intermediates. Intermediates are used for synthesis of nucleotides, amino acids and fatty acids required in proliferation. 17984594202.22.216015890601235Angiogenesis28696109202.52.520015890602235Proliferation1795193202.52.520015890604235Cancer Cell400520202.22.220015890605235Nucleus35161462202.52.5200154654392255825563056563551304#FFEBEB4307920742824688803091043592578655394447434947