2176PathwaySerine MetabolismThe biosynthesis of serine begins with 3-phospho-D-glycerate being metabolize into 3-phosphohydroxypyruvate through a 3-phosphoglycerate dehydrogenase. The resulting compound 3-phosphohydroxypyruvate is transaminated into 3-phospho-L-serine through a phosphoserine transaminase. This is followed by 3-phospho-L-serine being dephosphorylated through a phosphoserine phosphatase resulting in the release of a phosphate and Serine.
Serine can also be incorporated into the mitochondrion and then serine can then be used to synthesize glycine through a mitochondrial serine hydroxymethyltransferase. Glycine is then used to synthesize formic acid by first being metabolized into 5,10 methylene THF, which is transformed into a 5,10 methenyltetrahydrofolate , followed by an N10 formyl tetrahydrofolate and lastly formic acid, all through a mitochondrial C1-tetrahydrofolate synthase.
In the cytosol serine can either be degraded to synthesize glycine through a serine hydroxymethyltransferase or it can be degraded into 2-aminoprop-2-enoate. The latter compound can be spontaneously be converted first into 2-iminopropanoate and this compound is then converted into pyruvic acid.
MetabolicPW002402CenterPathwayVisualizationContext268825013051#000099PathwayVisualization21592176Serine MetabolismThe biosynthesis of serine begins with 3-phospho-D-glycerate being metabolize into 3-phosphohydroxypyruvate through a 3-phosphoglycerate dehydrogenase. The resulting compound 3-phosphohydroxypyruvate is transaminated into 3-phospho-L-serine through a phosphoserine transaminase. This is followed by 3-phospho-L-serine being dephosphorylated through a phosphoserine phosphatase resulting in the release of a phosphate and Serine.
Serine can also be incorporated into the mitochondrion and then serine can then be used to synthesize glycine through a mitochondrial serine hydroxymethyltransferase. Glycine is then used to synthesize formic acid by first being metabolized into 5,10 methylene THF, which is transformed into a 5,10 methenyltetrahydrofolate , followed by an N10 formyl tetrahydrofolate and lastly formic acid, all through a mitochondrial C1-tetrahydrofolate synthase.
In the cytosol serine can either be degraded to synthesize glycine through a serine hydroxymethyltransferase or it can be degraded into 2-aminoprop-2-enoate. The latter compound can be spontaneously be converted first into 2-iminopropanoate and this compound is then converted into pyruvic acid.
Metabolic18112353EndocytosisSubPathway50201628804Bornaes C, Petersen JG, Holmberg S: Serine and threonine catabolism in Saccharomyces cerevisiae: the CHA1 polypeptide is homologous with other serine and threonine dehydratases. Genetics. 1992 Jul;131(3):531-9.2176Pathway502112525494Albers E, Laize V, Blomberg A, Hohmann S, Gustafsson L: Ser3p (Yer081wp) and Ser33p (Yil074cp) are phosphoglycerate dehydrogenases in Saccharomyces cerevisiae. J Biol Chem. 2003 Mar 21;278(12):10264-72. doi: 10.1074/jbc.M211692200. Epub 2003 Jan 13.2176Pathway5022Jones EW and Fink GRĀ Regulation of amino acid and nucleotide biosynthesis in yeast. in The Molecular Biology of the Yeast Saccharomyces: Metabolism and Gene Expression, edited by Strathern JN, Jones EW and Broach JR. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press (1982) p.181-2992176Pathway1CellCL:00000005HepatocyteCL:00001826MyocyteCL:00001873NeuronCL:00005404Cardiomyocyte CL:00007467Epithelial CellCL:000006610Glial cellCL:00001252Platelet CL:00002338Beta cellCL:00006391Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato4Arabidopsis thaliana3702EukaryoteThale cress18Saccharomyces cerevisiae4932EukaryoteYeast23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly6Caenorhabditis elegans6239EukaryoteRoundworm2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote21Xenopus laevis8355EukaryoteAfrican clawed frog60Nitzschia sp.0001EukaryoteNitzschia425Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast5CytoplasmGO:00057371CytosolGO:000582935ChloroplastGO:00095073Mitochondrial MatrixGO:00057592MitochondrionGO:00057397Endoplasmic Reticulum MembraneGO:000578925Golgi apparatusGO:00057944PeroxisomeGO:000577712Mitochondrial Inner MembraneGO:00057436LysosomeGO:000576413Endoplasmic ReticulumGO:000578316Lysosomal LumenGO:004320211Extracellular SpaceGO:000561514Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575831Periplasmic SpaceGO:000562010Cell MembraneGO:000588636MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032532Inner MembraneGO:007025818Melanosome MembraneGO:003316220Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520215NucleusGO:000563440PeriplasmGO:004259719sarcoplasmic reticulumGO:001652927Peroxisome MembraneGO:00057781LiverBTO:000075972928StomachBTO:0001307155268Blood VesselBTO:000110274119MuscleBTO:00008871411824BrainBTO:000014289164Adrenal MedullaBTO:000004971825IntestineBTO:00006487Nervous SystemBTO:000148411HeartBTO:000056273105cardiocyteBTO:00015392Endothelium BTO:000039318PancreasBTO:00009888511PW_BS0000082111PW_BS000002117131PW_BS0001171471241PW_BS000147151141PW_BS0001511601181PW_BS0001602253541PW_BS0000243221231PW_BS0000241321121PW_BS0001321115121PW_BS000111124151PW_BS000124122551PW_BS0001221181171PW_BS0001181355171PW_BS0001352991101PW_BS000024388161PW_BS0001124311PW_BS0000043211PW_BS000003101711PW_BS000010432511PW_BS0000435411PW_BS000005541315PW_BS00005449711PW_BS000049171211PW_BS00001729111PW_BS0000299611PW_BS000009181311PW_BS0000182811611PW_BS0000286131PW_BS000006311511PW_BS000031951721PW_BS000095103331PW_BS0001031122121PW_BS0001121231751PW_BS0001231251351PW_BS000125100521PW_BS00010010813PW_BS00010814117191PW_BS0001411553241PW_BS0001551572241PW_BS0001571613181PW_BS00016111PW_BS0000011783211PW_BS000178188118PW_BS0000241632181PW_BS000163205561PW_BS000024206261PW_BS0000241985181PW_BS000024222341PW_BS000024226441PW_BS000024224241PW_BS0000242164181PW_BS0000242491341PW_BS00002429817101PW_BS00002430013101PW_BS0000242231241PW_BS000024315123PW_BS0000241333121PW_BS00013313412121PW_BS0001343317121PW_BS0000283361121PW_BS0000283344121PW_BS00002833217121PW_BS00002813013121PW_BS0001301136121PW_BS00011334713125PW_BS00002835625121PW_BS0000283683601PW_BS0000281192171PW_BS00011916611PW_BS000166943PW_BS000094406351PW_BS000115407251PW_BS0001154192551PW_BS000115408451PW_BS0001154251355PW_BS000115126651PW_BS000126429151PW_BS000115383751PW_BS0001003841251PW_BS0001001203171PW_BS00012044717171PW_BS00011513613171PW_BS00013645525171PW_BS0001153744171PW_BS00005346013175PW_BS0001154436171PW_BS0001154641171PW_BS0001153987171PW_BS00011312112171PW_BS0001212975101PW_BS0000244793101PW_BS0001154812101PW_BS00011549025101PW_BS0001154824101PW_BS0001154957101PW_BS00011548012101PW_BS000115501361PW_BS0001155072561PW_BS000115502461PW_BS000115390761PW_BS0001123911261PW_BS0001123951361PW_BS00011315111PW_BS000015261115PW_BS000026221411PW_BS000022422411PW_BS0000427028511PW_BS000070107313PW_BS000107105113PW_BS00010515924PW_BS00015915284PW_BS000152101531PW_BS0001011873118PW_BS000024219314PW_BS00002422014PW_BS0000242137181PW_BS00002421013181PW_BS00002421217181PW_BS00002417018PW_BS00017016212181PW_BS0001621951318PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS0000242941141PW_BS0000243081011PW_BS0000243183123PW_BS0000243125231PW_BS0000243201123PW_BS00002429341PW_BS0000241141112PW_BS00011432711125PW_BS00002834524121PW_BS000028310312PW_BS00002430412PW_BS000024109323PW_BS000109409115PW_BS0001154241155PW_BS0001154182451PW_BS0001151371117PW_BS00013745911175PW_BS00011545424171PW_BS0001154831110PW_BS00011548924101PW_BS000115208116PW_BS0000245062461PW_BS00011514101PW_BS000014509516PW_BS00005085241011PW_BS00008572513PW_BS000072711113PW_BS000071207661PW_BS0000242892491PW_BS0000242905491PW_BS000024253541PW_BS00002434695126PW_BS0000284239556PW_BS00011545895176PW_BS0001153016101PW_BS00002412915121PW_BS0001294141551PW_BS00011545015171PW_BS00011513121PW_BS000013204111PW_BS000020331811PW_BS0000332441011PW_BS00002460251PW_BS00006046114PW_BS000046612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097110231PW_BS00011012711651PW_BS000127140103PW_BS00014014315191PW_BS0001431465191PW_BS0001461802211PW_BS0001802111018PW_BS00002421425181PW_BS0000242156181PW_BS0000241901118PW_BS0000242771218PW_BS00002465111PW_BS0000652916491PW_BS0000242924491PW_BS000024302116101PW_BS0000243331212PW_BS0000281151012PW_BS000115337116121PW_BS00002834141121PW_BS00002834318121PW_BS00002832914121PW_BS0000283522512PW_BS00002835325127PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS000115405105PW_BS0001154151851PW_BS00011543441051PW_BS0001153821451PW_BS000100436255PW_BS0001154461217PW_BS0001153761017PW_BS000053448116171PW_BS00011545118171PW_BS000115469410171PW_BS00011539914171PW_BS0001134712517PW_BS00011547225177PW_BS0001154781010PW_BS00011548718101PW_BS00011548414101PW_BS000115209106PW_BS0000245041861PW_BS00011551541061PW_BS0001153891461PW_BS0001125131761PW_BS000115471914PW_BS000047231511PW_BS000023241529PW_BS00002425715291PW_BS00002420175110PW_BS000024202711110PW_BS0000243511512PW_BS000028435155PW_BS0001154701517PW_BS0001154991510PW_BS000115517156PW_BS0001153551914PW_BS0000355811411PW_BS000058592711PW_BS000059918511PW_BS0000912171518PW_BS00002421815181PW_BS00002431323PW_BS000024350114121PW_BS00002812815121PW_BS00012833527121PW_BS00002843311451PW_BS0001154101551PW_BS0001154222751PW_BS000115468114171PW_BS00011544415171PW_BS00011537527171PW_BS00005348515101PW_BS00011549127101PW_BS0001155161561PW_BS0001155082761PW_BS00011516212PW_BS0000163211515PW_BS000032397113PW_BS0000396618518PW_BS0000665181PW_BS000051892PW_BS0000891041431PW_BS00010419914181PW_BS000024184121PW_BS00002415612241PW_BS0001561771211PW_BS0001773671601PW_BS000028243229PW_BS0000246443-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_C000644G3P205182257257431175917147594815168971608358225426233227711113278033111121192124121386122123763118123945135125960299127417388721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium664.433664.116946663-2.5981-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-1FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;Ī²-nadPW_C000721NAD140415033538651101114211344312735146654222949277917283529310794807184813184819284902649603151679552381035334111536011254691235482125559013556101185696100573810858271415912147594215160241556072157607616163851646917867721176890160701218870971637174205719720674051987459222824122683592259085224118192161232224913006298130183001325622342404322426193157710413277120133772091347737033177650336776673347770233277709130779151137798334778406356800063688069011993825124110552388112750166112853941199291221199524061201714071208344191209844081211594251212421261212594291218173831226143841227421201231304471231411361234194551235493741237314601238124431238294641243703981251871211253192971253424791255304811258062991258254901259244821265154951267654801268855011272785071273835021280893901283603911284283951144NADHHMDB0001487NADH 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_C001144NADH1434153349086481011152127551469542230492781172836293109948061848121848212849046495931516995524010353321115358112546612354791255593135569810057371085829141591514759451516027155607916163871647217867711176893160701118870991637172205719520674622228244226836022590862241180919811821216123202491300329813015300132552234240332242618315771071327712313377208134773713317765133677668334777003327770713077917113779863478000936880691119938221241105493881128549411583811811995540612017240712037812212098640812116242512124412612169342912181838312261638412274512012312744712313813612355137412373446012381444312424246412437139812518912112534547912553148112576229712580829912592648212651649512676748012688850112738550212809039012836239112842939540034Hydrogen 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+215467087531578831848311162146326146454223149278017425022425442454710457618469470524110353271115353112562610856391075699100572010557421175963147603715560701576093161613015962321666483178660115266921016843188691018771001637168205719120674532197454220747222275252137532210755821275721607590170819522582181518243226841316284202249139195915524911915164120152811218128512246286122662871252122713257223133252941533030842329315423543184240132242405312424543207691229377136133772101347737233177804114779551327799032777991347783793457992913080019368803873108038830480722119938231249482338311055038811285594113280390115537398115539118115856336116205109119973406120193407120549122120593409121170424121171425122569418122615384122687125122758120123183135123218137123742459123743460125141454125188121125273136125359479125550481125730483125736297125809299126517495126717489126766480126823300126902501127213208128308506128361391128430395810Phosphohydroxypyruvic acidHMDB0001024Phosphohydroxypyruvic acid, also known as 3-phosphonooxypyruvate or hydroxypyruvic acid phosphate, belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position. Phosphohydroxypyruvic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, phosphohydroxypyruvic acid is primarily located in the cytoplasm. Phosphohydroxypyruvic acid exists in all living organisms, ranging from bacteria to humans. Phosphohydroxypyruvic acid participates in a number of enzymatic reactions. In particular, Phosphohydroxypyruvic acid can be biosynthesized from 3-phosphoglyceric acid; which is mediated by the enzyme D-3-phosphoglycerate dehydrogenase / Ī±-ketoglutarate reductase. Furthermore, Phosphohydroxypyruvic acid and L-glutamic acid can be converted into oxoglutaric acid and DL-O-phosphoserine; which is mediated by the enzyme 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase. Furthermore, Phosphohydroxypyruvic acid can be biosynthesized from 3-phosphoglyceric acid through its interaction with the enzyme D-3-phosphoglycerate dehydrogenase / Ī±-ketoglutarate reductase. Furthermore, Phosphohydroxypyruvic acid and L-glutamic acid can be converted into oxoglutaric acid and DL-O-phosphoserine; which is catalyzed by the enzyme 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase. Furthermore, Phosphohydroxypyruvic acid can be biosynthesized from 3-phosphoglyceric acid through its interaction with the enzyme D-3-phosphoglycerate dehydrogenase / Ī±-ketoglutarate reductase. Finally, Phosphohydroxypyruvic acid and L-glutamic acid can be converted into oxoglutaric acid and DL-O-phosphoserine through its interaction with the enzyme 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase. In humans, phosphohydroxypyruvic acid is involved in the glycine and serine metabolism pathway. Phosphohydroxypyruvic acid is also involved in several metabolic disorders, some of which include the sarcosinemia pathway, the hyperglycinemia, non-ketotic pathway, dihydropyrimidine dehydrogenase deficiency (DHPD), and the NON ketotic hyperglycinemia pathway. Phosphohydroxypyruvic acid is a prduct of both enzyme phosphoglycerate dehydrogenase [EC 1.1.1.95] and phosphoserine transaminase [EC 2.6.1.52] in glycine, serine and threonine metabolism pathway (KEGG).3913-50-6C03232105309333-P-HYDROXYPYRUVATE103OC(=O)C(=O)COP(O)(O)=OC3H5O7PInChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)LFLUCDOSQPJJBE-UHFFFAOYSA-N2-oxo-3-(phosphonooxy)propanoic acid184.0414183.977289026-1.143phosphohydroxypyruvate0-3FDB0223772-oxo-3-(phosphonooxy)-propanoate;2-oxo-3-(phosphonooxy)-propanoic acid;3-phosphohydroxypyruvate;3-phosphohydroxypyruvic acid;3-phosphonooxypyruvate;3-phosphonooxypyruvic acid;Phosphohydroxypyruvate;Phosphohydroxypyruvic acid;Hydroxypyruvic acid phosphate;2-oxo-3-phosphonooxypropanoate;Hydroxypyruvate phosphate;Hydroxypyruvic acid phosphoric acid;3-phosphonatooxypyruvatePW_C0008103POHPyr347927810813212215712412470911812631529912787638895L-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_C000095Glu16244365811911384164149699110542144850145626146254532311153441135415117543911855651325631107563210858591056006147607115761919465318568381876844188709272709371716520571822077514224751815182082258373220117921981185516112004222126213112683289126972904234831542349318428453207702025377332133775251127797134677977327779813477829134580649135120023124120040122120086407120347406120692126120816418121147423121153424121157425122833119122997120123299443123401454123719458123725459123729460125401299125418297125457481125667479125769301125802489126941388126995206127162501127257506134Oxoglutaric 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;Ī±-ketoglutarate;Ī±-ketoglutaric acidPW_C000134AKG15242314141468499186733111084212635144750145526146754537510354141175438118556413260081476036155606915760921616482178653085747122275152247519151820922583742201186319812681289770542537713513377481111775231127774612977967345779703467797632777984347784253348001836880694135113162941199724061200221241200844071201741221205524141208144181209894081211464231211524241211604251227571201228311191231864501233994541235543741237184581237244591237324601253574791254002991254554811255332971258004891259294821269005011269403881269932061270662051272555061273885021214DL-O-PhosphoserineHMDB0001721It is a normal metabolite found in human biofluids. (PMID 7693088, 7688003). The phosphoric ester of serine. -- Pubchem. Serine is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Phosphorylated serine residues are often referred to as phosphoserine. Serine proteases are a common type of protease. - Wikipedia.17885-08-4C01005106377123-P-SERINE104NC(COP(O)(O)=O)C(O)=OC3H8NO6PInChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)BZQFBWGGLXLEPQ-UHFFFAOYSA-N2-amino-3-(phosphonooxy)propanoic acid185.0725185.008923505-0.974P-serine0-2FDB0227003-phospho-1-serine;3-phospho-serine;3-phosphoserine;Dl-o-phosphorylserine;Dl-o-phosphoserine;Dl-o-serine phosphate;Dl-serine dihydrogen phosphate;Dl-serine monophosphorate;Dl-serine monophosphoric acid;Energoserina;O-phospho-dl-serine;O-phospho-l-serine;O-phosphonoserine;P-serine;Phosphorylserine;Phosphoserine;Serine phosphate;Serine-3-phosphate;Serophen;2-amino-3-(phosphonooxy)propanoic acid;Dl-serine, dihydrogen phosphate (ester);2-amino-3-(phosphonooxy)propanoate;Dl-serine dihydrogen phosphoric acid;Dl-serine, dihydrogen phosphoric acid (ester)PW_C001214DL-OPPr6516108652010742588318425893151420WaterHMDB0002111Water 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_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131104PhosphateHMDB0001429Phosphate 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-85871032[O-]P([O-])([O-])=OO4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3NBIIXXVUZAFLBC-UHFFFAOYSA-Kphosphoric acid94.971494.953423phosphoric 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_C001104Pi2448488145818188312980317631417674925001027294727374631292931667236366138512342492244753150312751587520797521610053171115351112538110354471205543129557313356051355625108569365848143585514659111475941151604015561001616294107648717866911016714117684218868891607161205718920672122117306198738921074022127436163747522281962258258227101182411013425711748132117611151177321311904170119271641201428112728290132632233481917422553044235031542435318436923227701825377194293772171347794033677966130780483327805732978245353786693318002236889279308938313839479638411055839011064039111323594115845398116206109119982406120069122120699407121057124121216125121268429121352121121409123121423382121852405123304119123621118123786136123838464123968447123981399124405376124948472125362479125446297125774481125954299126221478126594300126604298126723484126904501127413388127783209128166395128177513128315389120L-SerineHMDB0000187Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. (http://www.dcnutrition.com/AminoAcids/) L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373).56-45-1C00065595117115SER5736DB00133N[C@@H](CO)C(O)=OC3H7NO3InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1MTCFGRXMJLQNBG-REOHCLBHSA-N(2S)-2-amino-3-hydroxypropanoic acid105.0926105.0425930950.663L-serine00FDB012739(-)-serine;(s)-2-amino-3-hydroxypropanoate;(s)-2-amino-3-hydroxypropanoic acid;(s)-2-amino-3-hydroxy-propanoate;(s)-2-amino-3-hydroxy-propanoic acid;(s)-serine;(s)-a-amino-b-hydroxypropionate;(s)-a-amino-b-hydroxypropionic acid;(s)-alpha-amino-beta-hydroxypropionate;(s)-alpha-amino-beta-hydroxypropionic acid;(s)-b-amino-3-hydroxypropionate;(s)-b-amino-3-hydroxypropionic acid;(s)-beta-amino-3-hydroxypropionate;(s)-beta-amino-3-hydroxypropionic acid;2-amino-3-hydroxypropanoate;2-amino-3-hydroxypropanoic acid;3-hydroxy-l-alanine;L-(-)-serine;L-3-hydroxy-2-aminopropionate;L-3-hydroxy-2-aminopropionic acid;L-3-hydroxy-alanine;L-ser;Serine;B-hydroxy-l-alanine;Beta-hydroxy-l-alanine;Beta-hydroxyalanine;(2s)-2-amino-3-hydroxypropanoic acid;(s)-(-)-serine;L-2-amino-3-hydroxypropionic acid;L-serin;S;Ser;(2s)-2-amino-3-hydroxypropanoate;(s)-Ī±-amino-Ī²-hydroxypropionate;(s)-Ī±-amino-Ī²-hydroxypropionic acid;Ī²-hydroxy-l-alanine;B-hydroxyalanine;Ī²-hydroxyalanine;L-2-amino-3-hydroxypropionatePW_C000120Ser34481810226174564210756431085884105601114769071637086201708720270907170917272021607438374431574441667522224835722591542491217315112625181537949423353184233631577320111780881337811213279979331948583831157523981199241221220561241221364061227181351246671181246881201253142971262092991262934791268602051277713881278565011221Tetrahydrofolic acidHMDB0001846Tetrahydrofolate is a soluble coenzyme (vitamin B9) that is synthesized de novo by plants and microorganisms, and absorbed from the diet by animals. It is composed of three distinct parts: a pterin ring, a p-ABA (p-aminobenzoic acid) and a polyglutamate chain with a number of residues varying between 1 and 8. Only the tetra-reduced form of the molecule serves as a coenzyme for C1 transfer reactions. In biological systems, the C1-units exist under various oxidation states and the different tetrahydrofolate derivatives constitute a family of related molecules named indistinctly under the generic term folate. (PMID 16042593). Folate is important for cells and tissues that rapidly divide. Cancer cells divide rapidly, and drugs that interfere with folate metabolism are used to treat cancer. Methotrexate is a drug often used to treat cancer because it inhibits the production of the active form, tetrahydrofolate. Unfortunately, methotrexate can be toxic, producing side effects such as inflammation in the digestive tract that make it difficult to eat normally. -- Wikipedia; Signs of folic acid deficiency are often subtle. Diarrhea, loss of appetite, and weight loss can occur. Additional signs are weakness, sore tongue, headaches, heart palpitations, irritability, and behavioral disorders. Women with folate deficiency who become pregnant are more likely to give birth to low birth weight and premature infants, and infants with neural tube defects. In adults, anemia is a sign of advanced folate deficiency. In infants and children, folate deficiency can slow growth rate. Some of these symptoms can also result from a variety of medical conditions other than folate deficiency. It is important to have a physician evaluate these symptoms so that appropriate medical care can be given. -- Wikipedia; Folinic acid is a form of folate that can help 'rescue' or reverse the toxic effects of methotrexate. Folinic acid is not the same as folic acid. Folic acid supplements have little established role in cancer chemotherapy. There have been cases of severe adverse effects of accidental substitution of folic acid for folinic acid in patients receiving methotrexate cancer chemotherapy. It is important for anyone receiving methotrexate to follow medical advice on the use of folic or folinic acid supplements. -- Wikipedia. Low concentrations of folate, vitamin B12, or vitamin B6 may increase the level of homocysteine, an amino acid normally found in blood. There is evidence that an elevated homocysteine level is an independent risk factor for heart disease and stroke. The evidence suggests that high levels of homocysteine may damage coronary arteries or make it easier for blood clotting cells called platelets to clump together and form a clot. However, there is currently no evidence available to suggest that lowering homocysteine with vitamins will reduce your risk of heart disease. Clinical intervention trials are needed to determine whether supplementation with folic acid, vitamin B12 or vitamin B6 can lower your risk of developing coronary heart disease. -- Wikipedia.135-16-0C001011378185720506THF18714427DB00116NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)N2)N1C19H23N7O6InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12?/m0/s1MSTNYGQPCMXVAQ-PXYINDEMSA-N2-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid445.4292445.170981503-3.2282-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid0-2FDB022705(6s)-tetrahydrofolate;(6s)-tetrahydrofolic acid;5,6,7,8-tetrahydrofolate;5,6,7,8-tetrahydrofolic acid;Tetra-h-folate;Tetrahydrafolate;Tetrahydrofolate;Tetrahydrofolic acid;Tetrahydropteroyl mono-l-glutamate;TetrahydropteroylglutamatePW_C001221THFA448457189753180925307111534711256011355786108600914770661887151205718520675831631179719842640315773361337811813212035240612048212212069640712216612412300112012330111912471811812567347912574929712577148112632429912716850112788638878GlycineHMDB0000123Glycine is a simple, nonessential amino acid, although experimental animals show reduced growth on low-glycine diets. The average adult ingests 3 to 5 grams of glycine daily. Glycine is involved in the body's production of DNA, phospholipids and collagen, and in release of energy. Glycine levels are effectively measured in plasma in both normal patients and those with inborn errors of glycine metabolism. (http://www.dcnutrition.com/AminoAcids/) Nonketotic hyperglycinaemia (OMIM 606899) is an autosomal recessive condition caused by deficient enzyme activity of the glycine cleavage enzyme system (EC 2.1.1.10). The glycine cleavage enzyme system comprises four proteins: P-, T-, H- and L-proteins (EC 1.4.4.2, EC 2.1.2.10 and EC 1.8.1.4 for P-, T- and L-proteins). Mutations have been described in the GLDC (OMIM 238300), AMT (OMIM 238310), and GCSH (OMIM 238330) genes encoding the P-, T-, and H-proteins respectively. The glycine cleavage system catalyses the oxidative conversion of glycine into carbon dioxide and ammonia, with the remaining one-carbon unit transferred to folate as methylenetetrahydrofolate. It is the main catabolic pathway for glycine and it also contributes to one-carbon metabolism. Patients with a deficiency of this enzyme system have increased glycine in plasma, urine and cerebrospinal fluid (CSF) with an increased CSF: plasma glycine ratio. (PMID 16151895).56-40-6C00037525712715428GLY730DB00145NCC(O)=OC2H5NO2InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)DHMQDGOQFOQNFH-UHFFFAOYSA-N2-aminoacetic acid75.066675.0320284090.872glycine00FDB0004842-aminoacetate;2-aminoacetic acid;Aciport;Amino-acetate;Amino-acetic acid;Aminoacetate;Aminoacetic acid;Aminoethanoate;Aminoethanoic acid;Glicoamin;Glycocoll;Glycolixir;Glycosthene;Gyn-hydralin;Padil;Aminoessigsaeure;G;Gly;Glycin;Glykokoll;Glyzin;H2n-ch2-cooh;Hgly;LeimzuckerPW_C000078Gly31417981812218812728292954201035454120558013356401075641108586310560071477014160743937441166744215117941981187216112429151152332224241931842420315776443367774211178022132783043518070813512002840612009712212011712412168742912228343512285011812423646412483747012540647912546629712548429912644849912694650112700320512702138812801851711785,10-Methylene-THFHMDB00015335,10-Methylene-THF is an intermediate in glycine, serine and threonine metabolism and one carbon metabolism. 5,10-CH2-THF can also be used as a coenzyme in the biosynthesis of thymidine. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase. 5,10-Methylene-THF is a substrate for Methylenetetrahydrofolate reductase. This enzyme converts 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate. This reaction is required for the multistep process that converts the amino acid homocysteine to methionine. The body uses methionine to make proteins and other important compounds. 5,10-CH2-THF is a substrate for many enzymes including Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), Aminomethyltransferase (mitochondrial), Serine hydroxymethyltransferase (mitochondrial), Methylenetetrahydrofolate reductase, C-1-tetrahydrofolate synthase (cytoplasmic), Serine hydroxymethyltransferase (cytosolic) and Thymidylate synthase.3432-99-3C0014343917515636METHYLENE-THF388320[H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)NC(CCC(O)=O)C(O)=OC20H23N7O6InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13?/m1/s1QYNUQALWYRSVHF-PZORYLMUSA-N2-({4-[(6aR)-3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid457.4399457.170981503-2.7562-({4-[(6aR)-3-amino-1-oxo-2H,5H,6H,6aH,7H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid0-2FDB022675(6r)-5,10-methylenetetrahydrofolate;5,10-methenyltetrahydropteroylglutamate;5,10-methylene-6-hydrofolate;5,10-methylene-6-hydrofolic acid;5,10-methylene-thf;5,10-methylenetetrahydrofolate;5,10-methylenetetrahydrofolic acid;N5>,n10-methylenetetrahydrofolate;(6r)-5,10-methylenetetrahydrofolic acidPW_C0011785XM-THF449495689853181125331111535911257851086010147627235706518871712057196206758216342639315773391337811913212035540612068312212070440712216712412300412012329313512330911912471911812567647912576129712577948112632529912717150112788738822608AmmoniumHMDB0041827Ammonium is an important source of nitrogen for many plant species, especially those growing on hypoxic soils. However, it is also toxic to most crop species and is rarely applied as a sole nitrogen source. The ammonium (more obscurely: aminium) cation is a positively charged polyatomic cation with the chemical formula NH4+. It is formed by the protonation of ammonia (NH3). Ammonium is also a general name for positively charged or protonated substituted amines and quaternary ammonium cations (NR4+), where one or more hydrogen atoms are replaced by organic radical groups (indicated by R).14798-03-9C013421674114628938218[NH4+]H4NInChI=1S/H3N/h1H3/p+1QGZKDVFQNNGYKY-UHFFFAOYSA-Oazanium18.038518.0343741331azanium11Ammonium ion;Ammonia ion;Ammonium;Ammonium chloride;Ammonium(1+);Azanium;Nh4+;[nh4]+;[nh4](+);Nh4(+)PW_C022608Ammon57511085892955969100622616682731518367225119091701247024942627315116281109143NADPHMDB0000217Nicotinamide 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](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O17P3InChI=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)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-O1-[(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)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium744.4129744.083277073-2.2791-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-3FDB021908Adenine-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;Ī²-nicotinamide adenine dinucleotide phosphate;Ī²-nicotinamide adenine dinucleotide phosphoric acidPW_C000143NADP183819137685780108241883921611291617494685314796144801145308111579010860171476132159627335677811770691887105163715220572061607317213734621075622127589170819722582201518419224118111981189721112008222121521641224928612597226126502494234431543745322769132937716413277384331773963327746113077515115776243367781433477870112807131191131659412010640712042940512045012212060440812061812312114212512127742912140112412148538312306337612308413512322937412324344712371313612384846412396011812404339812547348112569429712574348212621529912652849512701020612722550212757038812810039010455,10-Methenyltetrahydrofolic acidHMDB0001354Folate is important for cells and tissues that rapidly divide. Cancer cells divide rapidly, and drugs that interfere with folate metabolism are used to treat cancer. Methotrexate is a drug often used to treat cancer because it inhibits the production of the active form, tetrahydrofolate. Unfortunately, methotrexate can be toxic, producing side effects such as inflammation in the digestive tract that make it difficult to eat normally. Folinic acid is a form of folate that can help 'rescue' or reverse the toxic effects of methotrexate. Folinic acid is not the same as folic acid. Folic acid supplements have little established role in cancer chemotherapy. There have been cases of severe adverse effects of accidental substitution of folic acid for folinic acid in patients receiving methotrexate cancer chemotherapy. It is important for anyone receiving methotrexate to follow medical advice on the use of folic or folinic acid supplements. Low concentrations of folate, vitamin B12, or vitamin B6 may increase your level of homocysteine, an amino acid normally found in your blood. There is evidence that an elevated homocysteine level is an independent risk factor for heart disease and stroke. The evidence suggests that high levels of homocysteine may damage coronary arteries or make it easier for blood clotting cells called platelets to clump together and form a clot. However, there is currently no evidence available to suggest that lowering homocysteine with vitamins will reduce your risk of heart disease. Clinical intervention trials are needed to determine whether supplementation with folic acid, vitamin B12 or vitamin B6 can lower your risk of developing coronary heart disease. Methylene tetrahydrofolate (CH2FH4) is formed from tetrahydrofolate by the addition of methylene groups from one of three carbon donors: formaldehyde, serine, or glycine. Methyl tetrahydrofolate(CH3FH4) can be made from methylene tetrahydrofolate by reduction of the methylene group, and formyl tetrahydrofolate (CHOFH4, folinic acid) is made by oxidation of methylene tetrahydrofolate. In the form of a series of tetrahydrofolate compounds, folate derivatives are substrates in a number of single-carbon-transfer reactions, and also are involved in the synthesis of dTMP (2'-deoxythymidine-5'-phosphate) from dUMP (2'-deoxyuridine-5'-phosphate). It helps convert vitamin B12 to one of its coenzyme forms and helps synthesize the DNA required for all rapidly growing cells.7444-29-3C00445644350156365,10-methenyl-thf559356[H][C@@]12CN(C=[N+]1C1=C(NC2)NC(N)=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C([O-])=OC20H21N7O6InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1MEANFMOQMXYMCT-OLZOCXBDSA-N(6aR)-3-amino-8-(4-{[(1S)-3-carboxy-1-carboxylatopropyl]carbamoyl}phenyl)-1-oxo-1H,4H,5H,6H,6aH,7H,8H-10Ī»āµ-imidazo[1,5-f]pteridin-10-ylium455.424455.155331439-3.395(6aR)-3-amino-8-(4-{[(1S)-3-carboxy-1-carboxylatopropyl]carbamoyl}phenyl)-1-oxo-4H,5H,6H,6aH,7H-10Ī»āµ-imidazo[1,5-f]pteridin-10-ylium0-2FDB0225735,10-methenyl-thf;5,10-methenyltetrahydrofolate;Anhydro-leucovorin;Anhydro-leucovorin a;Anhydroleucovorin;Anhydroleucovorin a;Ch-thf;Methenyl-tetrahydrofolate;Methenyl-thf;Methenyltetrahydrofolate;Methenyltetrahydrofolic acid;N5-n10-ch-thf;N5-n10-methenyltetrahydrofolatePW_C001045CH-THF953898235328111535411271692057192206120681122120701407123291135123306119125759297125776481146NADPHHMDB0000221Nicotinamide 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=C(N)N=CN=C23)[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-/m0/s1ACFIXJIJDZMPPO-NCHANQSKSA-N{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-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 acid745.4209745.091102105-2.149[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid0-4FDB0219092'-(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_C000146NADPH1858190377810796582118837216092916154946873147931447971453101115789108597214761281596271356779117706818871031637154205720516073152137345210755921275911708194225821915184212241181219811893211120062221215016412245286125962261264824942343315437463227691129377166132773853317739433277460130775041127751111577623336807121191131649412010540712042540512045212212061612312114112512127542912140212412148338312305937612308613512324144712371213612384646412396111812404139812547248112569629712621429912652949512700920612757238812810139077410-FormyltetrahydrofolateHMDB000097210-Formyltetrahydrofolate (10-CHO-THF) is form of tetrahydrofolate that acts as a donor of formyl groups in anabolism. In particular, 10-CHO-THF is used as a substrate in a number of formyltransferase reactions. It plays an important role in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase, as well as in the formylation of the methionyl initiator tRNA (fMet-tRNA), when 10-CHO-THF is a substrate for methionyl-tRNA formyltransferase. 10-Formyltetrahydrofolate is a substrate for Trifunctional purine biosynthetic protein adenosine-3, Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), 10-formyltetrahydrofolate dehydrogenase, Folylpolyglutamate synthase (mitochondrial), Bifunctional purine biosynthesis protein PURH and C-1-tetrahydrofolate synthase (cytoplasmic).2800-34-2C002341223471563710-FORMYL-THF109092NC1=NC(=O)C2=C(NCC(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1C20H23N7O7InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1AUFGTPPARQZWDO-YUZLPWPTSA-N(2S)-2-[(4-{N-[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid473.4393473.165896125-3.157(2S)-2-[(4-{N-[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid0-2FDB02234510-formyl-(6rs)-tetrahydrofolic acid;10-formyl-h4pteglu1;10-formyl-thf;10-formyl-tetrahydrofolate;10-formyltetrahydrofolate;10-formyltetrahydrofolic acid;10-formyltetrahydropteroylglutamate;10-formyltetrahydropteroylglutamic acid;10-fthf;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamate;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamic acid;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-l-glutamate;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-l-glutamic acid;N10-formyl-5,6,7,8-tetrahydrofolate;N10-formyl-5,6,7,8-tetrahydrofolic acid;N10-formyltetrahydrofolate;N10-formyltetrahydrofolic acid;N10-formyltetrahydropteroylglutamate;N10-formyl-h4f;N10-formyl-thfPW_C00077410-FTHF94789793191825316111535011271602057188206744016611796198783221321206711221206984071223011241232851351233031191248531181257542971257734811264672991280373881034Adenosine 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_C001034ADP234134841522482138015963159783106114151821901492104182113102161582408592435272728472736462855293165723635614400234476314770915036265157752089752171005315111534911253921035446120554412955721335624108574111757641015849143585614658781075899147592615160501556111161623116664951786700946841188687216071592057187206720821072262137231211730019873032167391217741021874331637483222818722511851277119051701201328112180285132622231532930842328315423983134262232242696318770292537708713277216134773063297747233377663336780393327804335078170128782153517824435378414335784951157870533178849130789203348003036880622118806511358067611994827124113283388116204109119944122119994406120156407120318382120366412121248429121394123121399433121472408121899383121976410122064125122085405122405422122445435122973399123013446123818464123953447123958468124030374124452398124529444124615136124636376124947472124975375125012470125334297125373479125492299125517481125645484126125485126219300126235495126242478126550491126597499126915501127733516127780395127797390127803209128122508128168517128313389414Adenosine 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_C000414ATP9221460826616414224781373332799593439976321051821121021464921561421605824055924342727264628122930296631637236166136175143992344743147689148645450328950352651557520597521510052501045291101531311153461125390103540611754301185443120554212955561325569133560313556211085846143585414658761075897147592415160481556109161623016664931786839188687016069761997157205718420672092107225213722921172981987302216739021774082187432163748122274991908186225118472771190317012010281120391641217828512578226126912901326422315327308423263154262132242694318770282537721813477233329774683337763233678037332780413507816812878214351782403537841133578494115788501307886533178919334800283688004618480674119856291948261241132349411328238811628010911991412211999240612015440712024538212036241212124642912139212312139743312147140812197441012206512512207938312208340512240242212244443512291939912300944612381646412395144712395646812402937412452744412461613612463039812463437612494347212497237512501147012530429712537147912539229912551548112559548412612348512622030012623449512624047812654749112659649912691350112712338912773151612778139512779639012780120912811950812816751792Formic acidHMDB0000142Formic acid is the simplest carboxylic acid. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a byproduct in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer.64-18-6C000581897100230751FORMATE278DB01942OC=OCH2O2InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)BDAGIHXWWSANSR-UHFFFAOYSA-Nformic acid46.025446.0054793081.021formic acid0-1DBMET00489FDB012804Add-f;Ameisensaure;Aminate;Aminic acid;Bilorin;Collo-bueglatt;Collo-didax;Formate;Formira;Formisoton;Formylate;Formylic acid;Hydrogen carboxylate;Hydrogen carboxylic acid;Methanoate;Methanoic acid;Methanoic acid monomer;Myrmicyl;Sodium formate;Sybest;Wonderbond hardener m 600lPW_C000092Formate9468977316294919432531411153481126636107715820571862067325213761616082872101198215143522318769632257865213278934331120670122120697407121496383121751124123284135123302119124054398124302118125753297125772481126478299126821495127637388128426390409212-aminoprop-2-enoate2-Aminoprop-2-enoate, also known as 2-aminoacrylate or 2,3-didehydroalaninate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 2-Aminoprop-2-enoate is soluble (in water) and a moderately acidic compound (based on its pKa). 2-Aminoprop-2-enoate may be a unique E.coli metabolite. 2-Aminoprop-2-enoate participates in a number of enzymatic reactions. In particular, Homocysteine and 2-aminoprop-2-enoate can be biosynthesized from L-cystathionine through the action of the enzymes bifunctional Ī²-cystathionase, PLP-dependent and regulator OF maltose regulon and cystathionine-Ī²-lyase / L-cysteine desulfhydrase. In addition, Hydrogen sulfide and 2-aminoprop-2-enoate can be biosynthesized from L-cysteine through the action of the enzyme tryptophanase / L-cysteine desulfhydrase.58020 NC(=C)C([O-])=OC3H4NO2InChI=1S/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6)/p-1UQBOJOOOTLPNST-UHFFFAOYSA-M2-aminoprop-2-enoate86.07186.0247519530.401Ī±-aminoacrylate-10PW_C0409212A2E82632258365151409282-iminopropanoate2-Iminopropanoate belongs to the class of organic compounds known as ketimines. These are organic compounds bearing the ketimine functional group, with the general structure R2C=NR' ( R is not a hydrogen ). 2-Iminopropanoate is slightly soluble (in water) and a weakly acidic compound (based on its pKa).77456CC(=N)C([O-])=OC3H4NO2InChI=1S/C3H5NO2/c1-2(4)3(5)6/h4H,1H3,(H,5,6)/p-1DUAWRLXHCUAWMK-UHFFFAOYSA-M2-iminopropanoate86.07186.024751953-1.2112-iminopropanoate-10PW_C0409282-Isopa8366151164Pyruvic 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;Ī±-ketopropionate;Ī±-ketopropionic acid;A-oxopropionsaeure;Ī±-oxopropionsaeurePW_C000164Pyr17220442281181314495014572653651035405117544011854441205566132557013358939559201475951151602215560671566074161612616063831646717865101776532857457222749522082002251262231152922491534918773101117797234677978327780901128000436880042367806951351128799411568312111995040612001112412017512212087840712114842312115442412345411912372045812372645912534047912539029912553429712585448112688350112693138812706720512785820610598D-3-phosphoglycerate dehydrogenase 2P40510SER33291.1.1.95780716010599D-3-phosphoglycerate dehydrogenase 1P40054SER3291.1.1.95780816010600Phosphoserine aminotransferaseP33330
Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine.
SER1292.6.1.52780916010601phosphoserine phosphataseP42941SER2293.1.3.3781316010603Serine hydroxymethyltransferase, mitochondrialP37292
Interconversion of serine and glycine.
SHM1292.1.2.1781416310602Serine hydroxymethyltransferaseP37291
Interconversion of serine and glycine.
SHM2292.1.2.1781216010604Aminomethyltransferase, mitochondrialP48015
The glycine cleavage system (glycine decarboxylase complex) catalyzes the degradation of glycine.
GCV1292.1.2.10781516310605mitochondrial C1-tetrahydrofolate synthaseP09440MIS1291.5.1.5; 3.5.4.9; 6.3.4.37816163897924310617Catabolic L-serine/threonine dehydrataseP25379CHA1294.3.1.17; 4.3.1.19798016022994Sideroflexin FSF1Q12029
Mitochondrial amino-acid transporter that mediates transport of serine into mitochondria.
FSF12943043-phosphoglycerate dehydrogenase18PW_P004304113591059811360105994305phosphoserine transaminase18PW_P00430511361106004306phosphoserine phosphatase18PW_P00430611362106014308Serine hydroxymethyltransferase, mitochondrial18PW_P00430811364106034307Serine hydroxymethyltransferase18PW_P00430711363106024309Aminomethyltransferase18PW_P00430911365106044310mitochondrial C1-tetrahydrofolate synthase18PW_P00431011366106054324serine deaminase18PW_P004324113811061713618Sideroflexin29PW_P01361823490229941372551626364falsePW_R006364Right260596441Compoundfalse260607211Compoundfalse2606111441Compoundfalse26062400341Compoundfalse260638101Compoundfalse629043041.1.1.956365falsePW_R006365Right260648101Compoundfalse26065951Compoundfalse260661341Compoundfalse2606712141Compoundfalse629143052.6.1.526366falsePW_R006366Right2606812141Compoundfalse2606914201Compoundfalse2607011041Compoundfalse260711201Compoundfalse629243063.1.3.36368falsePW_R006368Right260771201Compoundtrue2607812211Compoundfalse2607914201Compoundtrue26080781Compoundtrue2608111781Compoundfalse629443082.1.2.16367falsePW_R006367Right260721201Compoundtrue2607312211Compoundfalse2607414201Compoundtrue26075781Compoundtrue2607611781Compoundfalse629343072.1.2.16369falsePW_R006369Right26082781Compoundfalse2608312211Compoundfalse26084226081Compoundfalse2608511781Compoundfalse629543092.1.2.106370falsePW_R006370Right2608611781Compoundfalse260871431Compoundfalse2608810451Compoundfalse260891461Compoundfalse629643101.5.1.5,3.5.4.9, 6.3.4.36371falsePW_R006371Right2609010451Compoundfalse2609114201Compoundfalse260927741Compoundfalse26093400341Compoundfalse629743106372falsePW_R006372Right260947741Compoundfalse2609510341Compoundfalse2609611041Compoundfalse260974141Compoundfalse26098921Compoundfalse2609912211Compoundfalse629843106385falsePW_R006385Right261571201Compoundfalse2615814201Compoundfalse26159400341Compoundfalse26160409211Compoundfalse631143244.3.1.17,4.3.1.196146truePW_R006146Right25152409211Compoundfalse25153409281Compoundfalse2903truePW_R002903Right11530409281Compoundfalse1153114201Compoundfalse11532400341Compoundfalse11533226081Compoundfalse115341641Compoundfalse528PW_T0005286721201Compound188163Right1586136182019-08-12T12:13:58-06:002019-08-12T12:13:58-06:00162779596443false29845410regular1001207796072159false43344910regular503077961114460false73344810regular5030779624003455false68955310regular7878779638103false82345610regular10011077964953false93832610regular100110779651343false122356610regular1001107796612143false134845610regular10011077967142049false144058210regular787877968110446false145080410regular4443779691203false134986610regular100100779741201633false1354140110regular1001007797512213false1469130610regular10011077976142049false1745150210regular787877977783false1874140010regular1001007797811783false1734130010regular1001107797912213false122975610regular10011077980142049false92079710regular787877981783false74986510regular1001007798211783false87496010regular1001107798312213false1999150010regular10011077984226083false2289150510regular1001007798511783false2404139510regular1001107798614361false2489153510regular50307798710453false2404180010regular1001207798814662false2489173010regular503077989142049false2310173710regular7878779907743false1919180810regular100110779914003455false2050190310regular787877992103443false1849179510regular503077993110446false1857191010regular44437799441442false1559191610regular503077995923false1414181610regular1001007799612213false1539171610regular10011077997142049false168579610regular7878779984003455false169095410regular787877999409213false179986210regular10011078000409283false199486210regular10011078001142049false212097610regular7878780024003455false211580910regular787878003226083false227978110regular100100780041643false239486610regular10010037448105981602false5534278subunitregular1507037449105991602false5134778subunitregular1507037450106002false10484768subunitregular1507037451106011602false13236888subunitregular1507037453106031632false157414138subunitregular1507037454106021602false10498788subunitregular1507037455106041632false211914128subunitregular1507037456106052432false238116128subunitregular1507037457106051632false214418258subunitregular1507037458106051632false165918318subunitregular1507037459106171602false14998818subunitregular150709790062299476false132911938subunitregular15070305374304215936785374483678637449305384305215936787374503053943062159367883745130541430821593679037453305424307215936791374543054343092159367923745530544431021593679337456305454310215936794374573054643102159367953745830547432421593679637459828740136182159974771979006112280M398 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688 5false18112291M1450 825.5 C1393 826.5 1398 788 1398 758 5false18trueM 953.9468550441649 13.26155629629604 L 939 12 L 945.3808877211858 25.575134323078345false112292M1399 866 C1399 836 1398 788 1398 758 5false18trueM 953.9468550441649 13.26155629629604 L 939 12 L 945.3808877211858 25.575134323078345false112300M1454 1451 C1484 1451 1544 1451 1574 1451 5false18112301M1519 1416 C1521 1452 1544 1448 1574 1448 5false18112302M1784 1502 C1782 1456 1758 1450 1724 1448 5false18trueM 1378.9468550441647 1011.261556296296 L 1364 1010 L 1370.380887721186 1023.5751343230784false112303M1874 1450 C1844 1450 1754 1449 1724 1448 5false18trueM 1378.9468550441647 1011.261556296296 L 1364 1010 L 1370.380887721186 1023.5751343230784false112304M1784 1410 C1783 1441 1766 1448 1724 1448 5false18trueM 1378.9468550441647 1011.261556296296 L 1364 1010 L 1370.380887721186 1023.5751343230784false112305M1349 916 C1299 916 1235 913 1199 913 5false18112306M1279 866 C1277 907 1239 913 1199 913 5false18112307M959 875 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