2205PathwayCardiolipin BiosynthesisThe biosynthesis of cardiolipin (CL) begins in the endoplasmic reticulum. Glycerone phosphate interacts with an NADPH resulting in the release of NADP and glycerol 3-phosphate. Glycerol 3-phosphate reacts with glycerol-3-phosphate O-acyltransferase resulting in the release of 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid or LysoPA). The resulting compound reacts with an acyl-CoA via lysophosphatidate acyltransferase, resulting in the release of a phosphatidic acid (PA or 1,2-diacyl-sn-glycerol 3-phosphate). Phosphatidic acid is transported to the mitochondrial outer membrane. Once in, it gets transported into the mitochondrial inner membrane. The phosphatidic acid reacts with cytidine triphosphate through a phosphatidate cytidyltransferase resulting in the release of a CDP-diacylglycerol (CDP-DG). The resulting compound reacts with a glycerol 3-phosphate through a CDP-diacylglycerol-glycerol-3-phosphate 3-phosphatidyltransferase resulting in the release of cytidine monophosphate and phosphatidylglycerophosphate (PGP). PGP reacts with phosphatidylglycerophosphatase GEP4 resulting in the release of phosphatidylglycerol (PG). PG reacts with a CDP-DG through a cardiolipin synthase resulting in the release of CL and cytidine monophosphate. Cardiolipin remodelling begins with the removal of an acyl chain to form 1-monolysocardiolipin (1-MLCL) via the lipase Cld1p. This is followed by the enzyme Taz1p transferring an acyl chain from a phospholipid (e.g. phosphatidylcholine) to reform cardiolipin.MetabolicPW002431CenterPathwayVisualizationContext271728502050#000099PathwayVisualization21882205Cardiolipin BiosynthesisThe biosynthesis of cardiolipin (CL) begins in the endoplasmic reticulum. Glycerone phosphate interacts with an NADPH resulting in the release of NADP and glycerol 3-phosphate. Glycerol 3-phosphate reacts with glycerol-3-phosphate O-acyltransferase resulting in the release of 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid or LysoPA). The resulting compound reacts with an acyl-CoA via lysophosphatidate acyltransferase, resulting in the release of a phosphatidic acid (PA or 1,2-diacyl-sn-glycerol 3-phosphate). Phosphatidic acid is transported to the mitochondrial outer membrane. Once in, it gets transported into the mitochondrial inner membrane. The phosphatidic acid reacts with cytidine triphosphate through a phosphatidate cytidyltransferase resulting in the release of a CDP-diacylglycerol (CDP-DG). The resulting compound reacts with a glycerol 3-phosphate through a CDP-diacylglycerol-glycerol-3-phosphate 3-phosphatidyltransferase resulting in the release of cytidine monophosphate and phosphatidylglycerophosphate (PGP). PGP reacts with phosphatidylglycerophosphatase GEP4 resulting in the release of phosphatidylglycerol (PG). PG reacts with a CDP-DG through a cardiolipin synthase resulting in the release of CL and cytidine monophosphate. Cardiolipin remodelling begins with the removal of an acyl chain to form 1-monolysocardiolipin (1-MLCL) via the lipase Cld1p. This is followed by the enzyme Taz1p transferring an acyl chain from a phospholipid (e.g. phosphatidylcholine) to reform cardiolipin.Metabolic18554624184646Baile MG, Lu YW, Claypool SM: The topology and regulation of cardiolipin biosynthesis and remodeling in yeast. Chem Phys Lipids. 2014 Apr;179:25-31. doi: 10.1016/j.chemphyslip.2013.10.008. Epub 2013 Nov 1.2205Pathway1CellCL:00000005HepatocyteCL:00001824Cardiomyocyte CL:00007463NeuronCL:00005407Epithelial CellCL:00000661Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote18Saccharomyces cerevisiae4932EukaryoteYeast4Arabidopsis thaliana3702EukaryoteThale cress23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle6Caenorhabditis elegans6239EukaryoteRoundworm17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly24Solanum lycopersicum4081EukaryoteTomato21Xenopus laevis8355EukaryoteAfrican clawed frog60Nitzschia sp.0001EukaryoteNitzschia42Bacteria2ProkaryoteBacteria25Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel51Picea sitchensis3332EukaryoteSitka spruce19Schizosaccharomyces pombe4896Eukaryote29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast5CytoplasmGO:00057371CytosolGO:000582924Mitochondrial Intermembrane SpaceGO:000575814Mitochondrial Outer MembraneGO:000574131Periplasmic SpaceGO:000562012Mitochondrial Inner MembraneGO:000574313Endoplasmic ReticulumGO:00057833Mitochondrial MatrixGO:00057592MitochondrionGO:000573927Peroxisome MembraneGO:00057784PeroxisomeGO:00057778Smooth Endoplasmic Reticulum GO:00057907Endoplasmic Reticulum MembraneGO:000578910Cell MembraneGO:000588611Extracellular SpaceGO:000561535ChloroplastGO:000950736MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032532Inner MembraneGO:007025815NucleusGO:00056346LysosomeGO:000576416Lysosomal LumenGO:004320218Melanosome MembraneGO:003316225Golgi apparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520240PeriplasmGO:004259719sarcoplasmic reticulumGO:001652926Golgi apparatus membraneGO:00001391LiverBTO:000075972928StomachBTO:0001307155268Blood VesselBTO:000110274114Adrenal MedullaBTO:000004971825IntestineBTO:00006487Nervous SystemBTO:000148411HeartBTO:000056273108511PW_BS0000082111PW_BS000002422411PW_BS0000425811411PW_BS000058107313PW_BS00010710813PW_BS00010816212181PW_BS00016217018PW_BS000170188118PW_BS000024151141PW_BS0001512231241PW_BS0000242491341PW_BS000024171211PW_BS0000173183123PW_BS000024315123PW_BS0000241115121PW_BS000111350114121PW_BS00002834524121PW_BS0000281321121PW_BS00013213412121PW_BS000134253541PW_BS000024124151PW_BS0001243841251PW_BS000100388161PW_BS0001123911261PW_BS0001121181171PW_BS000118122551PW_BS0001224182451PW_BS00011512112171PW_BS00012143311451PW_BS0001151355171PW_BS00013545424171PW_BS000115468114171PW_BS0001152975101PW_BS00002448924101PW_BS0001152991101PW_BS000024205561PW_BS0000245062461PW_BS0001154311PW_BS0000043211PW_BS000003221411PW_BS000022592711PW_BS0000595411PW_BS00000529111PW_BS000029311511PW_BS000031111811PW_BS000011181311PW_BS000018101711PW_BS00001014101PW_BS000014541315PW_BS0000546131PW_BS0000061021231PW_BS0001021041431PW_BS000104103331PW_BS000103101531PW_BS0001011553241PW_BS0001551613181PW_BS00016111PW_BS0000011783211PW_BS0001781601181PW_BS00016019914181PW_BS0000241632181PW_BS0001631985181PW_BS00002421013181PW_BS000024222341PW_BS000024226441PW_BS000024224241PW_BS0000241951318PW_BS00002449711PW_BS00004929341PW_BS0000241333121PW_BS00013332914121PW_BS0000283344121PW_BS0000281122121PW_BS0001123361121PW_BS00002812915121PW_BS0001291151012PW_BS00011533217121PW_BS00002833527121PW_BS00002813013121PW_BS0001303331212PW_BS0000283317121PW_BS0000283683601PW_BS0000283744171PW_BS0000531192171PW_BS0001193761017PW_BS0000533821451PW_BS000100383751PW_BS0001002881441PW_BS0000243891461PW_BS000112390761PW_BS00011239914171PW_BS0001133987171PW_BS000113406351PW_BS000115405105PW_BS000115407251PW_BS000115117131PW_BS0001171231751PW_BS0001231251351PW_BS000125429151PW_BS000115408451PW_BS0001154141551PW_BS0001154222751PW_BS0001151203171PW_BS00012044717171PW_BS00011513613171PW_BS0001364641171PW_BS00011545015171PW_BS00011537527171PW_BS0000534793101PW_BS0001154781010PW_BS00011548012101PW_BS00011548414101PW_BS0001154812101PW_BS00011549127101PW_BS0001154824101PW_BS00011530013101PW_BS000024501361PW_BS000115209106PW_BS000024206261PW_BS0000245082761PW_BS000115502461PW_BS0001153951361PW_BS00011315111PW_BS000015261115PW_BS0000267028511PW_BS000070100521PW_BS000100105113PW_BS0001051471241PW_BS0001471572241PW_BS00015715924PW_BS00015916611PW_BS00016615284PW_BS0001521873118PW_BS000024219314PW_BS00002422014PW_BS0000242137181PW_BS00002421217181PW_BS0000242253541PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS0000242941141PW_BS0000243081011PW_BS0000243221231PW_BS0000243125231PW_BS0000243201123PW_BS0000241141112PW_BS00011432711125PW_BS00002834713125PW_BS000028310312PW_BS00002430412PW_BS000024943PW_BS000094109323PW_BS000109409115PW_BS0001154241155PW_BS0001154251355PW_BS0001151371117PW_BS00013745911175PW_BS00011546013175PW_BS0001154831110PW_BS0001154957101PW_BS000115208116PW_BS000024231511PW_BS00002312815121PW_BS0001284101551PW_BS00011544415171PW_BS00011548515101PW_BS0001153211515PW_BS000032892PW_BS0000892905491PW_BS00002430635511PW_BS000024372102PW_BS0000289611PW_BS00000913121PW_BS0000132811611PW_BS000028204111PW_BS000020331811PW_BS000033432511PW_BS0000432441011PW_BS00002460251PW_BS00006046114PW_BS00004672513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS0000971136121PW_BS000113110231PW_BS000110126651PW_BS00012612711651PW_BS000127140103PW_BS00014014315191PW_BS0001431465191PW_BS000146951721PW_BS0000951802211PW_BS000180207661PW_BS0000242111018PW_BS00002421425181PW_BS0000242156181PW_BS0000242164181PW_BS0000241901118PW_BS0000242771218PW_BS00002465111PW_BS0000652916491PW_BS0000242924491PW_BS00002429817101PW_BS0000243016101PW_BS000024302116101PW_BS000024337116121PW_BS00002834141121PW_BS00002834318121PW_BS0000283522512PW_BS00002835325127PW_BS00002835625121PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS0001154151851PW_BS0001154192551PW_BS00011543441051PW_BS000115436255PW_BS0001154436171PW_BS0001154461217PW_BS000115448116171PW_BS00011545118171PW_BS00011545525171PW_BS000115469410171PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS00011549025101PW_BS0001155041861PW_BS0001155072561PW_BS00011551541061PW_BS0001155131761PW_BS000115471914PW_BS000047241529PW_BS00002425715291PW_BS000024562611PW_BS00005614117191PW_BS000141244729PW_BS0000242481429PW_BS000024196718PW_BS00002481Glycerol 3-phosphateHMDB0000126Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia).17989-41-2C0009343916215978GLYCEROL-3P388308DB02515OC[C@@H](O)COP(O)(O)=OC3H9O6PInChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1AWUCVROLDVIAJX-GSVOUGTGSA-N[(2R)-2,3-dihydroxypropoxy]phosphonic acid172.0737172.013674532-0.7543-phosphoglycerol0-2FDB0218001-(dihydrogen phosphate) glycerol;1-glycerophosphate;1-glycerophosphorate;1-glycerophosphoric acid;3-glycerophosphate;Dl-glycerol 1-phosphate;Dl-glycerol 3-phosphate;Dl-a-glycerol phosphate;Dl-a-glycerophosphate;Dl-a-glycerophosphorate;Dl-a-glycerophosphoric acid;Dl-a-glyceryl phosphate;Dl-alpha-glycerol phosphate;Dl-alpha-glycerophosphate;Dl-alpha-glycerophosphorate;Dl-alpha-glycerophosphoric acid;Dl-alpha-glyceryl phosphate;Dihydrogen a-glycerophosphate;Glycerol 1-phosphate;Glycerol a-phosphate;Glycerol monophosphate;Glycerophosphate;Glycerophosphorate;Glycerophosphoric acid;Glycerophosphoric acid i;Glyceryl phosphate;Sn-gro-1-p;Sn-glycerol 3-phosphate;A-glycerophosphate;A-glycerophosphorate;A-glycerophosphoric acid;A-phosphoglycerol;Alpha-glycerophosphate;Alpha-glycerophosphorate;Alpha-glycerophosphoric acid;Alpha-phosphoglycerol;D-glycerol 1-phosphate;Glycerol 3-phosphoric acid;D-glycerol 1-phosphoric acidPW_C000081Glyc1P10438147521488422115586295107629610884121629122170106531881254615112550223153192493481417424663184246731578030111780523507837234578378132799521348180825393826124947893841105533881106363911158401181207561221212974181213451211214154331233531351238674541239744681257882971259784891259912991272432051274315061099Coenzyme 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_C001099CoA211438688453879228921724075924142245952813292862313342113351184618104629584842144865544879652321025247104528010354771245734108577710160231556075161638416468178693016069611626973199708318871081637293198734721074582228229151908122690902249124170921519513013299153182492548849426163157690729377119133772221347723032977292111775501327755533477563112776333367767212977996115780473327805635078413335785671307925933379974331800053688062011880627374806351198066537693828382938343839867428811055538911056139011584239911584739811995140612014740512023138412030512212063440712076211712140612312142143312152112512166642912168240812171441412240442212274112012290412112296013512396544712397946812407913612422046412426545012497437512534147912550947812557948012559248412563429712608448112654949112656048212674630012688450112704620912710939112730120512754020612766738812812150812813350212834039540034Hydrogen 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+21546708753157883184831116214632614645422314927801742502242544245471045761846947052411035327111535311256261085639107569910057201055742117596314760371556070157609316161301596232166648317866011526692101684318869101877100163716820571912067453219745422074722227525213753221075582127572160759017081952258218151824322684131628420224913919591552491191516412015281121812851224628612266287125212271325722313325294153303084232931542354318424013224240531242454320769122937713613377210134773723317780411477955132779903277799134778379345799291308001936880387310803883048072211993823124948233831105503881128559411328039011553739811553911811585633611620510911997340612019340712054912212059340912117042412117142512256941812261538412268712512275812012318313512321813712374245912374346012514145412518812112527313612535947912555048112573048312573629712580929912651749512671748912676648012682330012690250112721320812830850612836139112843039557Cytidine triphosphateHMDB0000082Cytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine.65-47-4C00063617617677CTP5941DB02431NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC9H16N3O14P3InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1PCDQPRRSZKQHHS-XVFCMESISA-N({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid483.1563482.984511771-1.647CTP0-3FDB0128335'-(tetrahydrogen triphosphate) cytidine;5'-ctp;Ctp;Cytidine 3'-triphosphate;Cytidine 5'-(tetrahydrogen triphosphate);Cytidine 5'-triphosphate;Cytidine 5'-triphosphoric acid;Cytidine 5-prime-triphosphate;Cytidine triphosphate;Cytidine mono;Cytidine mono(tetrahydrogen triphosphate) (ester);Cytidine-5'-triphosphate;Deoxycytosine triphosphate;H4ctpPW_C000057CTP42723115082718257661015800108707718875931609137195914221312194164125102881528515115317249153422215374183475917426503157731512878448111787331327994913479957130799643298041617094784384948121259481738298677223110633391113268395113273389115525136115530399120328410120854122121340121122212124122983444123434135124764118125654485125840297126374299127292205127935388170PyrophosphateHMDB0000250The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.14000-31-8C0001364410218361PPI559142DB04160[O-]P([O-])(=O)OP([O-])([O-])=OO7P2InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4XPPKVPWEQAFLFU-UHFFFAOYSA-J(phosphonooxy)phosphonic acid173.9433173.9119253784pyrophosphoric acid0-3FDB021918(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ionPW_C000170Ppi1223546384292373532882221217316204924105928152941751448685450348952521045294101540911754241035433118545812055481115559132558413356061355655108587910762391666978199707318871341637272160731219873182138275151828321011869161120022221204116412315225123232491251228812579226126952901521930615375183476017425613154269731877235329773171287763533678416335789283317915311279950134799581308004737280417170856301947863849481412594819382986782231106343911132703951132753891155271361155323991199341221200171241200324061203304101209364071212614291213411211214863831224074221229854441235021191238314641240443981249773751253242971253952991254104791255974841256564851258764811265524911268692051269353881269505011273372061281245081420WaterHMDB0002111Water 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_C001104Pi244848814581818831298031763141767492500102729472737463129293166723636613851234249224475315031275158752079752161005317111535111253811035447120554312955731335605135562510856936584814358551465911147594115160401556100161629410764871786691101671411768421886889160716120571892067212211730619873892107402212743616374752228196225825822710118241101342571174813211761115117732131190417011927164120142811272829013263223348191742255304423503154243531843692322770182537719429377217134779403367796613078048332780573297824535378669331800223688927930893831383947963841105583901106403911132359411584539811620610911998240612006912212069940712105712412121612512126842912135212112140912312142338212185240512330411912362111812378613612383846412396844712398139912440537612494847212536247912544629712577448112595429912622147812659430012660429812672348412690450112741338812778320912816639512817751312831538964Cytidine monophosphateHMDB0000095Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991].63-37-6C00055613117361CMP5901NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1OC9H14N3O8PInChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1IERHLVCPSMICTF-XVFCMESISA-N{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid323.1965323.051850951-1.305cytidine monophosphate0-2FDB0118825'-cmp;5-cytidylate;5-cytidylic acid;Cmp;Cytidine 5'-monophosphate;Cytidine 5'-monophosphorate;Cytidine 5'-monophosphoric acid;Cytidine 5'-phosphate;Cytidine 5'-phosphorate;Cytidine 5'-phosphoric acid;Cytidine mono(dihydrogen phosphate);Cytidine monophosphate;Cytidylate;Cytidylic acid;Cytidine-5'-monophosphate;Pc;Cytidine-5'-monophosphoric acidPW_C000064CMP11518251214273423386184972565768101580210870791887595160914724991512249257195121961641221015115274285153363081537349348151742652315784491117848811578573130787361327995313479969331804211709479138494821383986802231106373911132773901155353981208551221213461211222161241224874051226051251234351351247681181250533761251771361258412971263782991266414781267523001272932051279403881282172091283463951134Dihydroxyacetone 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_C001134Dhapp10268147423305542534258131085908147593615168841604266031577098132779341117837434578559334938241241105513881158391181207331221225644181225904081233331351251374541251623741257872971259502991267124891267364821272422051283035061283305021144NADHHMDB0001487NADH 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_C001144NADH14341533490864810111521275514695422304927811728362931099480618481218482128490464959315169955240103533211153581125466123547912555931355698100573710858291415915147594515160271556079161638716472178677111768931607011188709916371722057195206746222282442268360225908622411809198118212161232024913003298130153001325522342403322426183157710713277123133772081347737133177651336776683347770033277707130779171137798634780009368806911199382212411054938811285494115838118119955406120172407120378122120986408121162425121244126121693429121818383122616384122745120123127447123138136123551374123734460123814443124242464124371398125189121125345479125531481125762297125808299125926482126516495126767480126888501127385502128090390128362391128429395721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium664.433664.116946663-2.5981-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-1FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nadPW_C000721NAD14041503353865110111421134431273514665422294927791728352931079480718481318481928490264960315167955238103533411153601125469123548212555901355610118569610057381085827141591214759421516024155607215760761616385164691786772117689016070121887097163717420571972067405198745922282412268359225908522411819216123222491300629813018300132562234240432242619315771041327712013377209134773703317765033677667334777023327770913077915113779833477840635680006368806901199382512411055238811275016611285394119929122119952406120171407120834419120984408121159425121242126121259429121817383122614384122742120123130447123141136123419455123549374123731460123812443123829464124370398125187121125319297125342479125530481125806299125825490125924482126515495126765480126885501127278507127383502128089390128360391128428395210Long-chain fatty acyl-CoA Compound1031CompoundPW_EC000210LCFAC1371-Acyl-sn-glycerol 3-phosphate Compound42911CompoundPW_EC0001371ASG3P2301,2-Diacyl-sn-glycerol 3-phosphateCompound3906CompoundPW_EC0002301,2DG3P142a CDP-diacylglycerol Compound3023CompoundPW_EC000142ACD158an L-1-phosphatidylglycerol-phosphate Compound8452CompoundPW_EC000158AL1PP156an L-1-phosphatidyl-glycerol CompoundCompoundPW_EC000156AL1PG141a CardiolipinCompound6699CompoundPW_EC000141CL3971-MonolysocardiolipinCompound44796CompoundPW_EC00039765106ChEBI1M25Fatty AcidCompound145CompoundPW_EC00002535366ChEBIFA74PhosphatidylcholineCompound440CompoundPW_EC00007464482ChEBIPhospha292LysoPCCompound6391CompoundPW_EC000292LysoPC10720Maintenance of mitochondrial morphology protein 1P41800Component of the ERMES/MDM complex, which serves as a molecular tether to connect the endoplasmic reticulum and mitochondria. Components of this complex are involved in the control of mitochondrial shape and protein biogenesis and may function in phospholipid exchange. The MDM12-MMM1 subcomplex functions in the major beta-barrel assembly pathway that is responsible for biogenesis of all outer membrane beta-barrel proteins, and acts in a late step after the SAM complex. The MDM10-MDM12-MMM1 subcomplex further acts in the TOM40-specific pathway after the action of the MDM12-MMM1 complex. Essential for establishing and maintaining the structure of mitochondria and maintenance of mtDNA nucleoids.MMM129899724410721Mitochondrial distribution and morphology protein 12Q92328Display
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Functioni
Component of the ERMES/MDM complex, which serves as a molecular tether to connect the endoplasmic reticulum and mitochondria. Components of this complex are involved in the control of mitochondrial shape and protein biogenesis and may function in phospholipid exchange. MDM12 is required for the interaction of the ER-resident membrane protein MMM1 and the outer mitochondrial membrane-resident beta-barrel protein MDM10. The MDM12-MMM1 subcomplex functions in the major beta-barrel assembly pathway that is responsible for biogenesis of all mitochondrial outer membrane beta-barrel proteins, and acts in a late step after the SAM complex. The MDM10-MDM12-MMM1 subcomplex further acts in the TOM40-specific pathway after the action of the MDM12-MMM1 complex. Essential for establishing and maintaining the structure of mitochondria and maintenance of mtDNA nucleoids.MDM122910722Mitochondrial distribution and morphology protein 10P18409Component of the ERMES/MDM complex, which serves as a molecular tether to connect the endoplasmic reticulum and mitochondria. Components of this complex are involved in the control of mitochondrial shape and protein biogenesis and may function in phospholipid exchange. MDM10 is involved in the late assembly steps of the general translocase of the mitochondrial outer membrane (TOM complex). Functions in the TOM40-specific route of the assembly of outer membrane beta-barrel proteins, including the association of TOM40 with the receptor TOM22 and small TOM proteins. Can associate with the SAM(core) complex as well as the MDM12-MMM1 complex, both involved in late steps of the major beta-barrel assembly pathway, that is responsible for biogenesis of all outer membrane beta-barrel proteins. May act as a switch that shuttles between both complexes and channels precursor proteins into the TOM40-specific pathway. Plays a role in mitochondrial morphology and in the inheritance of mitochondria.MDM1029899824810723Mitochondrial distribution and morphology protein 34P53083Component of the ERMES/MDM complex, which serves as a molecular tether to connect the endoplasmic reticulum and mitochondria. Components of this complex are involved in the control of mitochondrial shape and protein biogenesis and may function in phospholipid exchange. MDM34 is required for the interaction of the ER-resident membrane protein MMM1 and the outer mitochondrial membrane-resident beta-barrel protein MDM10.MDM3429899924810724Protein UPS1, mitochondrialQ05776Required for maintenance of normal mitochondrial morphology as well as PCP1-dependent processing of MGM1. With UPS2, controls the level of cardiolipin in mitochondria. Cardiolipin is a unique phospholipid with four fatty acid chains and is present mainly in the mitochondrial inner membrane where it stabilizes the electron transport chain supercomplex between complexes III and IV through direct interaction of their subunits.UPS12910725Mitochondrial distribution and morphology protein 35O60200Involved in mitochondrial distribution and morphology. Mediates the import of UPS1, UPS2 and UPS3, 3 atypical mitochondrial intermembrane space (IMS) proteins lacking the two major IMS-targeting signals, into the intermembrane space.MDM352910942Glycerol-3-phosphate dehydrogenaseQ00055
Catalyzes the production and accumulation of glycerol during hyperosmotic stress conditions. Glycerol acts as a osmoregulator that prevents loss of water and turgor of the cells.
GPD1291.1.1.8780521013817816313818919810943Glycerol-3-phosphate dehydrogenase GPD2P41911
Catalyzes the production of glycerol under anaerobic growth conditions. Glycerol production serves as a redox sink by consuming the excess cytosolic NADH during anaerobic metabolism.
GPD2,GPD3291.1.1.8780421013817916313819019810658Glycerol-3-phosphate O-acyltransferase 2P36148
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase.
GTP2292.3.1.15; 2.3.1.4276801607687213780221091261701065418813818019610659Glycerol-3-phosphate O-acyltransferase 1P32784
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase.
SCT1292.3.1.15; 2.3.1.4276791607686213780321091271701065518813818119610661Acyl-CoA:lyso-phospholipid acyltransferaseQ08548
Membrane-bound O-acyltransferase that mediates the incorporation of unsaturated acyl chains into the sn-2 position of phospholipids. Preferentially acylates lysophosphocholine, but also lysophosphoethanolamine and lysophosphatidylglycerol.
ALE1292.3.1.23; 2.3.1.5176831607688213779821091311888040517013818219610662Lipase 4P36165
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation.
TGL4293.1.1.376851607692213779921091321888040617013818319610663Probable 1-acyl-sn-glycerol-3-phosphate acyltransferaseP33333
May be an acyltransferase with an altered substrate specificity that enables it to use a C-26-CoA in place of the C-16 or C-18-CoAs used by the wild-type protein.
SLC1292.3.1.5176821607689213780021091331888040717013818419610664Lipase 5Q12043
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation.
TGL5293.1.1.376841607691213779721091341888040817013818519610665Lysophosphatidic acid:oleoyl-CoA acyltransferase 1Q06508
Acyl-CoA-dependent lysophosphatidic acid acyltransferase with preference for oleoyl-CoA. Involved in triacylglyceride homeostasis and lipid droplet formation. Involved in vacuolar protein sorting.
LOA1292.3.1.5176811607690213779621091351888040917013818619610726Phosphatidate cytidylyltransferaseP38221
Supplies CDP-diacylglycerol, which may play an important role as both a precursor to phosphoinositide biosynthesis in the plasma membrane and as a negative effector of phosphatidylinositol 4-kinase activity, thereby exerting an effect on cell proliferation via a lipid-dependent signal transduction cascade.
CDS1292.7.7.4176941638041817013819716210727Phosphatidate cytidylyltransferase, mitochondrialP53230
Catalyzes the formation of CDP-diacylglycerol (CDP-DAG) from phosphatidic acid (PA) in the mitochondrial inner membrane. Required for the biosynthesis of the dimeric phospholipid cardiolipin, which stabilizes supercomplexes of the mitochondrial respiratory chain in the mitochondrial inner membrane.
TAM41292.7.7.417693163804191708043216210729Phosphatidylglycerophosphatase GEP4, mitochondrialP38812
Phosphatidylglycerophosphatase involved in the biosynthesis of cardiolipin (CL), a unique dimeric phosphoglycerolipid predominantly present in mitochondrial membranes and which has important functions for cellular energy metabolism, mitochondrial dynamics and the initiation of apoptotic pathways. Required for the stability of respiratory chain supercomplexes and for growth at elevated temperature, in presence of ethidium bromide or in absence of prohibitins.
GEP4293.1.3.277696160769816313819816210728CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferaseP25578
Essential for the viability of mitochondrial petite mutant. Catalyzes the committed step to the synthesis of the acidic phospholipids.
PGS1292.7.8.5769516076971638043316210730Cardiolipin synthase (CMP-forming)Q07560
Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) by specifically transferring a phosphatidyl group from CDP-diacylglycerol to phosphatidylglycerol (PG). CL is a key phospholipid in mitochondrial membranes and plays important roles in maintaining the functional integrity and dynamics of mitochondria under both optimal and stress conditions.
CRD1292.7.8.41769916313819916223176Cardiolipin-specific deacylase 1, mitochondrialP53264
Mitochondrial cardiolipin-specific phospholipase which deacylates de novo synthesized cardiolipin. Part of the remodeling process of cardiolipin, which involves deacylation-reacylation of premature cardiolipin. Has a strong substrate preference for palmitic acid residues and generates monolysocardiolipin for TAZ1-dependent reacylation with unsaturated fatty acids.
CLD1293.5.1.-13820016211304Lysophosphatidylcholine acyltransferaseQ06510Acyltransferase which mediates the conversion of 1-acyl-sn-glycero-3-phosphocholine (LPC) into phosphatidylcholine (PC). Displays a broad LPC fatty acyl chain substrate specificity utilizing LPC molecules ranging in length from C-10 to C-20. Does not utilize other lysolipids than LPC as acceptor. Also shows acyl-CoA-independent acyltransferase activity. Required for normal phospholipid content of mitochondrial membranes. Involved in the remodeling of the acyl groups of cardiolipin in the mitochondrial inner membrane, which affects the assembly and stability of respiratory chain complex IV and its supercomplex forms.TAZ1292.3.1.2392221631382011624392ERMES COMPLEX18PW_P00439211472107201147310721114741072211475107234393Ups1/Mdm35p heterodimer18PW_P004393114761072411477107254720Glycerol-3-phosphate dehydrogenase18PW_P004720119021094211903109434341Glycerol-3-phosphate O-acyltransferase 18PW_P004341114041065811405106594343Lysophosphatidate acyltransferase18PW_P004343114071066111408106621140910663114101066411411106654394Phosphatidate cytidylyltransferase18PW_P004394114781072611479107274396Phosphatidylglycerophosphatase GEP4, mitochondrial18PW_P00439611481107294395CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase18PW_P00439511480107284397Cardiolipin synthase (CMP-forming)18PW_P004397114821073013896Ccardiolipin-specific phospholipase18PW_P01389623813231765054Lysophosphatidylcholine acyltransferase18PW_P0050541234611304187406PW_R187406Both71004111341Compoundfalse71004211441Compoundfalse710043400341Compoundfalse710044811Compoundfalse7100457211Compoundfalse1770654720110842PW_R110842Right4032712101ElementCollectionfalse403272811Compoundfalse40327310991Compoundfalse4032741371ElementCollectionfalse1011364341110843PW_R110843Right4032751371ElementCollectionfalse4032762101ElementCollectionfalse4032772301ElementCollectionfalse40327810991Compoundfalse10113743432.3.1.23,2.3.1.51110846PW_R110846Right4032852301ElementCollectionfalse403286571Compoundfalse403287400341Compoundfalse4032881701Compoundfalse4032891421ElementCollectionfalse1011384394110848PW_R110848Right4032951581ElementCollectionfalse40329614201Compoundfalse4032971561ElementCollectionfalse40329811041Compoundfalse1011404396110847PW_R110847Right4032901421ElementCollectionfalse403292811Compoundfalse4032911581ElementCollectionfalse403293400341Compoundfalse403294641Compoundfalse1011394395110849PW_R110849Right4032991561ElementCollectionfalse4033001421ElementCollectionfalse4033011411ElementCollectionfalse403302641Compoundfalse403303400341Compoundfalse1011414397187416PW_R187416Right7100871411ElementCollectionfalse71009014201Compoundfalse7100883971ElementCollectionfalse710089251ElementCollectionfalse177072138963.5.1.-187417PW_R187417Right7100913971ElementCollectionfalse710094741ElementCollectionfalse7100921411ElementCollectionfalse7100932921ElementCollectionfalse17707350541167PW_T00116614102301ElementCollection210199Right98643922018-07-16T14:54:46-06:002018-07-16T14:54:46-06:001701168PW_T00116814112301ElementCollection199162Right98743932018-07-16T14:58:50-06:002018-07-16T14:58:50-06:0017078678812133false70134710regular10011078681109921385false106630210regular503078684109921385false109870710regular5030786894003416255false1420139810regular787878690571623false1398148710regular1001107869117016245false1436172510regular634378697142016249false1276220410regular787878698110416246false1068224010regular444378701641623false550216910regular100110787024003416255false676220410regular78781588753811623false1401190610regular10011015887544003416255false1423209710regular78781588755641623false1406219610regular100110275780111341983false30134510regular1001102757802114419860false40630010regular503027578034003419855false37247510regular7878275780472119859false65130210regular50302757833142016249false552193510regular7878966821037213false75148212regular10090966913737213false113134212regular10090967021037213false124142212regular10090967723037213false113375712regular10090967823037199false1133111212regular10090967923037162false1523126712regular10090968114237162false1521179612regular10090968215837162false1521230612regular10090968315637162false975231012regular10090968414237162false900217012regular10090968514137162false420231912regular10090968814137162false900127912regular100902301139737162false420165412regular10090230122537162false550176412regular10090230137437162false580139912regular100902301429237162false825139912regular100905950801072076false10539128subunitregular150705950811072176false11589128subunitregular150705950821072276false11589628subunitregular150705950831072376false10539628subunitregular150705950911072476false1158129219subunitregular150705950921072576false105812928subunitregular15070980542109421982true5763928subunitregular15070980543109431982false4763678subunitregular15070980545106582132false8864148subunitregular15070980546106592132false8863698subunitregular15070980547106612132false11065378subunitregular15070980548106622132false11965527subunitregular15070980549106632132false11065728subunitregular15070980550106642132false11965927subunitregular15070980551106652132false11066078subunitregular15070980553107261622true166316018subunitregular15070980554107271622false149816018subunitregular15070980555107291622false113023358subunitregular15070980556107281622false149620238subunitregular15070980557107301622false75023348subunitregular15070980598231761622false39518668subunitregular15070980599113041622false67712918subunitregular15070483034439221885936385950805936395950815936405950825936415950834830364393218859364759509159364859509282984647202188198976272980542976273980543829848434121882139762759805459762769805468298494343218821397627798054797627898054897627998054997628098055097628198055182985143942188162976283980553976284980554829852439621881629762859805558298534395218816297628698055682985443972188162976287980557829875138962188162976328980598829876505421881629763299805992166269M1183 877 C1183 907 1183 883 1183 913 83false18trueM 2074.5 1624.0096189432334 L 2082 1637 L 2089.5 1624.0096189432334false2166270M1183 1112 C1182 1093 1183 1059 1183 1032 83false18trueM 1582.9468550441647 1270.261556296296 L 1568 1269 L 1574.380887721186 1282.5751343230784false2166275M1183 1232 C1183 1269 1183 1261 1184 1288 83false18trueM 2343.0465069166444 2037.5045463730214 L 2357 2032 L 2345.256176462976 2022.6681937047942false2166276M1523 1327 C1445 1326 1243 1328 1208 1327 83false18trueM 1441.9468550441647 1482.261556296296 L 1427 1481 L 1433.380887721186 1494.5751343230784false3779381M401 400 C431 400 446 402 476 402 5false18trueM 308.94685504416486 297.261556296296 L 294 296 L 300.38088772118584 309.5751343230783false3779382M431 330 C429 377 446 402 476 402 5false18trueM 308.94685504416486 297.261556296296 L 294 296 L 300.38088772118584 309.5751343230783false3779383M411 475 C410 437 446 402 476 402 5false18trueM 308.94685504416486 297.261556296296 L 294 296 L 300.38088772118584 309.5751343230783false3779384M701 402 C671 402 656 402 626 402 5false18trueM 308.94685504416486 297.261556296296 L 294 296 L 300.38088772118584 309.5751343230783false3779385M676 332 C675 381 651 402 626 402 5false18trueM 308.94685504416486 297.261556296296 L 294 296 L 300.38088772118584 309.5751343230783false3779388M801 402 C831 402 856 404 886 404 5false183779389M1091 332 C1092 367 1066 404 1036 404 5false18trueM 476.94685504416486 329.261556296296 L 462 328 L 468.38088772118584 341.5751343230783false3779390M801 482 C809 421 856 404 886 404 5false183779391M1131 402 C1101 402 1066 404 1036 404 5false18trueM 476.94685504416486 329.261556296296 L 462 328 L 468.38088772118584 341.5751343230783false3779392M1148 722 C1183 716 1181 707 1181 677 5false18trueM 715.9468550441649 393.261556296296 L 701 392 L 707.3808877211858 405.5751343230783false3779393M1181 462 C1181 492 1181 507 1181 537 5false183779394M1241 477 C1201 472 1181 507 1181 537 5false183779395M1183 757 C1183 727 1181 707 1181 677 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