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KEGG COMPOUND: C00036
<!doctype html> <html><head> <title>KEGG COMPOUND: C00036</title> <link type="text/css" rel="stylesheet" href="/css/gn2.css?1742029028"> <link type="text/css" rel="stylesheet" href="/css/bget.css?1742029028"> <meta name="viewport" content="width=device-width, initial-scale=1.0"> <link type="text/css" rel="stylesheet" href="/css/bgetm.css?1742029028" media="only screen and (max-width: 768px)"> <style>.kcfd{display:none;}</style> <script> <!-- var getElementsByClassName = document.getElementsByClassName ? function (cl){ return document.getElementsByClassName(cl); } : function (cl){ var elms = []; var objs = document.getElementsByTagName('*'); for(var i=0;i<objs.length;i++){ var obj = objs[i]; if(obj.className == cl){ elms.push(obj); } } return elms; }; function toggleField(clk,cl,show,hide){ var objs = getElementsByClassName(cl); for(var i=0;i<objs.length;i++){ var obj = objs[i]; if(!obj.style.display||obj.style.display == 'none'){ obj.style.display = 'block'; clk.innerHTML = ' « '+hide; 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form.setAttribute(key,params[key]); } else{ var obj = document.createElement('input'); obj.setAttribute('type','hidden'); obj.setAttribute('name',key); obj.setAttribute('value',params[key]); form.appendChild(obj); } } form.submit(); } window.onload=function(){window.focus();init();}; //---> </script> </head> <body> <div> <table border=0 cellpadding=0 cellspacing=0><tr><td> <table border=0 cellpadding=0 cellspacing=0 width="650"><tr><td width=70><a href="/kegg/kegg2.html"><img align="middle" alt="KEGG" border=0 src="/Fig/bget/kegg2.gif"></a></td><td> </td><td><a name="compound:C00036"></a><font class="title2">COMPOUND: C00036</font></td><td class="tar vbot"><button class="btn" onclick="javascript:void(window.open('/kegg/document/help_bget_compound.html','KEGG_Help','toolbar=no,location=no,directories=no,width=720,height=640,resizable=yes,scrollbars=yes'));return false;">Help</button></td></tr></table><form method="post" action="/entry/" enctype="application/x-www-form-urlencoded" id="form1" name="form1"></form><table class="w1" width="650"> <tr> <td class="fr2 w1"> <table width="650" class="w2"> <tr><th class="th20 deft tal vmid"><span class="nowrap">Entry</span></th> <td class="td20 defd"><table class="w1" width="100%"><tr><td class="tal pd0"><code><span class="nowrap">C00036 Compound <br> </span></code></td></tr></table></td></tr> <tr><th class="th21 deft tal vtop"><span class="nowrap">Name</span></th> <td class="td21 defd"><div class="cel"><div class="cel">Oxaloacetate;<br> Oxalacetic acid;<br> Oxaloacetic acid;<br> 2-Oxobutanedioic acid;<br> 2-Oxosuccinic acid;<br> keto-Oxaloacetate<br> </div></div></td></tr> <tr><th class="th20 deft tal vtop"><span class="nowrap">Formula</span></th> <td class="td20 defd"><div class="cel">C4H4O5<br> </div></td></tr> <tr><th class="th21 deft tal vtop"><span class="nowrap">Exact mass</span></th> <td class="td21 defd"><div class="cel">132.0059<br> </div></td></tr> <tr><th class="th20 deft tal vtop"><span class="nowrap">Mol weight</span></th> <td class="td20 defd"><div class="cel">132.07<br> </div></td></tr> <tr><th class="th21 deft tal vtop"><span class="nowrap">Structure</span></th> <td class="td21 defd"><a href="/Fig/compound/C00036.gif"><img name="img0" src="/Fig/compound/C00036.gif" style="max-width:600px" border=0></a><br> <button class="btn" onclick="location.href='/entry/-f+m+C00036';return false;">Mol file</button><button class="btn" onclick="location.href='/entry/-f+k+C00036';return false;">KCF file</button><button class="btn" onclick="location.href='https://www.genome.jp/tools-bin/strsearch_view?ENTRY=C00036&PROGRAM=simcomp&DATABASE=compound';return false;">DB search</button></td></tr> <tr><th class="th20 deft tal vtop"><span class="nowrap">Reaction</span></th> <td class="td20 defd"><div class="cel"><a href="/entry/R00217">R00217</a> <a href="/entry/R00338">R00338</a> <a href="/entry/R00339">R00339</a> <a href="/entry/R00340">R00340</a> <a href="/entry/R00341">R00341</a> <a href="/entry/R00342">R00342</a> <a href="/entry/R00343">R00343</a> <a href="/entry/R00344">R00344</a> <br> <a href="/entry/R00345">R00345</a> <a href="/entry/R00346">R00346</a> <a href="/entry/R00347">R00347</a> <a href="/entry/R00348">R00348</a> <a href="/entry/R00350">R00350</a> <a href="/entry/R00351">R00351</a> <a href="/entry/R00352">R00352</a> <a href="/entry/R00353">R00353</a> <br> <a href="/entry/R00354">R00354</a> <a href="/entry/R00355">R00355</a> <a href="/entry/R00357">R00357</a> <a href="/entry/R00359">R00359</a> <a href="/entry/R00360">R00360</a> <a href="/entry/R00361">R00361</a> <a href="/entry/R00362">R00362</a> <a href="/entry/R00363">R00363</a> <br> <a href="/entry/R00373">R00373</a> <a href="/entry/R00400">R00400</a> <a href="/entry/R00431">R00431</a> <a href="/entry/R00477">R00477</a> <a href="/entry/R00493">R00493</a> <a href="/entry/R00695">R00695</a> <a href="/entry/R00726">R00726</a> <a href="/entry/R00930">R00930</a> <br> <a href="/entry/R00931">R00931</a> <a href="/entry/R01144">R01144</a> <a href="/entry/R01257">R01257</a> <a href="/entry/R01447">R01447</a> <a href="/entry/R01713">R01713</a> <a href="/entry/R01731">R01731</a> <a href="/entry/R03735">R03735</a> <a href="/entry/R05053">R05053</a> <br> <a href="/entry/R05758">R05758</a> <a href="/entry/R07164">R07164</a> <a href="/entry/R07165">R07165</a> <a href="/entry/R09683">R09683</a> <a href="/entry/R12212">R12212</a> <a href="/entry/R13023">R13023</a> <a href="/entry/R13076">R13076</a> <a href="/entry/R13206">R13206</a> <br> <a href="/entry/R13207">R13207</a> <a href="/entry/R13222">R13222</a> <a href="/entry/R13306">R13306</a><br> </div></td></tr> <tr><th class="th21 deft tal vtop"><span class="nowrap">Pathway</span></th> <td class="td21 defd"><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00010+C00036">map00010</a> </span></td><td>Glycolysis / Gluconeogenesis</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00020+C00036">map00020</a> </span></td><td>Citrate cycle (TCA cycle)</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00250+C00036">map00250</a> </span></td><td>Alanine, aspartate and glutamate metabolism</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00362+C00036">map00362</a> </span></td><td>Benzoate degradation</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00470+C00036">map00470</a> </span></td><td>D-Amino acid metabolism</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00620+C00036">map00620</a> </span></td><td>Pyruvate metabolism</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00630+C00036">map00630</a> </span></td><td>Glyoxylate and dicarboxylate metabolism</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00640+C00036">map00640</a> </span></td><td>Propanoate metabolism</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00680+C00036">map00680</a> </span></td><td>Methane metabolism</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00710+C00036">map00710</a> </span></td><td>Carbon fixation by Calvin cycle</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00720+C00036">map00720</a> </span></td><td>Other carbon fixation pathways</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00946+C00036">map00946</a> </span></td><td>Degradation of flavonoids</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00997+C00036">map00997</a> </span></td><td>Biosynthesis of various other secondary metabolites</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00998+C00036">map00998</a> </span></td><td>Biosynthesis of various antibiotics</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map00999+C00036">map00999</a> </span></td><td>Biosynthesis of various plant secondary metabolites</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01060+C00036">map01060</a> </span></td><td>Biosynthesis of plant secondary metabolites</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01061+C00036">map01061</a> </span></td><td>Biosynthesis of phenylpropanoids</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01062+C00036">map01062</a> </span></td><td>Biosynthesis of terpenoids and steroids</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01063+C00036">map01063</a> </span></td><td>Biosynthesis of alkaloids derived from shikimate pathway</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01064+C00036">map01064</a> </span></td><td>Biosynthesis of alkaloids derived from ornithine, lysine and nicotinic acid</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01065+C00036">map01065</a> </span></td><td>Biosynthesis of alkaloids derived from histidine and purine</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01066+C00036">map01066</a> </span></td><td>Biosynthesis of alkaloids derived from terpenoid and polyketide</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01070+C00036">map01070</a> </span></td><td>Biosynthesis of plant hormones</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01100+C00036">map01100</a> </span></td><td>Metabolic pathways</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01110+C00036">map01110</a> </span></td><td>Biosynthesis of secondary metabolites</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01120+C00036">map01120</a> </span></td><td>Microbial metabolism in diverse environments</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01200+C00036">map01200</a> </span></td><td>Carbon metabolism</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01210+C00036">map01210</a> </span></td><td>2-Oxocarboxylic acid metabolism</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01230+C00036">map01230</a> </span></td><td>Biosynthesis of amino acids</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map01240+C00036">map01240</a> </span></td><td>Biosynthesis of cofactors</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map02020+C00036">map02020</a> </span></td><td>Two-component system</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map04922+C00036">map04922</a> </span></td><td>Glucagon signaling pathway</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map04964+C00036">map04964</a> </span></td><td>Proximal tubule bicarbonate reclamation</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/pathway/map05230+C00036">map05230</a> </span></td><td>Central carbon metabolism in cancer</td></tr></table></td></tr> <tr><th class="th20 deft tal vtop"><span class="nowrap">Module</span></th> <td class="td20 defd"><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00003+C00036">M00003</a> </span></td><td>Gluconeogenesis, oxaloacetate => fructose-6P</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00009+C00036">M00009</a> </span></td><td>Citrate cycle (TCA cycle, Krebs cycle)</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00010+C00036">M00010</a> </span></td><td>Citrate cycle, first carbon oxidation, oxaloacetate => 2-oxoglutarate</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00011+C00036">M00011</a> </span></td><td>Citrate cycle, second carbon oxidation, 2-oxoglutarate => oxaloacetate</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00012+C00036">M00012</a> </span></td><td>Glyoxylate cycle</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00168+C00036">M00168</a> </span></td><td>CAM (Crassulacean acid metabolism), dark</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00170+C00036">M00170</a> </span></td><td>C4-dicarboxylic acid cycle, phosphoenolpyruvate carboxykinase type</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00171+C00036">M00171</a> </span></td><td>C4-dicarboxylic acid cycle, NAD - malic enzyme type</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00172+C00036">M00172</a> </span></td><td>C4-dicarboxylic acid cycle, NADP - malic enzyme type</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00173+C00036">M00173</a> </span></td><td>Reductive citrate cycle (Arnon-Buchanan cycle)</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00346+C00036">M00346</a> </span></td><td>Formaldehyde assimilation, serine pathway</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00374+C00036">M00374</a> </span></td><td>Dicarboxylate-hydroxybutyrate cycle</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00620+C00036">M00620</a> </span></td><td>Incomplete reductive citrate cycle, acetyl-CoA => oxoglutarate</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00740+C00036">M00740</a> </span></td><td>Methylaspartate cycle</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap"><a href="/module/M00982+C00036">M00982</a> </span></td><td>Methylcitrate cycle</td></tr></table></td></tr> <tr><th class="th21 deft tal vtop"><span class="nowrap">Network</span></th> <td class="td21 defd"><div class="cel"><a href="/network/nt06031+C00036">nt06031</a> Citrate cycle and pyruvate metabolism</div></td></tr> <tr><th class="th20 deft tal vtop"><span class="nowrap">Enzyme</span></th> <td class="td20 defd"><div class="cel"><a href="/entry/1.1.1.37">1.1.1.37</a> <a href="/entry/1.1.1.38">1.1.1.38</a> <a href="/entry/1.1.1.40">1.1.1.40</a> <a href="/entry/1.1.1.82">1.1.1.82</a> <br> <a href="/entry/1.1.1.299">1.1.1.299</a> <a href="/entry/1.1.5.4">1.1.5.4</a> <a href="/entry/1.1.99.7">1.1.99.7</a> <a href="/entry/1.4.1.21">1.4.1.21</a> <br> <a href="/entry/1.4.3.1">1.4.3.1</a> <a href="/entry/1.4.3.2">1.4.3.2</a> <a href="/entry/1.4.3.15">1.4.3.15</a> <a href="/entry/1.4.3.16">1.4.3.16</a> <br> <a href="/entry/2.1.3.1">2.1.3.1</a> <a href="/entry/2.3.3.1">2.3.3.1</a> <a href="/entry/2.3.3.2">2.3.3.2</a> <a href="/entry/2.3.3.3">2.3.3.3</a> <br> <a href="/entry/2.3.3.5">2.3.3.5</a> <a href="/entry/2.3.3.8">2.3.3.8</a> <a href="/entry/2.3.3.16">2.3.3.16</a> <a href="/entry/2.6.1.1">2.6.1.1</a> <br> <a href="/entry/2.6.1.12">2.6.1.12</a> <a href="/entry/2.6.1.21">2.6.1.21</a> <a href="/entry/2.6.1.31">2.6.1.31</a> <a href="/entry/2.6.1.35">2.6.1.35</a> <br> <a href="/entry/2.6.1.57">2.6.1.57</a> <a href="/entry/2.6.1.70">2.6.1.70</a> <a href="/entry/2.6.1.78">2.6.1.78</a> <a href="/entry/2.6.1.126">2.6.1.126</a> <br> 2.6.1.- <a href="/entry/3.1.1.44">3.1.1.44</a> <a href="/entry/3.5.1.3">3.5.1.3</a> <a href="/entry/3.7.1.1">3.7.1.1</a> <br> <a href="/entry/4.1.1.31">4.1.1.31</a> <a href="/entry/4.1.1.32">4.1.1.32</a> <a href="/entry/4.1.1.38">4.1.1.38</a> <a href="/entry/4.1.1.49">4.1.1.49</a> <br> <a href="/entry/4.1.1.112">4.1.1.112</a> <a href="/entry/4.1.3.6">4.1.3.6</a> <a href="/entry/4.1.3.13">4.1.3.13</a> <a href="/entry/4.1.3.17">4.1.3.17</a> <br> <style>.e1{display:none;}</style><div class="e1"><a href="/entry/4.1.3.34">4.1.3.34</a> <a href="/entry/4.2.1.32">4.2.1.32</a> <a href="/entry/4.2.1.81">4.2.1.81</a> <a href="/entry/4.3.1.16">4.3.1.16</a> <br> <a href="/entry/4.3.1.20">4.3.1.20</a> <a href="/entry/4.3.1.27">4.3.1.27</a> <a href="/entry/5.3.2.2">5.3.2.2</a> <a href="/entry/6.4.1.1">6.4.1.1</a> <br> <a href="/entry/7.2.4.2">7.2.4.2</a><br> </div><a href="javascript:void(0)" onclick="javascript:toggleField(this,"e1","show all","hide")"> » show all</a><br> </div></td></tr> <tr><th class="th21 deft tal vtop"><span class="nowrap">Brite</span></th> <td class="td21 defd"><div class="cel"><span class="nowrap">Compounds with biological roles [BR:<a href="/brite/br08001+C00036">br08001</a>]<br> Organic acids<br> Carboxylic acids<br> 2-Oxocarboxylic acids<br> C00036 Oxaloacetate; 2-Oxosuccinate<br> Lipids [BR:<a href="/brite/br08002+C00036">br08002</a>]<br> FA Fatty acyls<br> FA01 Fatty Acids and Conjugates<br> FA0117 Dicarboxylic acids<br> C00036 2-Oxobutanedioic acid<br> </span></div><button class="btn" onclick="location.href='/kegg-bin/search_brite?option=-a&search_string=C00036';return false;">BRITE hierarchy</button></td></tr> <tr><th class="th20 deft tal vtop"><span class="nowrap">Other DBs</span></th> <td class="td20 defd"><table class="w1"><tr><td class="vtop pd0"><span class="nowrap">CAS: </span></td><td>328-42-7</td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap">PubChem: </span></td><td><a href="https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3338">3338</a></td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap">ChEBI: </span></td><td><a href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16452">16452</a> <a href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30744">30744</a></td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap">LIPIDMAPS: </span></td><td><a href="http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMFA01170120">LMFA01170120</a></td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap">KNApSAcK: </span></td><td><a href="http://kanaya.naist.jp/knapsack_jsp/information.jsp?sname=C_ID&word=C00001197">C00001197</a></td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap">PDB-CCD: </span></td><td><a href="https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/OAA">OAA</a>[<a href="https://pdbj.org/mine/summary/OAA">PDBj</a>] </td></tr></table><table class="w1"><tr><td class="vtop pd0"><span class="nowrap">NIKKAJI: </span></td><td><a href="https://jglobal.jst.go.jp/en/redirect?Nikkaji_No=J5.675H">J5.675H</a></td></tr></table></td></tr> <tr><th class="th21 deft tal vmid"><span class="nowrap">LinkDB</span></th> <td class="td21 defd"><button class="btn" onclick="location.href='https://www.genome.jp/dbget-bin/get_linkdb?compound+C00036';return false;">All DBs</button></td></tr> <tr><th class="th20 deft tal vtop"><span class="nowrap">KCF data</span></th> <td class="td20 defd"><button class="btn" id="kcfb1">Show</button><div class="kcfd" id="kcfd1"><br>ATOM 9<br> 1 O6a O 17.9200 -20.5800<br> 2 C6a C 19.1324 -21.2800<br> 3 C1b C 20.3449 -20.5800<br> 4 C5a C 21.5573 -21.2800<br> 5 C6a C 22.7697 -20.5800<br> 6 O6a O 23.9822 -21.2800<br> 7 O6a O 19.1324 -22.6798<br> 8 O5a O 21.5573 -22.6800<br> 9 O6a O 22.7697 -19.1801<br> BOND 8<br> 1 1 2 1<br> 2 2 3 1<br> 3 3 4 1<br> 4 4 5 1<br> 5 5 6 1<br> 6 2 7 2<br> 7 4 8 2<br> 8 5 9 2<br> </div></td></tr> </table></td></tr></table> <br><span style="font-size:12px"><a href="/entry/cpd_ja:C00036">» Japanese version</a></span><br><br></td></tr></table> <a href="/dbget/">DBGET</a> integrated database retrieval system</div> </body> </html>