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  <cached-name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z))</cached-name>
  <cached-description>A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other animals, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils (Wikipedia). De novo biosynthesis of triglycerides is also known as the phosphatidic acid pathway, and it is mainly associated with the liver and adipose tissue. All membrane-localized enzymes are coloured dark green in the image. First, dihydroxyacetone phosphate (or glycerone phosphate) from glycolysis is used by the cytosolic enzyme glycerol-3-phosphate dehydrogenase [NAD(+)] to synthesize sn-glycerol 3-phosphate. Second, the mitochondrial outer membrane enzyme glycerol-3-phosphate acyltransferase esterifies an acyl-group to the sn-1 position of sn-glycerol 3-phosphate to form 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid or LPA). The next three steps are localized to the endoplasmic reticulum membrane. The enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase converts LPA into phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by esterifying an acyl-group to the sn-2 position of the glycerol backbone. Next, magnesium-dependent phosphatidate phosphatase catalyzes the conversion of phosphatidic acid into diacylglycerol. Last, the enzyme diacylglycerol O-acyltransferase synthesizes triacylglycerol from diacylglycerol and a fatty acyl-CoA.</cached-description>
  <cached-subject>Metabolic</cached-subject>
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          <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z))</name>
          <description>A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other animals, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils (Wikipedia). De novo biosynthesis of triglycerides is also known as the phosphatidic acid pathway, and it is mainly associated with the liver and adipose tissue. All membrane-localized enzymes are coloured dark green in the image. First, dihydroxyacetone phosphate (or glycerone phosphate) from glycolysis is used by the cytosolic enzyme glycerol-3-phosphate dehydrogenase [NAD(+)] to synthesize sn-glycerol 3-phosphate. Second, the mitochondrial outer membrane enzyme glycerol-3-phosphate acyltransferase esterifies an acyl-group to the sn-1 position of sn-glycerol 3-phosphate to form 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid or LPA). The next three steps are localized to the endoplasmic reticulum membrane. The enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase converts LPA into phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by esterifying an acyl-group to the sn-2 position of the glycerol backbone. Next, magnesium-dependent phosphatidate phosphatase catalyzes the conversion of phosphatidic acid into diacylglycerol. Last, the enzyme diacylglycerol O-acyltransferase synthesizes triacylglycerol from diacylglycerol and a fatty acyl-CoA.</description>
          <subject>Metabolic</subject>
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              <altext>Glycolysis</altext>
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              <pubmed-id>8944226</pubmed-id>
              <text>Lehner R, Kuksis A: Biosynthesis of triacylglycerols. Prog Lipid Res. 1996;35(2):169-201.</text>
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            <name>Platelet </name>
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          <compound>
            <id type="integer">1144</id>
            <name>NADH</name>
            <hmdb-id>HMDB0001487</hmdb-id>
            <description>NADH 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).</description>
            <cas>58-68-4</cas>
            <kegg-id>C00004</kegg-id>
            <pubchem-cid>439153</pubchem-cid>
            <chebi-id>16908</chebi-id>
            <biocyc-id>NADH</biocyc-id>
            <chemspider-id>388299</chemspider-id>
            <drugbank-id>DB00157</drugbank-id>
            <moldb-smiles>NC(=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]1O</moldb-smiles>
            <moldb-formula>C21H29N7O14P2</moldb-formula>
            <moldb-inchi>InChI=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/s1</moldb-inchi>
            <moldb-inchikey>BOPGDPNILDQYTO-NNYOXOHSSA-N</moldb-inchikey>
            <moldb-iupac>[({[(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 acid</moldb-iupac>
            <moldb-average-mass>665.441</moldb-average-mass>
            <moldb-mono-mass>665.124771695</moldb-mono-mass>
            <moldb-alogps-logs>-2.35</moldb-alogps-logs>
            <moldb-donor-count>8</moldb-donor-count>
            <moldb-traditional-iupac>NADH</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">0</moldb-formal-charge>
            <moldb-physiological-charge type="integer">-2</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id>FDB022649</foodb-id>
            <synonyms>1,4-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 dinucleotide</synonyms>
            <pwc-id>PW_C001144</pwc-id>
            <short-name>NADH</short-name>
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            <id type="integer">1134</id>
            <name>Dihydroxyacetone phosphate</name>
            <hmdb-id>HMDB0001473</hmdb-id>
            <description>Dihydroxyacetone 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.</description>
            <cas>57-04-5</cas>
            <kegg-id>C00111</kegg-id>
            <pubchem-cid>668</pubchem-cid>
            <chebi-id>16108</chebi-id>
            <biocyc-id>DIHYDROXY-ACETONE-PHOSPHATE</biocyc-id>
            <chemspider-id>648</chemspider-id>
            <drugbank-id>DB04326</drugbank-id>
            <moldb-smiles>OCC(=O)COP(O)(O)=O</moldb-smiles>
            <moldb-formula>C3H7O6P</moldb-formula>
            <moldb-inchi>InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)</moldb-inchi>
            <moldb-inchikey>GNGACRATGGDKBX-UHFFFAOYSA-N</moldb-inchikey>
            <moldb-iupac>(3-hydroxy-2-oxopropoxy)phosphonic acid</moldb-iupac>
            <moldb-average-mass>170.0578</moldb-average-mass>
            <moldb-mono-mass>169.998024468</moldb-mono-mass>
            <moldb-alogps-logs>-0.89</moldb-alogps-logs>
            <moldb-donor-count>3</moldb-donor-count>
            <moldb-traditional-iupac>dihydroxyacetone-phosphate</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">0</moldb-formal-charge>
            <moldb-physiological-charge type="integer">-2</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id>FDB001618</foodb-id>
            <synonyms>1,3-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 acid</synonyms>
            <pwc-id>PW_C001134</pwc-id>
            <short-name>Dhapp</short-name>
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                <biological-state-id type="integer">502</biological-state-id>
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            <id type="integer">721</id>
            <name>NAD</name>
            <hmdb-id>HMDB0000902</hmdb-id>
            <description>NAD (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).</description>
            <cas>53-84-9</cas>
            <kegg-id>C00003</kegg-id>
            <pubchem-cid>5893</pubchem-cid>
            <chebi-id>15846</chebi-id>
            <biocyc-id>NAD</biocyc-id>
            <chemspider-id>5682</chemspider-id>
            <drugbank-id nil="true"/>
            <moldb-smiles>NC(=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]1O</moldb-smiles>
            <moldb-formula>C21H28N7O14P2</moldb-formula>
            <moldb-inchi>InChI=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/s1</moldb-inchi>
            <moldb-inchikey>BAWFJGJZGIEFAR-NNYOXOHSSA-O</moldb-inchikey>
            <moldb-iupac>1-[(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-ylium</moldb-iupac>
            <moldb-average-mass>664.433</moldb-average-mass>
            <moldb-mono-mass>664.116946663</moldb-mono-mass>
            <moldb-alogps-logs>-2.59</moldb-alogps-logs>
            <moldb-donor-count>8</moldb-donor-count>
            <moldb-traditional-iupac>1-[(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-ylium</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">1</moldb-formal-charge>
            <moldb-physiological-charge type="integer">-1</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id>FDB022309</foodb-id>
            <synonyms>3-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-nad</synonyms>
            <pwc-id>PW_C000721</pwc-id>
            <short-name>NAD</short-name>
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                <id type="integer">150</id>
                <biological-state-id type="integer">3</biological-state-id>
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                <id type="integer">353</id>
                <biological-state-id type="integer">8</biological-state-id>
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                <id type="integer">651</id>
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                <biological-state-id type="integer">2</biological-state-id>
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            <name>Glycerol 3-phosphate</name>
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            <description>Glycerol 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).</description>
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            <kegg-id>C00093</kegg-id>
            <pubchem-cid>439162</pubchem-cid>
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            <moldb-smiles>OC[C@@H](O)COP(O)(O)=O</moldb-smiles>
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            <synonyms>1-(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 acid</synonyms>
            <pwc-id>PW_C000081</pwc-id>
            <short-name>Glyc1P</short-name>
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            <name>Eicosapentaenoyl-CoA</name>
            <hmdb-id>HMDB0060311</hmdb-id>
            <description>Eicosapentaenoyl-CoA, also known as 20:5(n-3), belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Thus, eicosapentaenoyl-CoA is considered to be a fatty ester lipid molecule. Eicosapentaenoyl-CoA is considered to be a practically insoluble (in water) and relatively neutral molecule. Eicosapentaenoyl-CoA has been primarily detected in urine. Within the cell, eicosapentaenoyl-CoA is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, eicosapentaenoyl-CoA is involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/18:2(9Z,12Z)) pathway, de novo triacylglycerol biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway, de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway, and de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway. A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of eicosapentaenoic acid.</description>
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            <kegg-id>C16165</kegg-id>
            <pubchem-cid>56927904</pubchem-cid>
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            <moldb-formula>C41H64N7O17P3S</moldb-formula>
            <moldb-inchi>InChI=1S/C41H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h5-6,8-9,11-12,14-15,17-18,28-30,34-36,40,51-52H,4,7,10,13,16,19-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/b6-5-,9-8-,12-11-,15-14-,18-17-/t30-,34-,35-,36+,40-/m1/s1</moldb-inchi>
            <moldb-inchikey>JWZLRYCDDXHXDL-LCMHIRPZSA-N</moldb-inchikey>
            <moldb-iupac>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</moldb-iupac>
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            <moldb-alogps-logs>-3.39</moldb-alogps-logs>
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            <moldb-traditional-iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy((3R)-3-hydroxy-3-{[2-({2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid</moldb-traditional-iupac>
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            <synonyms>(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA;(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-coenzyme A;all-cis-5,8,11,14,17-eicosapentaenoyl-CoA;eicosapentaenoyl-coenzyme A;icosapentaenoyl-CoA;icosapentaenoyl-coenzyme A;(5Z,8Z,11Z,14Z,17Z)-icosapentaenoyl-CoA;(5Z,8Z,11Z,14Z,17Z)-icosapentaenoyl-coenzyme A;all-cis-5,8,11,14,17-icosapentaenoyl-CoA;(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl-CoA;(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl-coenzyme A;CoA(20:5(5Z,8Z,11Z,14Z,17Z))</synonyms>
            <pwc-id>PW_C062919</pwc-id>
            <short-name>IC</short-name>
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            <name>Coenzyme A</name>
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            <description>Coenzyme 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).</description>
            <cas>85-61-0</cas>
            <kegg-id>C00010</kegg-id>
            <pubchem-cid>6816</pubchem-cid>
            <chebi-id>1146900</chebi-id>
            <biocyc-id>CO-A</biocyc-id>
            <chemspider-id>6557</chemspider-id>
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            <moldb-formula>C21H36N7O16P3S</moldb-formula>
            <moldb-inchi>InChI=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/s1</moldb-inchi>
            <moldb-inchikey>RGJOEKWQDUBAIZ-IBOSZNHHSA-N</moldb-inchikey>
            <moldb-iupac>{[(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 acid</moldb-iupac>
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            <moldb-alogps-logs>-2.22</moldb-alogps-logs>
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            <moldb-traditional-iupac>coenzyme A</moldb-traditional-iupac>
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            <foodb-id>FDB022614</foodb-id>
            <synonyms>Acetoacetyl 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 diphosphate</synonyms>
            <pwc-id>PW_C001099</pwc-id>
            <short-name>CoA</short-name>
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              <element-state>
                <id type="integer">110555</id>
                <biological-state-id type="integer">389</biological-state-id>
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              <element-state>
                <id type="integer">110561</id>
                <biological-state-id type="integer">390</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115842</id>
                <biological-state-id type="integer">399</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115847</id>
                <biological-state-id type="integer">398</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">119951</id>
                <biological-state-id type="integer">406</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120147</id>
                <biological-state-id type="integer">405</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120231</id>
                <biological-state-id type="integer">384</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120305</id>
                <biological-state-id type="integer">122</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120634</id>
                <biological-state-id type="integer">407</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120762</id>
                <biological-state-id type="integer">117</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">121406</id>
                <biological-state-id type="integer">123</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">121421</id>
                <biological-state-id type="integer">433</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">121521</id>
                <biological-state-id type="integer">125</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">121666</id>
                <biological-state-id type="integer">429</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">121682</id>
                <biological-state-id type="integer">408</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">121714</id>
                <biological-state-id type="integer">414</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122404</id>
                <biological-state-id type="integer">422</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122741</id>
                <biological-state-id type="integer">120</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122904</id>
                <biological-state-id type="integer">121</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122960</id>
                <biological-state-id type="integer">135</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">123965</id>
                <biological-state-id type="integer">447</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">123979</id>
                <biological-state-id type="integer">468</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">124079</id>
                <biological-state-id type="integer">136</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">124220</id>
                <biological-state-id type="integer">464</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">124265</id>
                <biological-state-id type="integer">450</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">124974</id>
                <biological-state-id type="integer">375</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125341</id>
                <biological-state-id type="integer">479</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125509</id>
                <biological-state-id type="integer">478</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125579</id>
                <biological-state-id type="integer">480</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125592</id>
                <biological-state-id type="integer">484</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125634</id>
                <biological-state-id type="integer">297</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126084</id>
                <biological-state-id type="integer">481</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126549</id>
                <biological-state-id type="integer">491</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126560</id>
                <biological-state-id type="integer">482</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126746</id>
                <biological-state-id type="integer">300</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126884</id>
                <biological-state-id type="integer">501</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">127046</id>
                <biological-state-id type="integer">209</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">127109</id>
                <biological-state-id type="integer">391</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">127301</id>
                <biological-state-id type="integer">205</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">127540</id>
                <biological-state-id type="integer">206</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">127667</id>
                <biological-state-id type="integer">388</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">128121</id>
                <biological-state-id type="integer">508</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">128133</id>
                <biological-state-id type="integer">502</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">128340</id>
                <biological-state-id type="integer">395</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">62937</id>
            <name>LPA(20:5(5Z,8Z,11Z,14Z,17Z)/0:0)</name>
            <hmdb-id>HMDB0114748</hmdb-id>
            <description>LPA(20:5(5Z,8Z,11Z,14Z,17Z)/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common. LPA(20:5(5Z,8Z,11Z,14Z,17Z)/0:0), in particular, consists of one chain of eicosapentaenoic acid at the C-1 position. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes.</description>
            <cas nil="true"/>
            <kegg-id>C00681</kegg-id>
            <pubchem-cid nil="true"/>
            <chebi-id>16975</chebi-id>
            <biocyc-id>ACYL-SN-GLYCEROL-3P</biocyc-id>
            <chemspider-id nil="true"/>
            <drugbank-id nil="true"/>
            <moldb-smiles>CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCC(O)COP(O)(O)=O</moldb-smiles>
            <moldb-formula>C23H37O7P</moldb-formula>
            <moldb-inchi>InChI=1S/C23H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)29-20-22(24)21-30-31(26,27)28/h3-4,6-7,9-10,12-13,15-16,22,24H,2,5,8,11,14,17-21H2,1H3,(H2,26,27,28)/b4-3-,7-6-,10-9-,13-12-,16-15-</moldb-inchi>
            <moldb-inchikey>DKFJPTBTSHHMCQ-JLNKQSITSA-N</moldb-inchikey>
            <moldb-iupac>{2-hydroxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxy}phosphonic acid</moldb-iupac>
            <moldb-average-mass>456.516</moldb-average-mass>
            <moldb-mono-mass>456.227690529</moldb-mono-mass>
            <moldb-alogps-logs>-4.91</moldb-alogps-logs>
            <moldb-donor-count>3</moldb-donor-count>
            <moldb-traditional-iupac>2-hydroxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxyphosphonic acid</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">0</moldb-formal-charge>
            <moldb-physiological-charge type="integer">-2</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id nil="true"/>
            <synonyms>1-eicosapentaenoyl-glycero-3-phosphate ;1-eicosapentaenoyl-lysophosphatidic acid  ;LPA(20:5) ;LPA(20:5(5Z,8Z,11Z,14Z,17Z)) ;LPA(20:5n3/0:0) ;LPA(20:5w3/0:0) ;LPA(20:5n3) ;LPA(20:5w3) ;Lysophosphatidic acid(20:5(5Z,8Z,11Z,14Z,17Z)/0:0) ;Lysophosphatidic acid(20:5) ;Lysophosphatidic acid(20:5(5Z,8Z,11Z,14Z,17Z)) ;Lysophosphatidic acid(20:5n3/0:0) ;Lysophosphatidic acid(20:5w3/0:0) ;Lysophosphatidic acid(20:5n3) ;Lysophosphatidic acid(20:5w3)</synonyms>
            <pwc-id>PW_C062937</pwc-id>
            <short-name>LPA(20:</short-name>
            <element-states>
              <element-state>
                <id type="integer">25858</id>
                <biological-state-id type="integer">22</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">25859</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">87089</id>
                <biological-state-id type="integer">329</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">87090</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">100852</id>
                <biological-state-id type="integer">382</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">100853</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115509</id>
                <biological-state-id type="integer">389</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115510</id>
                <biological-state-id type="integer">390</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">62926</id>
            <name>Erucoyl-CoA</name>
            <hmdb-id>HMDB0062217</hmdb-id>
            <description>Erucoyl-CoA, also known as C22:1(N-9) -CoA or ercoyl-coenzyme A, belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more. Thus, erucoyl-CoA is considered to be a fatty ester lipid molecule. Erucoyl-CoA is considered to be a practically insoluble (in water) and relatively neutral molecule. Erucoyl-CoA has been primarily detected in urine. Within the cell, erucoyl-CoA is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, erucoyl-CoA is involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway, de novo triacylglycerol biosynthesis TG(18:0/22:2(13Z,16Z)/22:1(13Z)) pathway, de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:1(13Z)) pathway. A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of erucic acid.</description>
            <cas nil="true"/>
            <kegg-id>C16531</kegg-id>
            <pubchem-cid>71448925</pubchem-cid>
            <chebi-id>74106</chebi-id>
            <biocyc-id nil="true"/>
            <chemspider-id nil="true"/>
            <drugbank-id nil="true"/>
            <moldb-smiles>CCCCCCCC\C=C/CCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</moldb-smiles>
            <moldb-formula>C43H76N7O17P3S</moldb-formula>
            <moldb-inchi>InChI=1S/C43H76N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h11-12,30-32,36-38,42,53-54H,4-10,13-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/b12-11-/t32-,36-,37-,38+,42-/m1/s1</moldb-inchi>
            <moldb-inchikey>OWGHRDKRIGXBJM-SPZFTOIUSA-N</moldb-inchikey>
            <moldb-iupac>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(13Z)-docos-13-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</moldb-iupac>
            <moldb-average-mass>1088.09</moldb-average-mass>
            <moldb-mono-mass>1087.423126183</moldb-mono-mass>
            <moldb-alogps-logs>-3.69</moldb-alogps-logs>
            <moldb-donor-count>9</moldb-donor-count>
            <moldb-traditional-iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-{[2-({2-[(13Z)-docos-13-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">0</moldb-formal-charge>
            <moldb-physiological-charge type="integer">-4</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id nil="true"/>
            <synonyms>13Z-docosenoyl-CoA;13Z-docosenoyl-coenzyme A;erucoyl-coenzyme A;CoA(22:1(13Z))</synonyms>
            <pwc-id>PW_C062926</pwc-id>
            <short-name>EC</short-name>
            <element-states>
              <element-state>
                <id type="integer">25766</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">33479</id>
                <biological-state-id type="integer">22</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">81882</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">87232</id>
                <biological-state-id type="integer">329</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">95742</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">100995</id>
                <biological-state-id type="integer">382</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">109088</id>
                <biological-state-id type="integer">288</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">128883</id>
                <biological-state-id type="integer">398</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">62637</id>
            <name>PA(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
            <hmdb-id>HMDB0115216</hmdb-id>
            <description>PA(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)), in particular, consists of one chain of eicosapentaenoic acid at the C-1 position and one chain of erucic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.</description>
            <cas nil="true"/>
            <kegg-id>C00416</kegg-id>
            <pubchem-cid nil="true"/>
            <chebi-id>16337</chebi-id>
            <biocyc-id>L-PHOSPHATIDATE</biocyc-id>
            <chemspider-id nil="true"/>
            <drugbank-id nil="true"/>
            <moldb-smiles>[H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC</moldb-smiles>
            <moldb-formula>C45H77O8P</moldb-formula>
            <moldb-inchi>InChI=1S/C45H77O8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-45(47)53-43(42-52-54(48,49)50)41-51-44(46)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,17-20,25,27,31,33,43H,3-5,7,9-11,13,15-16,21-24,26,28-30,32,34-42H2,1-2H3,(H2,48,49,50)/b8-6-,14-12-,19-17-,20-18-,27-25-,33-31-/t43-/m1/s1</moldb-inchi>
            <moldb-inchikey>DTTVUTICRKIUMH-NPUXTLKISA-N</moldb-inchikey>
            <moldb-iupac>[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxy]phosphonic acid</moldb-iupac>
            <moldb-average-mass>777.077</moldb-average-mass>
            <moldb-mono-mass>776.535606437</moldb-mono-mass>
            <moldb-alogps-logs>-7.11</moldb-alogps-logs>
            <moldb-donor-count>2</moldb-donor-count>
            <moldb-traditional-iupac>(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxyphosphonic acid</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">0</moldb-formal-charge>
            <moldb-physiological-charge type="integer">-2</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id nil="true"/>
            <synonyms>1-eicosapentaenoyl-2-erucoyl-sn-glycero-3-phosphate ;1-eicosapentaenoyl-2-erucoyl-sn-phosphatidic acid ;PA(20:5/22:1) ;PA(20:5n3/22:1n9) ;PA(20:5w3/22:1w9) ;PA(42:6) ;Phosphatidic acid(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)) ;Phosphatidic acid(20:5/22:1) ;Phosphatidic acid(20:5n3/22:1n9) ;Phosphatidic acid(20:5w3/22:1w9) ;Phosphatidic acid(42:6) ;Phosphatidate(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)) ;Phosphatidate(20:5/22:1) ;Phosphatidate(20:5n3/22:1n9) ;Phosphatidate(20:5w3/22:1w9) ;Phosphatidate(42:6)</synonyms>
            <pwc-id>PW_C062637</pwc-id>
            <short-name>PA42:6 </short-name>
            <element-states>
              <element-state>
                <id type="integer">36453</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">87114</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">100877</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">1420</id>
            <name>Water</name>
            <hmdb-id>HMDB0002111</hmdb-id>
            <description>Water 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).</description>
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            <name>DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0)</name>
            <hmdb-id>HMDB0007580</hmdb-id>
            <description>DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0), in particular, consists of one chain of eicosapentaenoic acid at the C-1 position and one chain of erucic acid at the C-2 position. The eicosapentaenoic acid moiety is derived from fish oils, liver and kidney, while the erucic acid moiety is derived from seed oils and avocados. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.</description>
            <cas nil="true"/>
            <kegg-id>C00165</kegg-id>
            <pubchem-cid>9543917</pubchem-cid>
            <chebi-id nil="true"/>
            <biocyc-id>DIACYLGLYCEROL</biocyc-id>
            <chemspider-id>7822867</chemspider-id>
            <drugbank-id nil="true"/>
            <moldb-smiles>[H][C@](CO)(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC</moldb-smiles>
            <moldb-formula>C45H76O5</moldb-formula>
            <moldb-inchi>InChI=1S/C45H76O5/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-45(48)50-43(41-46)42-49-44(47)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,17-20,25,27,31,33,43,46H,3-5,7,9-11,13,15-16,21-24,26,28-30,32,34-42H2,1-2H3/b8-6-,14-12-,19-17-,20-18-,27-25-,33-31-/t43-/m0/s1</moldb-inchi>
            <moldb-inchikey>RBNQMECWIQORFH-ONNHQCRXSA-N</moldb-inchikey>
            <moldb-iupac>(2S)-1-hydroxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propan-2-yl (13Z)-docos-13-enoate</moldb-iupac>
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            <moldb-alogps-logs>-7.87</moldb-alogps-logs>
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            <moldb-traditional-iupac>diacylglycerol</moldb-traditional-iupac>
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            <moldb-physiological-charge type="integer">0</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id>FDB024773</foodb-id>
            <synonyms>1-eicosapentaenoyl-2-erucoyl-sn-glycerol;Dag(20:5/22:1);Dag(20:5n3/22:1n9);Dag(20:5w3/22:1w9);Dag(42:6);Dg(20:5/22:1);Dg(20:5n3/22:1n9);Dg(20:5w3/22:1w9);Dg(42:6);Diacylglycerol;Diacylglycerol(20:5/22:1);Diacylglycerol(20:5n3/22:1n9);Diacylglycerol(20:5w3/22:1w9);Diacylglycerol(42:6);Diglyceride</synonyms>
            <pwc-id>PW_C003631</pwc-id>
            <short-name>DG42:6</short-name>
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            <name>Phosphate</name>
            <hmdb-id>HMDB0001429</hmdb-id>
            <description>Phosphate 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&lt;sup&gt;2-&lt;/sup&gt;&lt;sub&gt;4&lt;/sub&gt; and H&lt;sub&gt;2&lt;/sub&gt;PO&lt;sup&gt;-&lt;/sup&gt;&lt;sub&gt;4&lt;/sub&gt; 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.</description>
            <cas>14265-44-2</cas>
            <kegg-id>C00009</kegg-id>
            <pubchem-cid>1061</pubchem-cid>
            <chebi-id>18367</chebi-id>
            <biocyc-id>CPD-8587</biocyc-id>
            <chemspider-id>1032</chemspider-id>
            <drugbank-id></drugbank-id>
            <moldb-smiles>[O-]P([O-])([O-])=O</moldb-smiles>
            <moldb-formula>O4P</moldb-formula>
            <moldb-inchi>InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3</moldb-inchi>
            <moldb-inchikey>NBIIXXVUZAFLBC-UHFFFAOYSA-K</moldb-inchikey>
            <moldb-iupac>phosphoric acid</moldb-iupac>
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            <moldb-mono-mass>94.95342</moldb-mono-mass>
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            <moldb-traditional-iupac>phosphoric acid</moldb-traditional-iupac>
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            <moldb-physiological-charge type="integer">-2</moldb-physiological-charge>
            <drugbank-metabolite-id>DBMET00532</drugbank-metabolite-id>
            <foodb-id>FDB022617</foodb-id>
            <synonyms>Nfb 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 ion</synonyms>
            <pwc-id>PW_C001104</pwc-id>
            <short-name>Pi</short-name>
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            <description>Docosadienoyl-CoA, also known as CoA(22:2(13Z,16Z)), belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more. Docosadienoyl-CoA is considered to be a practically insoluble (in water) and relatively neutral molecule. Docosadienoyl-CoA has been primarily detected in urine. Within the cell, docosadienoyl-CoA is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, docosadienoyl-CoA is involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(18:1(9Z)/16:0/22:2(13Z,16Z)) pathway, de novo triacylglycerol biosynthesis TG(20:3(8Z,11Z,14Z)/18:1(11Z)/22:2(13Z,16Z)) pathway, de novo triacylglycerol biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z)) pathway, and de novo triacylglycerol biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway. A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of docosadienoic acid.</description>
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            <moldb-iupac>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(13Z,16Z)-docosa-13,16-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</moldb-iupac>
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            <moldb-traditional-iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-{[2-({2-[(13Z,16Z)-docosa-13,16-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid</moldb-traditional-iupac>
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            <synonyms>(13Z,16Z)-docosadienoyl-CoA;(13Z,16Z)-docosadienoyl-coenzyme A;docosadienoyl-coenzyme A;CoA(22:2(13Z,16Z))</synonyms>
            <pwc-id>PW_C062947</pwc-id>
            <short-name>DC</short-name>
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            <description>Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z)), in particular, consists of one chain of eicosapentaenoic acid at the C-1 position, one chain of erucic acid at the C-2 position, and one chain of docosadienoic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, and play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins.</description>
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            <moldb-traditional-iupac>(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl (13Z,16Z)-docosa-13,16-dienoate</moldb-traditional-iupac>
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            <synonyms>1-eicosapentaenoyl-2-erucoyl-3-docosadienoyl-glycerol;TG(20:5/22:1/22:2);TG(20:5n3/22:1n9/22:2n6);TG(20:5w3/22:1w9/22:2w6);TG(64:8);Tag(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z));Tag(20:5/22:1/22:2);Tag(20:5n3/22:1n9/22:2n6);Tag(20:5w3/22:1w9/22:2w6);Tag(64:8);Triacylglycerol(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z));Triacylglycerol(20:5/22:1/22:2);Triacylglycerol(20:5n3/22:1n9/22:2n6);Triacylglycerol(20:5w3/22:1w9/22:2w6);Triacylglycerol(64:8);Triacylglycerol;Triglyceride</synonyms>
            <pwc-id>PW_C097831</pwc-id>
            <short-name>TG64:8</short-name>
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            <description>Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.</description>
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            <synonyms>Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+</synonyms>
            <pwc-id>PW_C000423</pwc-id>
            <short-name>Mg2+</short-name>
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            <id type="integer">7736</id>
            <name>Unknown</name>
            <uniprot-id>Unknown</uniprot-id>
            <description nil="true"/>
            <hmdbp-id nil="true"/>
            <gene-name nil="true"/>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">12</species-id>
            <ec-numbers>3.1.1.1, 3.1.1.56</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">5529</id>
                <biological-state-id type="integer">130</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79334</id>
                <biological-state-id type="integer">111</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79335</id>
                <biological-state-id type="integer">133</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79336</id>
                <biological-state-id type="integer">112</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79532</id>
                <biological-state-id type="integer">113</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79948</id>
                <biological-state-id type="integer">329</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79951</id>
                <biological-state-id type="integer">134</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79967</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">81809</id>
                <biological-state-id type="integer">132</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">131707</id>
                <biological-state-id type="integer">115</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">131712</id>
                <biological-state-id type="integer">128</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132238</id>
                <biological-state-id type="integer">523</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132246</id>
                <biological-state-id type="integer">328</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132274</id>
                <biological-state-id type="integer">336</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132323</id>
                <biological-state-id type="integer">114</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132364</id>
                <biological-state-id type="integer">332</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132366</id>
                <biological-state-id type="integer">116</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132572</id>
                <biological-state-id type="integer">326</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132577</id>
                <biological-state-id type="integer">535</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132581</id>
                <biological-state-id type="integer">538</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132582</id>
                <biological-state-id type="integer">348</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132583</id>
                <biological-state-id type="integer">539</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132584</id>
                <biological-state-id type="integer">541</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">132863</id>
                <biological-state-id type="integer">362</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">133487</id>
                <biological-state-id type="integer">354</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">134882</id>
                <biological-state-id type="integer">404</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">14689</id>
            <name>Phosphatidate phosphatase LPIN1</name>
            <uniprot-id>Q91ZP3</uniprot-id>
            <description>
Plays important roles in controlling the metabolism of fatty acids at different levels. Acts as a magnesium-dependent phosphatidate phosphatase enzyme which catalyzes the conversion of phosphatidic acid to diacylglycerol during triglyceride, phosphatidylcholine and phosphatidylethanolamine biosynthesis. Acts also as nuclear transcriptional coactivator for PPARGC1A/PPARA regulatory pathway to modulate lipid metabolism gene expression. Is involved in adipocyte differentiation. Isoform 1 is recruited at the mitochondrion outer membrane and is involved in mitochondrial fission by converting phosphatidic acid to diacylglycerol.
</description>
            <hmdbp-id nil="true"/>
            <gene-name>Lpin1</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">12</species-id>
            <ec-numbers>3.1.3.4</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">81832</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">14270</id>
            <name>Glycerol-3-phosphate acyltransferase 1, mitochondrial</name>
            <uniprot-id>Q61586</uniprot-id>
            <description>
Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis.
</description>
            <hmdbp-id nil="true"/>
            <gene-name>Gpam</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">12</species-id>
            <ec-numbers>2.3.1.15</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">79566</id>
                <biological-state-id type="integer">332</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79571</id>
                <biological-state-id type="integer">329</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79714</id>
                <biological-state-id type="integer">112</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">13805</id>
            <name>1-Acyl-sn-glycerol-3-phosphate acyltransferase beta</name>
            <uniprot-id>Q8K3K7</uniprot-id>
            <description>
Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
</description>
            <hmdbp-id nil="true"/>
            <gene-name>Agpat2</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">12</species-id>
            <ec-numbers>2.3.1.51</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">78568</id>
                <biological-state-id type="integer">130</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79567</id>
                <biological-state-id type="integer">332</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79569</id>
                <biological-state-id type="integer">132</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79572</id>
                <biological-state-id type="integer">350</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79689</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79692</id>
                <biological-state-id type="integer">345</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">13971</id>
            <name>Diacylglycerol O-acyltransferase 1</name>
            <uniprot-id>Q9Z2A7</uniprot-id>
            <description>
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. In liver, plays a role in esterifying exogenous fatty acids to glycerol. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders.
</description>
            <hmdbp-id nil="true"/>
            <gene-name>Dgat1</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">12</species-id>
            <ec-numbers>2.3.1.20; 2.3.1.76</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">79799</id>
                <biological-state-id type="integer">132</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79975</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
            </element-states>
          </protein>
        </proteins>
        <protein-complexes>
          <protein-complex>
            <id type="integer">6963</id>
            <name>Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic</name>
            <species-id type="integer">12</species-id>
            <pwp-id>PW_P006963</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">14777</id>
                <protein-id type="integer">14072</protein-id>
                <stoichiometry type="integer">2</stoichiometry>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
          <protein-complex>
            <id type="integer">7497</id>
            <name>Glycerol-3-phosphate acyltransferase</name>
            <species-id type="integer">12</species-id>
            <pwp-id>PW_P007497</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">15362</id>
                <protein-id type="integer">14270</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
          <protein-complex>
            <id type="integer">7507</id>
            <name>1-Acyl-sn-glycerol-3-phosphate acyltransferase</name>
            <species-id type="integer">12</species-id>
            <pwp-id>PW_P007507</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">15372</id>
                <protein-id type="integer">13805</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
          <protein-complex>
            <id type="integer">7505</id>
            <name>Phosphatidate phosphatase</name>
            <species-id type="integer">12</species-id>
            <pwp-id>PW_P007505</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">15370</id>
                <protein-id type="integer">14689</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
            <protein_complex-cofactors>
              <protein-complex-cofactor>
                <id type="integer">809</id>
                <compound-id type="integer">423</compound-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-cofactor>
            </protein_complex-cofactors>
          </protein-complex>
          <protein-complex>
            <id type="integer">7506</id>
            <name>Diacylglycerol O-acyltransferase</name>
            <species-id type="integer">12</species-id>
            <pwp-id>PW_P007506</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">15371</id>
                <protein-id type="integer">13971</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
        </protein-complexes>
        <reactions>
          <reaction>
            <id type="integer">110716</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R110716</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">402779</id>
                <element-id type="integer">1144</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">true</currency>
              </reaction-left-element>
              <reaction-left-element>
                <id type="integer">402780</id>
                <element-id type="integer">40034</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">true</currency>
              </reaction-left-element>
              <reaction-left-element>
                <id type="integer">402781</id>
                <element-id type="integer">1134</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-left-element>
            </reaction-left-elements>
            <reaction-right-elements>
              <reaction-right-element>
                <id type="integer">402782</id>
                <element-id type="integer">721</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">true</currency>
              </reaction-right-element>
              <reaction-right-element>
                <id type="integer">402783</id>
                <element-id type="integer">81</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-right-element>
            </reaction-right-elements>
            <reaction-enzymes>
              <reaction-enzyme>
                <id type="integer">101050</id>
                <protein-complex-id type="integer">6963</protein-complex-id>
                <enzyme-class nil="true"/>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
          <reaction>
            <id type="integer">116915</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R116915</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">427680</id>
                <element-id type="integer">62919</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-left-element>
              <reaction-left-element>
                <id type="integer">427681</id>
                <element-id type="integer">81</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-left-element>
            </reaction-left-elements>
            <reaction-right-elements>
              <reaction-right-element>
                <id type="integer">427682</id>
                <element-id type="integer">1099</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-right-element>
              <reaction-right-element>
                <id type="integer">427683</id>
                <element-id type="integer">62937</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-right-element>
            </reaction-right-elements>
            <reaction-enzymes>
              <reaction-enzyme>
                <id type="integer">107091</id>
                <protein-complex-id type="integer">7497</protein-complex-id>
                <enzyme-class nil="true"/>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
          <reaction>
            <id type="integer">116939</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R116939</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">427776</id>
                <element-id type="integer">62937</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-left-element>
              <reaction-left-element>
                <id type="integer">427777</id>
                <element-id type="integer">62926</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-left-element>
            </reaction-left-elements>
            <reaction-right-elements>
              <reaction-right-element>
                <id type="integer">427778</id>
                <element-id type="integer">1099</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-right-element>
              <reaction-right-element>
                <id type="integer">427779</id>
                <element-id type="integer">62637</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-right-element>
            </reaction-right-elements>
            <reaction-enzymes>
              <reaction-enzyme>
                <id type="integer">107115</id>
                <protein-complex-id type="integer">7507</protein-complex-id>
                <enzyme-class nil="true"/>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
          <reaction>
            <id type="integer">116940</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R116940</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">427780</id>
                <element-id type="integer">62637</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-left-element>
              <reaction-left-element>
                <id type="integer">427781</id>
                <element-id type="integer">1420</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">true</currency>
              </reaction-left-element>
            </reaction-left-elements>
            <reaction-right-elements>
              <reaction-right-element>
                <id type="integer">427782</id>
                <element-id type="integer">3631</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-right-element>
              <reaction-right-element>
                <id type="integer">427783</id>
                <element-id type="integer">1104</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">true</currency>
              </reaction-right-element>
            </reaction-right-elements>
            <reaction-enzymes>
              <reaction-enzyme>
                <id type="integer">107116</id>
                <protein-complex-id type="integer">7505</protein-complex-id>
                <enzyme-class nil="true"/>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
          <reaction>
            <id type="integer">116942</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R116942</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">427788</id>
                <element-id type="integer">3631</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-left-element>
              <reaction-left-element>
                <id type="integer">427789</id>
                <element-id type="integer">62947</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-left-element>
            </reaction-left-elements>
            <reaction-right-elements>
              <reaction-right-element>
                <id type="integer">427790</id>
                <element-id type="integer">97831</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-right-element>
              <reaction-right-element>
                <id type="integer">427791</id>
                <element-id type="integer">1099</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-right-element>
            </reaction-right-elements>
            <reaction-enzymes>
              <reaction-enzyme>
                <id type="integer">107118</id>
                <protein-complex-id type="integer">7506</protein-complex-id>
                <enzyme-class nil="true"/>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
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        <reaction-coupled-transports>
        </reaction-coupled-transports>
        <transports>
          <transport>
            <id type="integer">1580</id>
            <pwt-id>PW_T001580</pwt-id>
            <transport-type nil="true"/>
            <transport-elements>
              <transport-element>
                <id type="integer">1823</id>
                <element-id type="integer">62937</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <left-biological-state-id type="integer">329</left-biological-state-id>
                <right-biological-state-id type="integer">331</right-biological-state-id>
                <direction>Right</direction>
              </transport-element>
            </transport-elements>
          </transport>
        </transports>
        <interactions>
        </interactions>
        <bound-visualizations>
        </bound-visualizations>
        <compound-locations>
          <compound-location>
            <id type="integer">1674303</id>
            <compound-id type="integer">1144</compound-id>
            <biological-state-id type="integer">132</biological-state-id>
            <visualization-template-id type="integer">60</visualization-template-id>
            <hidden type="boolean">false</hidden>
            <x type="integer">846</x>
            <y type="integer">367</y>
            <zindex type="integer">10</zindex>
            <font-size>regular</font-size>
            <width>50</width>
            <height>30</height>
          </compound-location>
          <compound-location>
            <id type="integer">1674304</id>
            <compound-id type="integer">40034</compound-id>
            <biological-state-id type="integer">132</biological-state-id>
            <visualization-template-id type="integer">55</visualization-template-id>
            <hidden type="boolean">false</hidden>
            <x type="integer">827</x>
            <y type="integer">242</y>
            <zindex type="integer">10</zindex>
            <font-size>regular</font-size>
            <width>78</width>
            <height>78</height>
          </compound-location>
          <compound-location>
            <id type="integer">1674305</id>
            <compound-id type="integer">1134</compound-id>
            <biological-state-id type="integer">132</biological-state-id>
            <visualization-template-id type="integer">3</visualization-template-id>
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