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  <cached-name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</cached-name>
  <cached-description>Cardiolipin (CL) is an important component of the inner mitochondrial membrane where it constitutes about 20% of the total lipid composition. It is essential for the optimal function of numerous enzymes that are involved in mitochondrial energy metabolism (Wikipedia). Cardiolipin biosynthesis occurs mainly in the mitochondria, but there also exists an alternative synthesis route for CDP-diacylglycerol that takes place in the endoplasmic reticulum. This second route may supplement this pathway. 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). Third, the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase converts LPA into phosphatidic acid (PA or 1,2-diacyl-sn-glycerol 3-phosphate) by esterifying an acyl-group to the sn-2 position of the glycerol backbone. PA is then transferred to the inner mitochondrial membrane to continue cardiolipin synthesis. Fourth, magnesium-dependent phosphatidate cytidylyltransferase catalyzes the conversion of PA into CDP-diacylglycerol. Fifth, CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase synthesizes phosphatidylglycerophosphate (PGP). Sixth, phosphatidylglycerophosphatase and protein-tyrosine phosphatase dephosphorylates PGP to form phosphatidylglycerol (PG). Last, cardiolipin synthase catalyzes the synthesis of cardiolipin by transferring a phosphatidyl group from a second CDP-diacylglycerol to PG. It requires a divalent metal cation cofactor.</cached-description>
  <cached-subject>Metabolic</cached-subject>
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          <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
          <description>Cardiolipin (CL) is an important component of the inner mitochondrial membrane where it constitutes about 20% of the total lipid composition. It is essential for the optimal function of numerous enzymes that are involved in mitochondrial energy metabolism (Wikipedia). Cardiolipin biosynthesis occurs mainly in the mitochondria, but there also exists an alternative synthesis route for CDP-diacylglycerol that takes place in the endoplasmic reticulum. This second route may supplement this pathway. 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). Third, the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase converts LPA into phosphatidic acid (PA or 1,2-diacyl-sn-glycerol 3-phosphate) by esterifying an acyl-group to the sn-2 position of the glycerol backbone. PA is then transferred to the inner mitochondrial membrane to continue cardiolipin synthesis. Fourth, magnesium-dependent phosphatidate cytidylyltransferase catalyzes the conversion of PA into CDP-diacylglycerol. Fifth, CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase synthesizes phosphatidylglycerophosphate (PGP). Sixth, phosphatidylglycerophosphatase and protein-tyrosine phosphatase dephosphorylates PGP to form phosphatidylglycerol (PG). Last, cardiolipin synthase catalyzes the synthesis of cardiolipin by transferring a phosphatidyl group from a second CDP-diacylglycerol to PG. It requires a divalent metal cation cofactor.</description>
          <subject>Metabolic</subject>
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              <altext>Glycolysis</altext>
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              <text>Parisi M, Li R, Oliver B: Lipid profiles of female and male Drosophila. BMC Res Notes. 2011 Jun 15;4:198. doi: 10.1186/1756-0500-4-198.</text>
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              <text>Tian HF, Feng JM, Wen JF: The evolution of cardiolipin biosynthesis and maturation pathways and its implications for the evolution of eukaryotes. BMC Evol Biol. 2012 Mar 13;12:32. doi: 10.1186/1471-2148-12-32.</text>
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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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                <biological-state-id type="integer">3</biological-state-id>
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                <id type="integer">2779</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>
            <cas>17989-41-2</cas>
            <kegg-id>C00093</kegg-id>
            <pubchem-cid>439162</pubchem-cid>
            <chebi-id>15978</chebi-id>
            <biocyc-id>GLYCEROL-3P</biocyc-id>
            <chemspider-id>388308</chemspider-id>
            <drugbank-id>DB02515</drugbank-id>
            <moldb-smiles>OC[C@@H](O)COP(O)(O)=O</moldb-smiles>
            <moldb-formula>C3H9O6P</moldb-formula>
            <moldb-inchi>InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1</moldb-inchi>
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            <moldb-iupac>[(2R)-2,3-dihydroxypropoxy]phosphonic acid</moldb-iupac>
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            <moldb-traditional-iupac>3-phosphoglycerol</moldb-traditional-iupac>
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            <foodb-id>FDB021800</foodb-id>
            <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>cis-Vaccenoyl-CoA</name>
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            <description>Vaccenoyl CoA is a coenzyme A derivative of vaccenic acid. There are both cis (or R) and trans (or S) forms of Vaccenoyl CoA. Vaccenoyl CoA derivatives were found to be active substrates in vitro in the acylation of glycerol 3-phosphate. It is involved in the biosynthesis and oxidation of fatty acids as well as in ceramide formation.</description>
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            <moldb-formula>C39H68N7O17P3S</moldb-formula>
            <moldb-inchi>InChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h9-10,26-28,32-34,38,49-50H,4-8,11-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b10-9+/t28-,32?,33+,34+,38-/m1/s1</moldb-inchi>
            <moldb-inchikey>HEJOXXLSCAQQGQ-HHFSZNSTSA-N</moldb-inchikey>
            <moldb-iupac>{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(11E)-octadec-11-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</moldb-iupac>
            <moldb-average-mass>1031.98</moldb-average-mass>
            <moldb-mono-mass>1031.360524011</moldb-mono-mass>
            <moldb-alogps-logs>-3.06</moldb-alogps-logs>
            <moldb-donor-count>9</moldb-donor-count>
            <moldb-traditional-iupac>[(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(11E)-octadec-11-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxyphosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</moldb-traditional-iupac>
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            <foodb-id>FDB023956</foodb-id>
            <synonyms>11-octadecenoyl coa;(11Z)-octadecenoyl-CoA;(11Z)-octadecenoyl-coenzyme A;11-octadecenoyl coenzyme a;R-11-octadecenoate;R-11-octadecenoate coa;R-11-octadecenoate coenzyme a;R-11-octadecenoic acid;R-11-octadecenoyl coa;R-11-octadecenoyl coenzyme a;Vaccenoyl coa;Vaccenoyl coenzyme a;Vaccenoyl-coa;Vaccenoyl-coenzyme;Vaccenoyl-coenzyme a;Vaccenyl coenzyme a;Cis-vaccenoyl coa;Cis-vaccenoyl coenzyme a;Cis-vaccenoyl-coa;Cis-vaccenoyl-coenzyme;Cis-vaccenoyl-coenzyme a;CoA(18:1(11Z))</synonyms>
            <pwc-id>PW_C002789</pwc-id>
            <short-name>VC</short-name>
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            <name>Coenzyme A</name>
            <hmdb-id>HMDB0001423</hmdb-id>
            <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>
            <drugbank-id nil="true"/>
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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>
            <moldb-average-mass>767.534</moldb-average-mass>
            <moldb-mono-mass>767.115208365</moldb-mono-mass>
            <moldb-alogps-logs>-2.22</moldb-alogps-logs>
            <moldb-donor-count>10</moldb-donor-count>
            <moldb-traditional-iupac>coenzyme A</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>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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                <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">55372</id>
            <name>LPA(18:1(11Z)/0:0)</name>
            <hmdb-id nil="true"/>
            <description>LPA(18:1(11Z)/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(18:1(11Z)/0:0), in particular, consists of one 11Z-octadecenoyl chain.  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>[H]\C(CCCCCC)=C(/[H])CCCCCCCCCC(=O)OCC(O)COP(O)(O)=O</moldb-smiles>
            <moldb-formula>C21H41O7P</moldb-formula>
            <moldb-inchi>InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h7-8,20,22H,2-6,9-19H2,1H3,(H2,24,25,26)/b8-7-</moldb-inchi>
            <moldb-inchikey>LWSYATLSXCUNTB-FPLPWBNLSA-N</moldb-inchikey>
            <moldb-iupac>{2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid</moldb-iupac>
            <moldb-average-mass>436.526</moldb-average-mass>
            <moldb-mono-mass>436.258990658</moldb-mono-mass>
            <moldb-alogps-logs>-5.41</moldb-alogps-logs>
            <moldb-donor-count>3</moldb-donor-count>
            <moldb-traditional-iupac>2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]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-cis-vaccenoyl-glycero-3-phosphate ;1-cis-vaccenoyl-lysophosphatidic acid  ;LPA(18:1) ;LPA(18:1(11Z)) ;LPA(18:1n7/0:0) ;LPA(18:1w7/0:0) ;LPA(18:1n7) ;LPA(18:1w7) ;Lysophosphatidic acid(18:1(11Z)/0:0) ;Lysophosphatidic acid(18:1) ;Lysophosphatidic acid(18:1(11Z)) ;Lysophosphatidic acid(18:1n7/0:0) ;Lysophosphatidic acid(18:1w7/0:0) ;Lysophosphatidic acid(18:1n7) ;Lysophosphatidic acid(18:1w7)</synonyms>
            <pwc-id>PW_C055372</pwc-id>
            <short-name>LPA(18:</short-name>
            <element-states>
              <element-state>
                <id type="integer">25718</id>
                <biological-state-id type="integer">22</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">25719</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">84451</id>
                <biological-state-id type="integer">329</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">84452</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94331</id>
                <biological-state-id type="integer">249</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">98255</id>
                <biological-state-id type="integer">382</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">98256</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">109686</id>
                <biological-state-id type="integer">288</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">113712</id>
                <biological-state-id type="integer">389</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115167</id>
                <biological-state-id type="integer">390</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">131266</id>
                <biological-state-id type="integer">399</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">131267</id>
                <biological-state-id type="integer">398</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">3912</id>
            <name>PA(18:1(11Z)/18:1(11Z))</name>
            <hmdb-id>HMDB0007862</hmdb-id>
            <description>PA(18:1(11Z)/18:1(11Z))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(18:1(11Z)/18:1(11Z)), in particular, consists of two 11Z-octadecenoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. 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>53478602</pubchem-cid>
            <chebi-id>16337</chebi-id>
            <biocyc-id>L-PHOSPHATIDATE</biocyc-id>
            <chemspider-id>24766516</chemspider-id>
            <drugbank-id nil="true"/>
            <moldb-smiles>[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/CCCCCC</moldb-smiles>
            <moldb-formula>C39H73O8P</moldb-formula>
            <moldb-inchi>InChI=1S/C39H73O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,37H,3-12,17-36H2,1-2H3,(H2,42,43,44)/b15-13-,16-14-/t37-/m1/s1</moldb-inchi>
            <moldb-inchikey>LMYYBYHAZAFVTR-RLSIPVDZSA-N</moldb-inchikey>
            <moldb-iupac>[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy]phosphonic acid</moldb-iupac>
            <moldb-average-mass>700.979</moldb-average-mass>
            <moldb-mono-mass>700.504306309</moldb-mono-mass>
            <moldb-alogps-logs>-7.02</moldb-alogps-logs>
            <moldb-donor-count>2</moldb-donor-count>
            <moldb-traditional-iupac>(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]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>FDB025054</foodb-id>
            <synonyms>1,2-di(11z-octadecenoyl)-rac-phosphatidic acid;1,2-divaccenoyl-rac-glycero-3-phosphate;Pa(18:1/18:1);Pa(18:1n7/18:1n7);Pa(18:1w7/18:1w7);Pa(36:2);Phosphatidic acid(18:1/18:1);Phosphatidic acid(18:1n7/18:1n7);Phosphatidic acid(18:1w7/18:1w7);Phosphatidic acid(36:2)</synonyms>
            <pwc-id>PW_C003912</pwc-id>
            <short-name>PA36:2</short-name>
            <element-states>
              <element-state>
                <id type="integer">31802</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">39337</id>
                <biological-state-id type="integer">22</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">39338</id>
                <biological-state-id type="integer">17</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">81323</id>
                <biological-state-id type="integer">151</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">84453</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">92827</id>
                <biological-state-id type="integer">329</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">92828</id>
                <biological-state-id type="integer">134</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94330</id>
                <biological-state-id type="integer">249</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">98257</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">103022</id>
                <biological-state-id type="integer">382</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">103023</id>
                <biological-state-id type="integer">384</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">109687</id>
                <biological-state-id type="integer">288</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">109688</id>
                <biological-state-id type="integer">223</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">113713</id>
                <biological-state-id type="integer">389</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">113714</id>
                <biological-state-id type="integer">391</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115168</id>
                <biological-state-id type="integer">390</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">131268</id>
                <biological-state-id type="integer">398</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">57</id>
            <name>Cytidine triphosphate</name>
            <hmdb-id>HMDB0000082</hmdb-id>
            <description>Cytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine.</description>
            <cas>65-47-4</cas>
            <kegg-id>C00063</kegg-id>
            <pubchem-cid>6176</pubchem-cid>
            <chebi-id>17677</chebi-id>
            <biocyc-id>CTP</biocyc-id>
            <chemspider-id>5941</chemspider-id>
            <drugbank-id>DB02431</drugbank-id>
            <moldb-smiles>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</moldb-smiles>
            <moldb-formula>C9H16N3O14P3</moldb-formula>
            <moldb-inchi>InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</moldb-inchi>
            <moldb-inchikey>PCDQPRRSZKQHHS-XVFCMESISA-N</moldb-inchikey>
            <moldb-iupac>({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</moldb-iupac>
            <moldb-average-mass>483.1563</moldb-average-mass>
            <moldb-mono-mass>482.984511771</moldb-mono-mass>
            <moldb-alogps-logs>-1.64</moldb-alogps-logs>
            <moldb-donor-count>7</moldb-donor-count>
            <moldb-traditional-iupac>CTP</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">0</moldb-formal-charge>
            <moldb-physiological-charge type="integer">-3</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id>FDB012833</foodb-id>
            <synonyms>5'-(tetrahydrogen triphosphate) cytidine;5'-ctp;Ctp;Cytidine 3'-triphosphate;Cytidine 5'-(tetrahydrogen triphosphate);Cytidine 5'-triphosphate;Cytidine 5'-triphosphoric acid;Cytidine 5-prime-triphosphate;Cytidine triphosphate;Cytidine mono;Cytidine mono(tetrahydrogen triphosphate) (ester);Cytidine-5'-triphosphate;Deoxycytosine triphosphate;H4ctp</synonyms>
            <pwc-id>PW_C000057</pwc-id>
            <short-name>CTP</short-name>
            <element-states>
              <element-state>
                <id type="integer">427</id>
                <biological-state-id type="integer">23</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">1150</id>
                <biological-state-id type="integer">8</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">2718</id>
                <biological-state-id type="integer">2</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">5766</id>
                <biological-state-id type="integer">101</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">5800</id>
                <biological-state-id type="integer">108</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">7077</id>
                <biological-state-id type="integer">188</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">7593</id>
                <biological-state-id type="integer">160</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">9137</id>
                <biological-state-id type="integer">195</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">9142</id>
                <biological-state-id type="integer">213</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">12194</id>
                <biological-state-id type="integer">164</biological-state-id>
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              <element-state>
                <id type="integer">12510</id>
                <biological-state-id type="integer">288</biological-state-id>
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                <id type="integer">15285</id>
                <biological-state-id type="integer">151</biological-state-id>
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                <biological-state-id type="integer">249</biological-state-id>
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                <id type="integer">15342</id>
                <biological-state-id type="integer">22</biological-state-id>
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                <id type="integer">15374</id>
                <biological-state-id type="integer">18</biological-state-id>
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                <id type="integer">34759</id>
                <biological-state-id type="integer">17</biological-state-id>
              </element-state>
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                <id type="integer">42650</id>
                <biological-state-id type="integer">315</biological-state-id>
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              <element-state>
                <id type="integer">77315</id>
                <biological-state-id type="integer">128</biological-state-id>
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              <element-state>
                <id type="integer">78448</id>
                <biological-state-id type="integer">111</biological-state-id>
              </element-state>
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                <id type="integer">78733</id>
                <biological-state-id type="integer">132</biological-state-id>
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                <id type="integer">79949</id>
                <biological-state-id type="integer">134</biological-state-id>
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                <biological-state-id type="integer">329</biological-state-id>
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                <id type="integer">80416</id>
                <biological-state-id type="integer">170</biological-state-id>
              </element-state>
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                <id type="integer">94784</id>
                <biological-state-id type="integer">384</biological-state-id>
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                <id type="integer">94812</id>
                <biological-state-id type="integer">125</biological-state-id>
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                <id type="integer">94817</id>
                <biological-state-id type="integer">382</biological-state-id>
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                <id type="integer">98677</id>
                <biological-state-id type="integer">223</biological-state-id>
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                <id type="integer">110633</id>
                <biological-state-id type="integer">391</biological-state-id>
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                <id type="integer">113268</id>
                <biological-state-id type="integer">395</biological-state-id>
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              <element-state>
                <id type="integer">113273</id>
                <biological-state-id type="integer">389</biological-state-id>
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            <id type="integer">170</id>
            <name>Pyrophosphate</name>
            <hmdb-id>HMDB0000250</hmdb-id>
            <description>The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.</description>
            <cas>14000-31-8</cas>
            <kegg-id>C00013</kegg-id>
            <pubchem-cid>644102</pubchem-cid>
            <chebi-id>18361</chebi-id>
            <biocyc-id>PPI</biocyc-id>
            <chemspider-id>559142</chemspider-id>
            <drugbank-id>DB04160</drugbank-id>
            <moldb-smiles>[O-]P([O-])(=O)OP([O-])([O-])=O</moldb-smiles>
            <moldb-formula>O7P2</moldb-formula>
            <moldb-inchi>InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4</moldb-inchi>
            <moldb-inchikey>XPPKVPWEQAFLFU-UHFFFAOYSA-J</moldb-inchikey>
            <moldb-iupac>(phosphonooxy)phosphonic acid</moldb-iupac>
            <moldb-average-mass>173.9433</moldb-average-mass>
            <moldb-mono-mass>173.911925378</moldb-mono-mass>
            <moldb-alogps-logs nil="true"/>
            <moldb-donor-count>4</moldb-donor-count>
            <moldb-traditional-iupac>pyrophosphoric acid</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">0</moldb-formal-charge>
            <moldb-physiological-charge type="integer">-3</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id>FDB021918</foodb-id>
            <synonyms>(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ion</synonyms>
            <pwc-id>PW_C000170</pwc-id>
            <short-name>Ppi</short-name>
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            <name>CDP-DG(18:1(11Z)/18:1(11Z))</name>
            <hmdb-id>HMDB0006988</hmdb-id>
            <description>CDP-DG(18:1(11Z)/18:1(11Z)) belongs to the family of CDP-diacylglycerols. It is a glycerophospholipid containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. CDP-DG(18:1(11Z)/18:1(11Z)), in particular, consists of two 11Z-octadecenoyl chain at positions C-1 and C2. In E. coli glycerophospholipid metabolism, The biosynthesis of CDP-diacylglycerol (CDP-DG) involves condensation of phosphatidic acid (PA) and cytidine triphosphate, with elimination of pyrophosphate, catalysed by the enzyme CDP-diacylglycerol synthase. The resulting CDP-diacylglycerol can be utilized immediately for the synthesis of phosphatidylglycerol (PG), and thence cardiolipin (CL), and of phosphatidylinositol (PI). CDP-DG(18:1(11Z)/18:1(11Z))  is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway.</description>
            <cas nil="true"/>
            <kegg-id>C00269</kegg-id>
            <pubchem-cid>24779568</pubchem-cid>
            <chebi-id>17962</chebi-id>
            <biocyc-id>CDPDIACYLGLYCEROL</biocyc-id>
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            <moldb-formula>C48H85N3O15P2</moldb-formula>
            <moldb-inchi>InChI=1S/C48H85N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-43(52)61-37-40(64-44(53)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)38-62-67(57,58)66-68(59,60)63-39-41-45(54)46(55)47(65-41)51-36-35-42(49)50-48(51)56/h13-16,35-36,40-41,45-47,54-55H,3-12,17-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b15-13-,16-14-/t40-,41-,45+,46?,47-/m1/s1</moldb-inchi>
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            <moldb-iupac>{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid</moldb-iupac>
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            <moldb-alogps-logs>-5.54</moldb-alogps-logs>
            <moldb-donor-count>5</moldb-donor-count>
            <moldb-traditional-iupac>[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic 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>FDB024182</foodb-id>
            <synonyms>1,2-di(11z-octadecenoyl)-rac-glycero-3-cdp;1,2-divaccenoyl-rac-glycero-3-cytidine-5'-diphosphate;Cdp-dg(18:1/18:1);Cdp-dg(18:1n7/18:1n7);Cdp-dg(18:1w7/18:1w7);Cdp-dg(36:2);Cdp-diacylglycerol(18:1/18:1);Cdp-diacylglycerol(18:1n7/18:1n7);Cdp-diacylglycerol(18:1w7/18:1w7);Cdp-diacylglycerol(36:2)</synonyms>
            <pwc-id>PW_C003039</pwc-id>
            <short-name>CDP-DG(</short-name>
            <element-states>
              <element-state>
                <id type="integer">37590</id>
                <biological-state-id type="integer">17</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">87512</id>
                <biological-state-id type="integer">134</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94332</id>
                <biological-state-id type="integer">249</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">101276</id>
                <biological-state-id type="integer">384</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">108663</id>
                <biological-state-id type="integer">223</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">110988</id>
                <biological-state-id type="integer">391</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">8436</id>
            <name>PGP(18:1(11Z)/18:1(11Z))</name>
            <hmdb-id>HMDB0013520</hmdb-id>
            <description>PGP(18:1(11Z)/18:1(11Z)) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(18:1(11Z)/18:1(11Z)), in particular, consists of two 11Z-octadecenoyl chains at positions C-1 and C-2. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.</description>
            <cas nil="true"/>
            <kegg-id>C03892</kegg-id>
            <pubchem-cid>53481838</pubchem-cid>
            <chebi-id>37393</chebi-id>
            <biocyc-id>L-1-PHOSPHATIDYL-GLYCEROL-P</biocyc-id>
            <chemspider-id nil="true"/>
            <drugbank-id nil="true"/>
            <moldb-smiles>[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC</moldb-smiles>
            <moldb-formula>C42H80O13P2</moldb-formula>
            <moldb-inchi>InChI=1S/C42H80O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,39-40,43H,3-12,17-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b15-13-,16-14-/t39-,40+/m0/s1</moldb-inchi>
            <moldb-inchikey>JUWFWNRVCXDDFB-HKFASTTNSA-N</moldb-inchikey>
            <moldb-iupac>[(2S)-3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid</moldb-iupac>
            <moldb-average-mass>855.037</moldb-average-mass>
            <moldb-mono-mass>854.507416632</moldb-mono-mass>
            <moldb-alogps-logs>-6.15</moldb-alogps-logs>
            <moldb-donor-count>4</moldb-donor-count>
            <moldb-traditional-iupac>(2S)-3-{[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">0</moldb-formal-charge>
            <moldb-physiological-charge type="integer">-3</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id nil="true"/>
            <synonyms>1,2-divaccenoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate);3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid;Pgp(18:1/18:1);Pgp(18:1n7/18:1n7);Pgp(18:1w7/18:1w7);Pgp(36:2)</synonyms>
            <pwc-id>PW_C008436</pwc-id>
            <short-name>PGP36:2</short-name>
            <element-states>
              <element-state>
                <id type="integer">39339</id>
                <biological-state-id type="integer">17</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">92829</id>
                <biological-state-id type="integer">134</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">103024</id>
                <biological-state-id type="integer">384</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">109689</id>
                <biological-state-id type="integer">223</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">113715</id>
                <biological-state-id type="integer">391</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">64</id>
            <name>Cytidine monophosphate</name>
            <hmdb-id>HMDB0000095</hmdb-id>
            <description>Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991].</description>
            <cas>63-37-6</cas>
            <kegg-id>C00055</kegg-id>
            <pubchem-cid>6131</pubchem-cid>
            <chebi-id>17361</chebi-id>
            <biocyc-id>CMP</biocyc-id>
            <chemspider-id>5901</chemspider-id>
            <drugbank-id nil="true"/>
            <moldb-smiles>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</moldb-smiles>
            <moldb-formula>C9H14N3O8P</moldb-formula>
            <moldb-inchi>InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</moldb-inchi>
            <moldb-inchikey>IERHLVCPSMICTF-XVFCMESISA-N</moldb-inchikey>
            <moldb-iupac>{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</moldb-iupac>
            <moldb-average-mass>323.1965</moldb-average-mass>
            <moldb-mono-mass>323.051850951</moldb-mono-mass>
            <moldb-alogps-logs>-1.30</moldb-alogps-logs>
            <moldb-donor-count>5</moldb-donor-count>
            <moldb-traditional-iupac>cytidine monophosphate</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>FDB011882</foodb-id>
            <synonyms>5'-cmp;5-cytidylate;5-cytidylic acid;Cmp;Cytidine 5'-monophosphate;Cytidine 5'-monophosphorate;Cytidine 5'-monophosphoric acid;Cytidine 5'-phosphate;Cytidine 5'-phosphorate;Cytidine 5'-phosphoric acid;Cytidine mono(dihydrogen phosphate);Cytidine monophosphate;Cytidylate;Cytidylic acid;Cytidine-5'-monophosphate;Pc;Cytidine-5'-monophosphoric acid</synonyms>
            <pwc-id>PW_C000064</pwc-id>
            <short-name>CMP</short-name>
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              <element-state>
                <id type="integer">1151</id>
                <biological-state-id type="integer">8</biological-state-id>
              </element-state>
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                <id type="integer">2512</id>
                <biological-state-id type="integer">14</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">2734</id>
                <biological-state-id type="integer">2</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">3386</id>
                <biological-state-id type="integer">18</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">4972</id>
                <biological-state-id type="integer">56</biological-state-id>
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              <element-state>
                <id type="integer">5768</id>
                <biological-state-id type="integer">101</biological-state-id>
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              <element-state>
                <id type="integer">5802</id>
                <biological-state-id type="integer">108</biological-state-id>
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                <id type="integer">7079</id>
                <biological-state-id type="integer">188</biological-state-id>
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                <id type="integer">7595</id>
                <biological-state-id type="integer">160</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">9147</id>
                <biological-state-id type="integer">249</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">9151</id>
                <biological-state-id type="integer">224</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">9257</id>
                <biological-state-id type="integer">195</biological-state-id>
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              <element-state>
                <id type="integer">12196</id>
                <biological-state-id type="integer">164</biological-state-id>
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              <element-state>
                <id type="integer">12210</id>
                <biological-state-id type="integer">151</biological-state-id>
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              <element-state>
                <id type="integer">15274</id>
                <biological-state-id type="integer">285</biological-state-id>
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              <element-state>
                <id type="integer">15336</id>
                <biological-state-id type="integer">308</biological-state-id>
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              <element-state>
                <id type="integer">15373</id>
                <biological-state-id type="integer">49</biological-state-id>
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                <id type="integer">34815</id>
                <biological-state-id type="integer">17</biological-state-id>
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                <id type="integer">42652</id>
                <biological-state-id type="integer">315</biological-state-id>
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                <id type="integer">78449</id>
                <biological-state-id type="integer">111</biological-state-id>
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                <biological-state-id type="integer">115</biological-state-id>
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                <biological-state-id type="integer">130</biological-state-id>
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                <id type="integer">78736</id>
                <biological-state-id type="integer">132</biological-state-id>
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                <biological-state-id type="integer">134</biological-state-id>
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                <biological-state-id type="integer">331</biological-state-id>
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                <id type="integer">80421</id>
                <biological-state-id type="integer">170</biological-state-id>
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                <biological-state-id type="integer">384</biological-state-id>
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                <biological-state-id type="integer">223</biological-state-id>
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                <biological-state-id type="integer">124</biological-state-id>
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                <biological-state-id type="integer">405</biological-state-id>
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                <biological-state-id type="integer">135</biological-state-id>
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                <biological-state-id type="integer">118</biological-state-id>
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                <biological-state-id type="integer">376</biological-state-id>
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                <biological-state-id type="integer">136</biological-state-id>
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                <biological-state-id type="integer">297</biological-state-id>
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                <biological-state-id type="integer">299</biological-state-id>
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                <id type="integer">126641</id>
                <biological-state-id type="integer">478</biological-state-id>
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                <id type="integer">126752</id>
                <biological-state-id type="integer">300</biological-state-id>
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                <id type="integer">127293</id>
                <biological-state-id type="integer">205</biological-state-id>
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                <id type="integer">127940</id>
                <biological-state-id type="integer">388</biological-state-id>
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                <biological-state-id type="integer">209</biological-state-id>
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                <id type="integer">128346</id>
                <biological-state-id type="integer">395</biological-state-id>
              </element-state>
            </element-states>
          </compound>
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            <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>
            <cas>7732-18-5</cas>
            <kegg-id>C00001</kegg-id>
            <pubchem-cid>962</pubchem-cid>
            <chebi-id>15377</chebi-id>
            <biocyc-id nil="true"/>
            <chemspider-id>937</chemspider-id>
            <drugbank-id nil="true"/>
            <moldb-smiles>O</moldb-smiles>
            <moldb-formula>H2O</moldb-formula>
            <moldb-inchi>InChI=1S/H2O/h1H2</moldb-inchi>
            <moldb-inchikey>XLYOFNOQVPJJNP-UHFFFAOYSA-N</moldb-inchikey>
            <moldb-iupac>water</moldb-iupac>
            <moldb-average-mass>18.0153</moldb-average-mass>
            <moldb-mono-mass>18.010564686</moldb-mono-mass>
            <moldb-alogps-logs nil="true"/>
            <moldb-donor-count>1</moldb-donor-count>
            <moldb-traditional-iupac>water</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">0</moldb-formal-charge>
            <moldb-physiological-charge type="integer">0</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id>FDB013390</foodb-id>
            <synonyms>Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;Wasser</synonyms>
            <pwc-id>PW_C001420</pwc-id>
            <short-name>H2O</short-name>
            <element-states>
              <element-state>
                <id type="integer">55</id>
                <biological-state-id type="integer">8</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94</id>
                <biological-state-id type="integer">9</biological-state-id>
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                <id type="integer">109</id>
                <biological-state-id type="integer">5</biological-state-id>
              </element-state>
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                <id type="integer">139</id>
                <biological-state-id type="integer">4</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">151</id>
                <biological-state-id type="integer">3</biological-state-id>
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              <element-state>
                <id type="integer">162</id>
                <biological-state-id type="integer">14</biological-state-id>
              </element-state>
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                <id type="integer">481</id>
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            <id type="integer">6626</id>
            <name>PG(18:1(11Z)/18:1(11Z))</name>
            <hmdb-id>HMDB0010618</hmdb-id>
            <description>PG(18:1(11Z)/18:1(11Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(18:1(11Z)/18:1(11Z)), in particular, consists of two 11Z-octadecenoyl chains at positions C-1 and C-2. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.</description>
            <cas nil="true"/>
            <kegg-id>C00344</kegg-id>
            <pubchem-cid>53480617</pubchem-cid>
            <chebi-id>17517</chebi-id>
            <biocyc-id>L-1-PHOSPHATIDYL-GLYCEROL</biocyc-id>
            <chemspider-id>24768117</chemspider-id>
            <drugbank-id nil="true"/>
            <moldb-smiles>[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC</moldb-smiles>
            <moldb-formula>C42H79O10P</moldb-formula>
            <moldb-inchi>InChI=1S/C42H79O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,39-40,43-44H,3-12,17-38H2,1-2H3,(H,47,48)/b15-13-,16-14-/t39-,40+/m0/s1</moldb-inchi>
            <moldb-inchikey>SOLXJHKVRWSNJX-HKFASTTNSA-N</moldb-inchikey>
            <moldb-iupac>[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid</moldb-iupac>
            <moldb-average-mass>775.058</moldb-average-mass>
            <moldb-mono-mass>774.541085742</moldb-mono-mass>
            <moldb-alogps-logs>-6.96</moldb-alogps-logs>
            <moldb-donor-count>3</moldb-donor-count>
            <moldb-traditional-iupac>(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid</moldb-traditional-iupac>
            <moldb-formal-charge type="integer">0</moldb-formal-charge>
            <moldb-physiological-charge type="integer">-1</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id nil="true"/>
            <synonyms>1,2-di(11z-octadecenoyl)-rac-glycero-3-phospho-(1'-glycerol);1,2-divaccenoyl-rac-glycero-3-phosphoglycerol;Gpg(18:1/18:1);Gpg(18:1n7/18:1n7);Gpg(18:1w7/18:1w7);Gpg(36:2);Pg(18:1/18:1);Pg(18:1n7/18:1n7);Pg(18:1w7/18:1w7);Pg(36:2);Phosphatidylglycerol(18:1/18:1);Phosphatidylglycerol(18:1n7/18:1n7);Phosphatidylglycerol(18:1w7/18:1w7);Phosphatidylglycerol(36:2)</synonyms>
            <pwc-id>PW_C006626</pwc-id>
            <short-name>PG36:2</short-name>
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                <id type="integer">39340</id>
                <biological-state-id type="integer">17</biological-state-id>
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                <id type="integer">92830</id>
                <biological-state-id type="integer">134</biological-state-id>
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                <id type="integer">103025</id>
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                <id type="integer">113716</id>
                <biological-state-id type="integer">391</biological-state-id>
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            <id type="integer">1104</id>
            <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>
            <moldb-average-mass>94.9714</moldb-average-mass>
            <moldb-mono-mass>94.95342</moldb-mono-mass>
            <moldb-alogps-logs nil="true"/>
            <moldb-donor-count>3</moldb-donor-count>
            <moldb-traditional-iupac>phosphoric 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>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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            <id type="integer">99574</id>
            <name>CDP-DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
            <hmdb-id nil="true"/>
            <description>CDP-DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol (CDP-DG). CDP-diacylglycerol is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols 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. CDP-DG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of alpha-linolenic acid at the C-1 position and one chain of eicosatetraenoic acid at the C-2 position. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts (perhaps only 0.05% or so of the total phospholipids).</description>
            <cas nil="true"/>
            <kegg-id nil="true"/>
            <pubchem-cid nil="true"/>
            <chebi-id nil="true"/>
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            <chemspider-id nil="true"/>
            <drugbank-id nil="true"/>
            <moldb-smiles>[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC</moldb-smiles>
            <moldb-formula>C50H79N3O15P2</moldb-formula>
            <moldb-inchi>InChI=1S/C50H79N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-46(55)66-42(39-63-45(54)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)40-64-69(59,60)68-70(61,62)65-41-43-47(56)48(57)49(67-43)53-38-37-44(51)52-50(53)58/h5-8,11-14,17-19,21-22,24,37-38,42-43,47-49,56-57H,3-4,9-10,15-16,20,23,25-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b7-5-,8-6-,13-11-,14-12-,19-17-,21-18-,24-22-/t42-,43-,47+,48?,49-/m1/s1</moldb-inchi>
            <moldb-inchikey>PJMQNPPNHMGHHI-YSULQAAFSA-N</moldb-inchikey>
            <moldb-iupac>{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphoryl}oxy)phosphinic acid</moldb-iupac>
            <moldb-average-mass>1024.136</moldb-average-mass>
            <moldb-mono-mass>1023.498642852</moldb-mono-mass>
            <moldb-alogps-logs>-5.68</moldb-alogps-logs>
            <moldb-donor-count>5</moldb-donor-count>
            <moldb-traditional-iupac>[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy)phosphoryl]oxy)phosphinic acid</moldb-traditional-iupac>
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            <moldb-physiological-charge type="integer">-2</moldb-physiological-charge>
            <drugbank-metabolite-id nil="true"/>
            <foodb-id nil="true"/>
            <synonyms>1-alpha-linolenoyl-2-eicosatetraenoyl-sn-glycero-3-CDP;1-alpha-linolenoyl-2-eicosatetraenoyl-sn-glycero-3-cytidine-5'-diphosphate;CDP-DG(18:3/20:4);CDP-DG(18:3n3/20:4n3);CDP-DG(18:3w3/20:4w3);CDP-DG(38:7);CDP-diacylglycerol(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z));CDP-diacylglycerol(18:3/20:4);CDP-diacylglycerol(18:3n3/20:4n3);CDP-diacylglycerol(18:3w3/20:4w3);CDP-diacylglycerol(38:7)</synonyms>
            <pwc-id>PW_C099574</pwc-id>
            <short-name>CDP-DG(</short-name>
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                <biological-state-id type="integer">391</biological-state-id>
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            <id type="integer">101498</id>
            <name>CL(18:1(11Z)/18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
            <hmdb-id nil="true"/>
            <description>CL(18:1(11Z)/18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) is a cardiolipin (CL). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20% of the total lipid. Cardiolipins are a "double" phospholipid because they have four fatty acid tails, instead of the usual two. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. CL(18:1(11Z)/18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of cis-vaccenic acid at the C-1 position, one chain of cis-vaccenic acid at the C-2 position, one chain of alpha-linolenic acid at the C-3 position, and one chain of eicosatetraenoic acid at the C-4 position. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. Newly synthesized cardiolipins undergo remodeling, a process carried out by the enzyme tafazzin. A mutated tafazzin gene disrupts this post-synthetic remodeling and causes Barth syndrome (BTHS), an X-linked human disease (PMID: 16973164).  BTHS patients seem to lack acyl specificity and consequently, many potential cardiolipin species can exist (PMID: 16226238).</description>
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            <chemspider-id nil="true"/>
            <drugbank-id nil="true"/>
            <moldb-smiles>[H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC</moldb-smiles>
            <moldb-formula>C83H144O17P2</moldb-formula>
            <moldb-inchi>InChI=1S/C83H144O17P2/c1-5-9-13-17-21-25-29-33-37-38-42-46-50-54-58-62-66-70-83(88)100-79(74-94-81(86)68-64-60-56-52-48-44-40-35-31-27-23-19-15-11-7-3)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-45-41-36-32-28-24-20-16-12-8-4)73-93-80(85)67-63-59-55-51-47-43-39-34-30-26-22-18-14-10-6-2/h9,11,13,15,21,23,25-28,30,32-33,35,37,40,42,46,77-79,84H,5-8,10,12,14,16-20,22,24,29,31,34,36,38-39,41,43-45,47-76H2,1-4H3,(H,89,90)(H,91,92)/b13-9-,15-11-,25-21-,27-23-,30-26-,32-28-,37-33-,40-35-,46-42-/t77-,78+,79+/m0/s1</moldb-inchi>
            <moldb-inchikey>ITKAKCMATAXMOI-AJFVVCSZSA-N</moldb-inchikey>
            <moldb-iupac>[3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinic acid</moldb-iupac>
            <moldb-average-mass>1475.996</moldb-average-mass>
            <moldb-mono-mass>1474.987877173</moldb-mono-mass>
            <moldb-alogps-logs>-7.28</moldb-alogps-logs>
            <moldb-donor-count>3</moldb-donor-count>
            <moldb-traditional-iupac>3-{[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy)phosphinic 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>CL(18:1/18:1/18:3/20:4);CL(18:1n7/18:1n7/18:3n3/20:4n3);CL(18:1w7/18:1w7/18:3w3/20:4w3);CL(74:9);Cardiolipin(18:1(11Z)/18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z));Cardiolipin(18:1/18:1/18:3/20:4);Cardiolipin(18:1n7/18:1n7/18:3n3/20:4n3);Cardiolipin(18:1w7/18:1w7/18:3w3/20:4w3);Cardiolipin(74:9)</synonyms>
            <pwc-id>PW_C101498</pwc-id>
            <short-name>CL74:9</short-name>
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                <id type="integer">113749</id>
                <biological-state-id type="integer">391</biological-state-id>
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            <gene-name>gpdh</gene-name>
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            <ec-numbers>1.1.1.8</ec-numbers>
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            <gene-name>Dhap-at</gene-name>
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            <name>CG4729, isoform E</name>
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            <gene-name>Dmel\CG4729</gene-name>
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            <genbank-id nil="true"/>
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            <name>Phosphatidate cytidylyltransferase</name>
            <uniprot-id>B6IDT4</uniprot-id>
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            <gene-name>CdsA-RA</gene-name>
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          </protein>
          <protein>
            <id type="integer">18727</id>
            <name>CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase</name>
            <uniprot-id>Q8SYL0</uniprot-id>
            <description>
Functions in the biosynthesis of the anionic phospholipids phosphatidylglycerol and cardiolipin.
</description>
            <hmdbp-id nil="true"/>
            <gene-name>PL D</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">10</species-id>
            <ec-numbers>2.7.8.5</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">131590</id>
                <biological-state-id type="integer">480</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">133611</id>
                <biological-state-id type="integer">479</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">18728</id>
            <name>FI07205p</name>
            <uniprot-id>B5RJ36</uniprot-id>
            <description nil="true"/>
            <hmdbp-id nil="true"/>
            <gene-name>Plip-RB</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">10</species-id>
            <ec-numbers></ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">131591</id>
                <biological-state-id type="integer">480</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">133612</id>
                <biological-state-id type="integer">481</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">18729</id>
            <name>Cardiolipin synthase, isoform D</name>
            <uniprot-id>A0A0B4KHW4</uniprot-id>
            <description nil="true"/>
            <hmdbp-id nil="true"/>
            <gene-name>CLS</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">10</species-id>
            <ec-numbers>2.7.8.-</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">131592</id>
                <biological-state-id type="integer">480</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">133613</id>
                <biological-state-id type="integer">481</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">15684</id>
            <name>Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic</name>
            <uniprot-id>Q9VML0</uniprot-id>
            <description nil="true"/>
            <hmdbp-id nil="true"/>
            <gene-name>Gpdh</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">10</species-id>
            <ec-numbers>1.1.1.8</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">125789</id>
                <biological-state-id type="integer">297</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126716</id>
                <biological-state-id type="integer">299</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">18730</id>
            <name>BcDNA.GH07066</name>
            <uniprot-id>Q9Y137</uniprot-id>
            <description nil="true"/>
            <hmdbp-id nil="true"/>
            <gene-name>mino</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">10</species-id>
            <ec-numbers>2.3.1.15</ec-numbers>
            <synonyms nil="true"/>
          </protein>
          <protein>
            <id type="integer">16209</id>
            <name>1-Acyl-sn-glycerol-3-phosphate acyltransferase</name>
            <uniprot-id>Q9VYJ4</uniprot-id>
            <description nil="true"/>
            <hmdbp-id nil="true"/>
            <gene-name>Dmel\CG3812</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">10</species-id>
            <ec-numbers>2.3.1.51</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">125971</id>
                <biological-state-id type="integer">495</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125985</id>
                <biological-state-id type="integer">489</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126747</id>
                <biological-state-id type="integer">300</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">16276</id>
            <name>CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase</name>
            <uniprot-id>Q9VE36</uniprot-id>
            <description>
Functions in the biosynthesis of the anionic phospholipids phosphatidylglycerol and cardiolipin.
</description>
            <hmdbp-id nil="true"/>
            <gene-name>PL D</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">10</species-id>
            <ec-numbers>2.7.8.5</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">126020</id>
                <biological-state-id type="integer">479</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">16279</id>
            <name>Phosphatidylglycerophosphatase and protein-tyrosine phosphatase 1</name>
            <uniprot-id>Q9VCI6</uniprot-id>
            <description>
Lipid phosphatase that may mediate dephosphorylation of mitochondrial proteins (By similarity). Protein phosphatase that may mediate dephosphorylation of mitochondrial proteins (By similarity). Does not dephosphorylate Akt.
</description>
            <hmdbp-id nil="true"/>
            <gene-name>PTPMT1</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">10</species-id>
            <ec-numbers>3.1.3.27; 3.1.3.16; 3.1.3.48</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">126022</id>
                <biological-state-id type="integer">481</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">16283</id>
            <name>Probable cardiolipin synthase (CMP-forming)</name>
            <uniprot-id>Q9VBN4</uniprot-id>
            <description>
Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) by specifically transferring a phosphatidyl group from CDP-diacylglycerol to phosphatidylglycerol (PG). CL is a key phospholipid in mitochondrial membranes and plays important roles in maintaining the functional integrity and dynamics of mitochondria under both optimal and stress conditions.
</description>
            <hmdbp-id nil="true"/>
            <gene-name>CLS</gene-name>
            <locus nil="true"/>
            <drugbank-id nil="true"/>
            <genbank-id nil="true"/>
            <species-id type="integer">10</species-id>
            <ec-numbers>2.7.8.41</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">126025</id>
                <biological-state-id type="integer">481</biological-state-id>
              </element-state>
            </element-states>
          </protein>
        </proteins>
        <protein-complexes>
          <protein-complex>
            <id type="integer">9595</id>
            <name>Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic</name>
            <species-id type="integer">10</species-id>
            <pwp-id>PW_P009595</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">17899</id>
                <protein-id type="integer">15684</protein-id>
                <stoichiometry type="integer">2</stoichiometry>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
          <protein-complex>
            <id type="integer">10387</id>
            <name>Glycerol-3-phosphate acyltransferase</name>
            <species-id type="integer">10</species-id>
            <pwp-id>PW_P010387</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">18772</id>
                <protein-id type="integer">18730</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
          <protein-complex>
            <id type="integer">10388</id>
            <name>1-Acyl-sn-glycerol-3-phosphate acyltransferase</name>
            <species-id type="integer">10</species-id>
            <pwp-id>PW_P010388</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">18773</id>
                <protein-id type="integer">16209</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
          <protein-complex>
            <id type="integer">10389</id>
            <name>Phosphatidate cytidylyltransferase</name>
            <species-id type="integer">10</species-id>
            <pwp-id>PW_P010389</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">18774</id>
                <protein-id type="integer">18726</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
          <protein-complex>
            <id type="integer">9669</id>
            <name>CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase, mitochondrial</name>
            <species-id type="integer">10</species-id>
            <pwp-id>PW_P009669</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">17974</id>
                <protein-id type="integer">16276</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
          <protein-complex>
            <id type="integer">9670</id>
            <name>Phosphatidylglycerophosphatase and protein-tyrosine phosphatase 1</name>
            <species-id type="integer">10</species-id>
            <pwp-id>PW_P009670</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">17975</id>
                <protein-id type="integer">16279</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
          <protein-complex>
            <id type="integer">9671</id>
            <name>Cardiolipin synthase</name>
            <species-id type="integer">10</species-id>
            <pwp-id>PW_P009671</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">17976</id>
                <protein-id type="integer">16283</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
        </protein-complexes>
        <reactions>
          <reaction>
            <id type="integer">159106</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R159106</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">596293</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">596294</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">596295</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">596296</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">596297</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">149476</id>
                <protein-complex-id type="integer">9595</protein-complex-id>
                <enzyme-class nil="true"/>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
          <reaction>
            <id type="integer">159668</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R159668</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">598542</id>
                <element-id type="integer">2789</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">598543</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">598544</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">598545</id>
                <element-id type="integer">55372</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">150038</id>
                <protein-complex-id type="integer">10387</protein-complex-id>
                <enzyme-class nil="true"/>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
          <reaction>
            <id type="integer">159669</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R159669</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">598546</id>
                <element-id type="integer">55372</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">598547</id>
                <element-id type="integer">2789</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">598548</id>
                <element-id type="integer">3912</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">598549</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">150039</id>
                <protein-complex-id type="integer">10388</protein-complex-id>
                <enzyme-class nil="true"/>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
          <reaction>
            <id type="integer">163462</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R163462</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">613723</id>
                <element-id type="integer">57</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">613724</id>
                <element-id type="integer">3912</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">613725</id>
                <element-id type="integer">170</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">613726</id>
                <element-id type="integer">3039</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">153832</id>
                <protein-complex-id type="integer">10389</protein-complex-id>
                <enzyme-class>2.7.7.41</enzyme-class>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
          <reaction>
            <id type="integer">163463</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R163463</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">613727</id>
                <element-id type="integer">3039</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">613728</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">613729</id>
                <element-id type="integer">8436</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">613730</id>
                <element-id type="integer">64</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">153833</id>
                <protein-complex-id type="integer">9669</protein-complex-id>
                <enzyme-class>2.7.8.5</enzyme-class>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
          <reaction>
            <id type="integer">163464</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R163464</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">613731</id>
                <element-id type="integer">8436</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">613732</id>
                <element-id type="integer">1420</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">613733</id>
                <element-id type="integer">6626</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">613734</id>
                <element-id type="integer">1104</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">153834</id>
                <protein-complex-id type="integer">9670</protein-complex-id>
                <enzyme-class nil="true"/>
              </reaction-enzyme>
            </reaction-enzymes>
          </reaction>
          <reaction>
            <id type="integer">163486</id>
            <spontaneous type="boolean" nil="true"/>
            <pwr-id>PW_R163486</pwr-id>
            <direction>Right</direction>
            <reaction-left-elements>
              <reaction-left-element>
                <id type="integer">613819</id>
                <element-id type="integer">6626</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">613820</id>
                <element-id type="integer">99574</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">613821</id>
                <element-id type="integer">101498</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">613822</id>
                <element-id type="integer">64</element-id>
                <stoichiometry type="integer">1</stoichiometry>
                <element-type>Compound</element-type>
                <currency type="boolean">false</currency>
              </reaction-right-element>
            </reaction-right-elements>
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