<?xml version="1.0" encoding="UTF-8"?>
<super-pathway-visualization>
  <named-for-id type="integer">16457</named-for-id>
  <named-for-type>Pathway</named-for-type>
  <cached-name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</cached-name>
  <cached-description>Phosphatidylethanolamines (PE) are a class of phospholipids that incorporate a phosphoric acid headgroup into a diacylglycerol backbone. They are the second most abundant phospholipid in eukaryotic cell membranes, and contrary to phosphatidylcholine, it is concentrated with phosphatidylserine in the cell membrane's inner leaflet. In Homo sapiens, there exist two phosphatidylethanolamine biosynthesis pathways. In the visualization, all enzymes that are dark green in colour are membrane-localized. The first pathway synthesizes phosphatidylethanolamine from ethanolamine via the Kennedy pathway. First, the cytosol-localized enzyme choline/ethanolamine kinase catalyzes the conversion of choline into phosphocholine. Second, choline-phosphate cytidylyltransferase, localized to the endoplasmic reticulum membrane, catalyzes the conversion of phosphocholine to CDP-choline. Last, choline/ethanolaminephosphotransferase catalyzes phosphatidylcholine biosynthesis from CDP-choline. It requires either magnesium or manganese ions as cofactors. Phosphatidylethanolamine is also synthesized from phosphatidylserine at the mitochondrial inner membrane by phosphatidylserine decarboxylase. Phosphatidylserine, itself, is synthesized using a base-exchange reaction with phosphatidylcholine. This reaction is catalyzed by phosphatidylserine synthase which is located in the endoplasmic reticulum membrane.</cached-description>
  <cached-subject>Metabolic</cached-subject>
  <pw-id>PW016647</pw-id>
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    <pathway-visualization-context>
      <position>Center</position>
      <id>PathwayVisualizationContext16931</id>
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        <width type="integer">2100</width>
        <background-color>#000099</background-color>
        <id>PathwayVisualization16402</id>
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          <id type="integer">16457</id>
          <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
          <description>Phosphatidylethanolamines (PE) are a class of phospholipids that incorporate a phosphoric acid headgroup into a diacylglycerol backbone. They are the second most abundant phospholipid in eukaryotic cell membranes, and contrary to phosphatidylcholine, it is concentrated with phosphatidylserine in the cell membrane's inner leaflet. In Homo sapiens, there exist two phosphatidylethanolamine biosynthesis pathways. In the visualization, all enzymes that are dark green in colour are membrane-localized. The first pathway synthesizes phosphatidylethanolamine from ethanolamine via the Kennedy pathway. First, the cytosol-localized enzyme choline/ethanolamine kinase catalyzes the conversion of choline into phosphocholine. Second, choline-phosphate cytidylyltransferase, localized to the endoplasmic reticulum membrane, catalyzes the conversion of phosphocholine to CDP-choline. Last, choline/ethanolaminephosphotransferase catalyzes phosphatidylcholine biosynthesis from CDP-choline. It requires either magnesium or manganese ions as cofactors. Phosphatidylethanolamine is also synthesized from phosphatidylserine at the mitochondrial inner membrane by phosphatidylserine decarboxylase. Phosphatidylserine, itself, is synthesized using a base-exchange reaction with phosphatidylcholine. This reaction is catalyzed by phosphatidylserine synthase which is located in the endoplasmic reticulum membrane.</description>
          <subject>Metabolic</subject>
          <species-id type="integer">1</species-id>
          <sub-pathways>
            <sub-pathway>
              <id type="integer">22501</id>
              <reference-pathway-id type="integer">14883</reference-pathway-id>
              <altext>Phosphatidylcholine Biosynthesis</altext>
              <sub-pathway-type>SubPathway</sub-pathway-type>
              <sub-pathway-outputs>
                <sub-pathway-output>
                  <id type="integer">21570</id>
                  <element-id type="integer">4728</element-id>
                  <element-type>Compound</element-type>
                  <biological-state-id type="integer">49</biological-state-id>
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            </sub-pathway>
          </sub-pathways>
          <references>
            <reference>
              <id type="integer">20887</id>
              <pubmed-id>22791820</pubmed-id>
              <text>Alatorre-Cobos F, Cruz-Ramirez A, Hayden CA, Perez-Torres CA, Chauvin AL, Ibarra-Laclette E, Alva-Cortes E, Jorgensen RA, Herrera-Estrella L: Translational regulation of Arabidopsis XIPOTL1 is modulated by phosphocholine levels via the phylogenetically conserved upstream open reading frame 30. J Exp Bot. 2012 Sep;63(14):5203-21. doi: 10.1093/jxb/ers180. Epub 2012 Jul 12.</text>
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              <element-type>Pathway</element-type>
            </reference>
          </references>
          <references>
            <reference>
              <id type="integer">20888</id>
              <pubmed-id>10893425</pubmed-id>
              <text>Henneberry AL, Wistow G, McMaster CR: Cloning, genomic organization, and characterization of a human cholinephosphotransferase. J Biol Chem. 2000 Sep 22;275(38):29808-15. doi: 10.1074/jbc.M005786200.</text>
              <element-id type="integer">16457</element-id>
              <element-type>Pathway</element-type>
            </reference>
          </references>
          <references>
            <reference>
              <id type="integer">20889</id>
              <pubmed-id>19915674</pubmed-id>
              <text>Gallego-Ortega D, Ramirez de Molina A, Ramos MA, Valdes-Mora F, Barderas MG, Sarmentero-Estrada J, Lacal JC: Differential role of human choline kinase alpha and beta enzymes in lipid metabolism: implications in cancer onset and treatment. PLoS One. 2009 Nov 12;4(11):e7819. doi: 10.1371/journal.pone.0007819.</text>
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              <element-type>Pathway</element-type>
            </reference>
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            <name>Platelet </name>
            <ontology-id>CL:0000233</ontology-id>
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            <name>Hepatocyte</name>
            <ontology-id>CL:0000182</ontology-id>
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            <name>Neuron</name>
            <ontology-id>CL:0000540</ontology-id>
          </cell-type>
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            <name>Cardiomyocyte</name>
            <ontology-id>CL:0000746</ontology-id>
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            <name>Beta cell</name>
            <ontology-id>CL:0000639</ontology-id>
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            <name>Epithelial Cell</name>
            <ontology-id>CL:0000066</ontology-id>
          </cell-type>
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            <name>Astrocyte</name>
            <ontology-id>CL:0000127</ontology-id>
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            <name>Glial cell</name>
            <ontology-id>CL:0000125</ontology-id>
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            <name>Homo sapiens</name>
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            <classification>Eukaryote</classification>
            <common-name>Human</common-name>
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            <name>Arabidopsis thaliana</name>
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            <classification>Eukaryote</classification>
            <common-name>Thale cress</common-name>
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            <name>Mus musculus</name>
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            <classification>Eukaryote</classification>
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            <name>Bos taurus</name>
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            <classification>Eukaryote</classification>
            <common-name>Cattle</common-name>
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            <name>Caenorhabditis elegans</name>
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            <classification>Eukaryote</classification>
            <common-name>Roundworm</common-name>
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            <name>Rattus norvegicus</name>
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            <classification>Eukaryote</classification>
            <common-name>Rat</common-name>
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            <name>Drosophila melanogaster</name>
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            <classification>Eukaryote</classification>
            <common-name>Fruit fly</common-name>
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            <name>Schizosaccharomyces pombe</name>
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            <classification>Eukaryote</classification>
            <common-name></common-name>
          </species>
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            <name>Solanum lycopersicum</name>
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            <classification>Eukaryote</classification>
            <common-name>Tomato</common-name>
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            <name>Saccharomyces cerevisiae</name>
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            <common-name>Yeast</common-name>
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            <common-name>African clawed frog</common-name>
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            <common-name>Deep sea mussel</common-name>
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            <name>Pseudomonas aeruginosa</name>
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            <name>Spathaspora passalidarum</name>
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            <common-name>Spathaspora passalidarum</common-name>
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            <classification>Eukaryote</classification>
            <common-name>Sitka spruce</common-name>
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            <name>Ethanolamine</name>
            <hmdb-id>HMDB0000149</hmdb-id>
            <description>Ethanolamine is a viscous, hygroscopic amino alcohol with an ammoniacal odor. It is widely distributed in biological tissue and is a component of lecithin. It is used as a surfactant, fluorometric reagent, and to remove CO2 and H2S from natural gas and other gases.</description>
            <cas>141-43-5</cas>
            <kegg-id>C00189</kegg-id>
            <pubchem-cid>700</pubchem-cid>
            <chebi-id>16000</chebi-id>
            <biocyc-id>ETHANOL-AMINE</biocyc-id>
            <chemspider-id>13835336</chemspider-id>
            <drugbank-id>DB03994</drugbank-id>
            <moldb-smiles>NCCO</moldb-smiles>
            <moldb-formula>C2H7NO</moldb-formula>
            <moldb-inchi>InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2</moldb-inchi>
            <moldb-inchikey>HZAXFHJVJLSVMW-UHFFFAOYSA-N</moldb-inchikey>
            <moldb-iupac>2-aminoethan-1-ol</moldb-iupac>
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            <foodb-id>FDB000769</foodb-id>
            <synonyms>1-amino-2-hydroxyethane;2-amino-1-ethanol;2-aminoethanol;2-aminoethyl alcohol;2-ethanolamine;2-hydroxyethanamine;2-hydroxyethylamine;Aethanolamin;Aminoethanol;Colamine;Envision conditioner pdd 9020;Ethanolamine;Ethylolamine;Glycinol;H-glycinol;Mea;Monoaethanolamin;Monoethanolamine;Olamine;B-aminoethanol;B-aminoethyl alcohol;B-ethanolamine;B-hydroxyethylamine;Beta-aminoethanol;Beta-aminoethyl alcohol;Beta-ethanolamine;Beta-hydroxyethylamine;Eta;2-amino-ethanol;2-aminoethan-1-ol;Hea;β-aminoethanol;β-aminoethyl alcohol;β-ethanolamine;β-hydroxyethylamine</synonyms>
            <pwc-id>PW_C000096</pwc-id>
            <short-name>ETA</short-name>
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            <name>Adenosine triphosphate</name>
            <hmdb-id>HMDB0000538</hmdb-id>
            <description>Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).</description>
            <cas>56-65-5</cas>
            <kegg-id>C00002</kegg-id>
            <pubchem-cid>5957</pubchem-cid>
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            <drugbank-id>DB00171</drugbank-id>
            <moldb-smiles>NC1=NC=NC2=C1N=CN2[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>C10H16N5O13P3</moldb-formula>
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            <moldb-iupac>({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</moldb-iupac>
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            <moldb-mono-mass>506.995745159</moldb-mono-mass>
            <moldb-alogps-logs>-2.05</moldb-alogps-logs>
            <moldb-donor-count>7</moldb-donor-count>
            <moldb-traditional-iupac>adenosine triphosphate</moldb-traditional-iupac>
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            <drugbank-metabolite-id nil="true"/>
            <foodb-id>FDB021813</foodb-id>
            <synonyms>5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid</synonyms>
            <pwc-id>PW_C000414</pwc-id>
            <short-name>ATP</short-name>
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            <name>O-Phosphoethanolamine</name>
            <hmdb-id>HMDB0000224</hmdb-id>
            <description>Phosphoethanolamine (PE) is a phosphomonoester metabolite of the phospholipid metabolism. PE is a precursor of phospholipid synthesis and a product of phospholipid breakdown. Phosphomonoesters are present at much higher levels in brain than in other organs. In developing brain, phosphomonoesters are normally elevated during the period of neuritic proliferation. This also coincides with the occurrence of normal programmed cell death and synaptic pruning in developing brain. These findings are consistent with the role of phosphomonoesters in membrane biosynthesis. PE shows a strong structural similarity to the inhibitory neurotransmitter, GABA, and the GABAB receptor partial agonist, 3-amino-propylphosphonic acid. PE is a phosphomonoester which is decreased in post-mortem Alzheimer's disease (AD) brain. (PMID: 7791524, 8588821, 11566853).</description>
            <cas>1071-23-4</cas>
            <kegg-id>C00346</kegg-id>
            <pubchem-cid>1015</pubchem-cid>
            <chebi-id>17553</chebi-id>
            <biocyc-id>PHOSPHORYL-ETHANOLAMINE</biocyc-id>
            <chemspider-id>990</chemspider-id>
            <drugbank-id nil="true"/>
            <moldb-smiles>NCCOP(O)(O)=O</moldb-smiles>
            <moldb-formula>C2H8NO4P</moldb-formula>
            <moldb-inchi>InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)</moldb-inchi>
            <moldb-inchikey>SUHOOTKUPISOBE-UHFFFAOYSA-N</moldb-inchikey>
            <moldb-iupac>(2-aminoethoxy)phosphonic acid</moldb-iupac>
            <moldb-average-mass>141.063</moldb-average-mass>
            <moldb-mono-mass>141.019094261</moldb-mono-mass>
            <moldb-alogps-logs>-0.74</moldb-alogps-logs>
            <moldb-donor-count>3</moldb-donor-count>
            <moldb-traditional-iupac>phosphorylethanolamine</moldb-traditional-iupac>
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            <drugbank-metabolite-id nil="true"/>
            <foodb-id>FDB021911</foodb-id>
            <synonyms>2-amino-ethanol dihydrogen phosphate;2-amino-ethanol dihydrogen phosphate (ester);2-amino-ethanol phosphate;2-aminoethanol o-phosphate;2-aminoethyl dihydrogen phosphate;2-aminoethyl dihydrogen phosphate (acd/name 4.0);2-aminoethyl phosphate;Colamine acid phosphate;Colamine phosphate;Colamine phosphoric acid;Colaminephosphoric acid;Colaminphosphoric acid;Eap;Ethanolamine o-phosphate;Ethanolamine acid phosphate;Ethanolamine phosphate;Mono(2-aminoethyl) phosphate;Monoaminoethyl phosphate;O-phosphocolamine;O-phosphoethanolamine;O-phosphorylethanolamine;Ope;Petn;Phosphoethanolamine;Phosphonoethanolamine;Phosphoric acid 2-aminoethyl phenyl ester;Phosphoryethanolamine;Phosphorylethanolamine;Pe;Pea;Phosphoryl-ethanolamine;2-amino-ethanol dihydrogen phosphoric acid;2-aminoethyl dihydrogen phosphoric acid;2-amino-ethanol phosphoric acid;Colaminphosphate;Ethanolamine acid phosphoric acid;Ethanolamine o-phosphoric acid;Ethanolamine phosphoric acid;Mono(2-aminoethyl) phosphoric acid;Monoaminoethyl phosphoric acid;Phosphate 2-aminoethyl phenyl ester;Ethamp;O-phosphonatoethanaminium</synonyms>
            <pwc-id>PW_C000149</pwc-id>
            <short-name>Ethamp</short-name>
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            <name>Adenosine diphosphate</name>
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            <description>Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.</description>
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            <kegg-id>C00008</kegg-id>
            <pubchem-cid>6022</pubchem-cid>
            <chebi-id>16761</chebi-id>
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            <moldb-inchi>InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</moldb-inchi>
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            <moldb-iupac>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</moldb-iupac>
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            <moldb-alogps-logs>-2.12</moldb-alogps-logs>
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            <foodb-id>FDB021817</foodb-id>
            <synonyms>Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acid</synonyms>
            <pwc-id>PW_C001034</pwc-id>
            <short-name>ADP</short-name>
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                <id type="integer">128308</id>
                <biological-state-id type="integer">506</biological-state-id>
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                <id type="integer">128361</id>
                <biological-state-id type="integer">391</biological-state-id>
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                <biological-state-id type="integer">395</biological-state-id>
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                <id type="integer">140692</id>
                <biological-state-id type="integer">882</biological-state-id>
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                <id type="integer">140693</id>
                <biological-state-id type="integer">883</biological-state-id>
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                <biological-state-id type="integer">167</biological-state-id>
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                <id type="integer">140707</id>
                <biological-state-id type="integer">168</biological-state-id>
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                <id type="integer">140715</id>
                <biological-state-id type="integer">14</biological-state-id>
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                <id type="integer">140742</id>
                <biological-state-id type="integer">788</biological-state-id>
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                <biological-state-id type="integer">597</biological-state-id>
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                <id type="integer">140760</id>
                <biological-state-id type="integer">185</biological-state-id>
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          <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>
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                <id type="integer">427</id>
                <biological-state-id type="integer">23</biological-state-id>
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                <biological-state-id type="integer">8</biological-state-id>
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                <biological-state-id type="integer">2</biological-state-id>
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                <id type="integer">7593</id>
                <biological-state-id type="integer">160</biological-state-id>
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                <biological-state-id type="integer">195</biological-state-id>
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                <biological-state-id type="integer">213</biological-state-id>
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                <biological-state-id type="integer">164</biological-state-id>
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                <biological-state-id type="integer">288</biological-state-id>
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                <biological-state-id type="integer">121</biological-state-id>
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                <id type="integer">122212</id>
                <biological-state-id type="integer">124</biological-state-id>
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                <id type="integer">122983</id>
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                <id type="integer">125840</id>
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                <id type="integer">127935</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>OP(O)(=O)OP(O)(O)=O</moldb-smiles>
            <moldb-formula>H4O7P2</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)</moldb-inchi>
            <moldb-inchikey>XPPKVPWEQAFLFU-UHFFFAOYSA-N</moldb-inchikey>
            <moldb-iupac>(phosphonooxy)phosphonic acid</moldb-iupac>
            <moldb-average-mass>177.9751</moldb-average-mass>
            <moldb-mono-mass>177.943225506</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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                <biological-state-id type="integer">2</biological-state-id>
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                <biological-state-id type="integer">372</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">80417</id>
                <biological-state-id type="integer">170</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">85630</id>
                <biological-state-id type="integer">1</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94786</id>
                <biological-state-id type="integer">384</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94814</id>
                <biological-state-id type="integer">125</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94819</id>
                <biological-state-id type="integer">382</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">98678</id>
                <biological-state-id type="integer">223</biological-state-id>
              </element-state>
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                <id type="integer">110634</id>
                <biological-state-id type="integer">391</biological-state-id>
              </element-state>
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                <id type="integer">113270</id>
                <biological-state-id type="integer">395</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">113275</id>
                <biological-state-id type="integer">389</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115527</id>
                <biological-state-id type="integer">136</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115532</id>
                <biological-state-id type="integer">399</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">119934</id>
                <biological-state-id type="integer">122</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120017</id>
                <biological-state-id type="integer">124</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120032</id>
                <biological-state-id type="integer">406</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120330</id>
                <biological-state-id type="integer">410</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120936</id>
                <biological-state-id type="integer">407</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">121261</id>
                <biological-state-id type="integer">429</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">121341</id>
                <biological-state-id type="integer">121</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">121486</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122407</id>
                <biological-state-id type="integer">422</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122985</id>
                <biological-state-id type="integer">444</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">123502</id>
                <biological-state-id type="integer">119</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">123831</id>
                <biological-state-id type="integer">464</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">124044</id>
                <biological-state-id type="integer">398</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">124977</id>
                <biological-state-id type="integer">375</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125324</id>
                <biological-state-id type="integer">297</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125395</id>
                <biological-state-id type="integer">299</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125410</id>
                <biological-state-id type="integer">479</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125597</id>
                <biological-state-id type="integer">484</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125656</id>
                <biological-state-id type="integer">485</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125876</id>
                <biological-state-id type="integer">481</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126552</id>
                <biological-state-id type="integer">491</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126869</id>
                <biological-state-id type="integer">205</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126935</id>
                <biological-state-id type="integer">388</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126950</id>
                <biological-state-id type="integer">501</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">127337</id>
                <biological-state-id type="integer">206</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">128124</id>
                <biological-state-id type="integer">508</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">140772</id>
                <biological-state-id type="integer">891</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">1201</id>
            <name>CDP-ethanolamine</name>
            <hmdb-id>HMDB0001564</hmdb-id>
            <description>Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a beta-N1-glycosidic bond. CDP-Ethanolamine has the chemical formula C11H20N4O11P2, and an average molecular weight of 446.2442. CDP-Ethanolamine is involved in multiple pathways, some of which are Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) Pathway, Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)) Pathway, Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0) Pathway, and Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) Pathway.</description>
            <cas>3036-18-8</cas>
            <kegg-id>C00570</kegg-id>
            <pubchem-cid>123727</pubchem-cid>
            <chebi-id>16732</chebi-id>
            <biocyc-id>CDP-ETHANOLAMINE</biocyc-id>
            <chemspider-id>110296</chemspider-id>
            <drugbank-id nil="true"/>
            <moldb-smiles>NCCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O</moldb-smiles>
            <moldb-formula>C11H20N4O11P2</moldb-formula>
            <moldb-inchi>InChI=1S/C11H20N4O11P2/c12-2-4-23-27(19,20)26-28(21,22)24-5-6-8(16)9(17)10(25-6)15-3-1-7(13)14-11(15)18/h1,3,6,8-10,16-17H,2,4-5,12H2,(H,19,20)(H,21,22)(H2,13,14,18)/t6-,8-,9-,10-/m1/s1</moldb-inchi>
            <moldb-inchikey>WVIMUEUQJFPNDK-PEBGCTIMSA-N</moldb-inchikey>
            <moldb-iupac>(2-aminoethoxy)[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid</moldb-iupac>
            <moldb-average-mass>446.2442</moldb-average-mass>
            <moldb-mono-mass>446.060380526</moldb-mono-mass>
            <moldb-alogps-logs>-1.53</moldb-alogps-logs>
            <moldb-donor-count>7</moldb-donor-count>
            <moldb-traditional-iupac>2-aminoethoxy({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)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>FDB022691</foodb-id>
            <synonyms>Cdp ethanolamine;Cdp-ethanolamine;Cdpethanolamine;Cytidine diphosphate ethanolamine;Cytidine 5'-(trihydrogen diphosphate), p'-(2-aminoethyl) ester</synonyms>
            <pwc-id>PW_C001201</pwc-id>
            <short-name>C-Etala</short-name>
            <element-states>
              <element-state>
                <id type="integer">3384</id>
                <biological-state-id type="integer">18</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">15290</id>
                <biological-state-id type="integer">288</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">15343</id>
                <biological-state-id type="integer">22</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">40895</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">78571</id>
                <biological-state-id type="integer">130</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79966</id>
                <biological-state-id type="integer">329</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79978</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94820</id>
                <biological-state-id type="integer">382</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94856</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">113276</id>
                <biological-state-id type="integer">389</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115533</id>
                <biological-state-id type="integer">399</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115749</id>
                <biological-state-id type="integer">398</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122603</id>
                <biological-state-id type="integer">125</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">125175</id>
                <biological-state-id type="integer">136</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126750</id>
                <biological-state-id type="integer">300</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">128344</id>
                <biological-state-id type="integer">395</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">4728</id>
            <name>PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
            <hmdb-id>HMDB0008680</hmdb-id>
            <description>PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines 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. PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of two chains of docosapentaenoic acid at the C-1 and C-2 positions. The docosapentaenoic acid moieties are derived from animal fats and brain. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.</description>
            <cas nil="true"/>
            <kegg-id>C00157</kegg-id>
            <pubchem-cid>53479323</pubchem-cid>
            <chebi-id nil="true"/>
            <biocyc-id> PHOSPHATIDYLCHOLINE</biocyc-id>
            <chemspider-id>24767341</chemspider-id>
            <drugbank-id nil="true"/>
            <moldb-smiles>CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC</moldb-smiles>
            <moldb-formula>C52H84NO8P</moldb-formula>
            <moldb-inchi>InChI=1S/C52H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-51(54)58-48-50(49-60-62(56,57)59-47-46-53(3,4)5)61-52(55)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h14-17,20-23,26-29,32-35,38-41,50H,6-13,18-19,24-25,30-31,36-37,42-49H2,1-5H3/b16-14-,17-15-,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-,40-38-,41-39-/t50-/m1/s1</moldb-inchi>
            <moldb-inchikey>XEIXOZPOEUOVNQ-FYOVADIISA-N</moldb-inchikey>
            <moldb-iupac>(2-{[(2R)-2,3-bis[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium</moldb-iupac>
            <moldb-average-mass>882.199</moldb-average-mass>
            <moldb-mono-mass>881.593455181</moldb-mono-mass>
            <moldb-alogps-logs>-7.41</moldb-alogps-logs>
            <moldb-donor-count>0</moldb-donor-count>
            <moldb-traditional-iupac>lecithin</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>C00157</foodb-id>
            <synonyms>1,2-didocosapentaenoyl-rac-glycero-3-phosphocholine;1,2-diosbondoyl-rac-glycero-3-phosphocholine;Gpcho(22:5/22:5);Gpcho(22:5n6/22:5n6);Gpcho(22:5w6/22:5w6);Gpcho(44:10);Lecithin;Pc(22:5/22:5);Pc(22:5n6/22:5n6);Pc(22:5w6/22:5w6);Pc(44:10);Phosphatidylcholine(22:5/22:5);Phosphatidylcholine(22:5n6/22:5n6);Phosphatidylcholine(22:5w6/22:5w6);Phosphatidylcholine(44:10)</synonyms>
            <pwc-id>PW_C004728</pwc-id>
            <short-name>Lecithi</short-name>
            <element-states>
              <element-state>
                <id type="integer">21140</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">21141</id>
                <biological-state-id type="integer">309</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">24989</id>
                <biological-state-id type="integer">18</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">92695</id>
                <biological-state-id type="integer">361</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">92696</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">108471</id>
                <biological-state-id type="integer">386</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">108472</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120177</id>
                <biological-state-id type="integer">401</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120178</id>
                <biological-state-id type="integer">398</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">120</id>
            <name>L-Serine</name>
            <hmdb-id>HMDB0000187</hmdb-id>
            <description>Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. (http://www.dcnutrition.com/AminoAcids/) L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373).</description>
            <cas>56-45-1</cas>
            <kegg-id>C00065</kegg-id>
            <pubchem-cid>5951</pubchem-cid>
            <chebi-id>17115</chebi-id>
            <biocyc-id>SER</biocyc-id>
            <chemspider-id>5736</chemspider-id>
            <drugbank-id>DB00133</drugbank-id>
            <moldb-smiles>N[C@@H](CO)C(O)=O</moldb-smiles>
            <moldb-formula>C3H7NO3</moldb-formula>
            <moldb-inchi>InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1</moldb-inchi>
            <moldb-inchikey>MTCFGRXMJLQNBG-REOHCLBHSA-N</moldb-inchikey>
            <moldb-iupac>(2S)-2-amino-3-hydroxypropanoic acid</moldb-iupac>
            <moldb-average-mass>105.0926</moldb-average-mass>
            <moldb-mono-mass>105.042593095</moldb-mono-mass>
            <moldb-alogps-logs>0.66</moldb-alogps-logs>
            <moldb-donor-count>3</moldb-donor-count>
            <moldb-traditional-iupac>L-serine</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>FDB012739</foodb-id>
            <synonyms>(-)-serine;(s)-2-amino-3-hydroxypropanoate;(s)-2-amino-3-hydroxypropanoic acid;(s)-2-amino-3-hydroxy-propanoate;(s)-2-amino-3-hydroxy-propanoic acid;(s)-serine;(s)-a-amino-b-hydroxypropionate;(s)-a-amino-b-hydroxypropionic acid;(s)-alpha-amino-beta-hydroxypropionate;(s)-alpha-amino-beta-hydroxypropionic acid;(s)-b-amino-3-hydroxypropionate;(s)-b-amino-3-hydroxypropionic acid;(s)-beta-amino-3-hydroxypropionate;(s)-beta-amino-3-hydroxypropionic acid;2-amino-3-hydroxypropanoate;2-amino-3-hydroxypropanoic acid;3-hydroxy-l-alanine;L-(-)-serine;L-3-hydroxy-2-aminopropionate;L-3-hydroxy-2-aminopropionic acid;L-3-hydroxy-alanine;L-ser;Serine;B-hydroxy-l-alanine;Beta-hydroxy-l-alanine;Beta-hydroxyalanine;(2s)-2-amino-3-hydroxypropanoic acid;(s)-(-)-serine;L-2-amino-3-hydroxypropionic acid;L-serin;S;Ser;(2s)-2-amino-3-hydroxypropanoate;(s)-α-amino-β-hydroxypropionate;(s)-α-amino-β-hydroxypropionic acid;β-hydroxy-l-alanine;B-hydroxyalanine;β-hydroxyalanine;L-2-amino-3-hydroxypropionate</synonyms>
            <pwc-id>PW_C000120</pwc-id>
            <short-name>Ser</short-name>
            <element-states>
              <element-state>
                <id type="integer">344</id>
                <biological-state-id type="integer">8</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">1810</id>
                <biological-state-id type="integer">2</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">2617</id>
                <biological-state-id type="integer">4</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">5642</id>
                <biological-state-id type="integer">107</biological-state-id>
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                <biological-state-id type="integer">160</biological-state-id>
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                <biological-state-id type="integer">224</biological-state-id>
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                <biological-state-id type="integer">249</biological-state-id>
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                <biological-state-id type="integer">151</biological-state-id>
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                <biological-state-id type="integer">49</biological-state-id>
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                <biological-state-id type="integer">318</biological-state-id>
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                <biological-state-id type="integer">315</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">77320</id>
                <biological-state-id type="integer">111</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">78088</id>
                <biological-state-id type="integer">133</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">78112</id>
                <biological-state-id type="integer">132</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">79979</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94858</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115752</id>
                <biological-state-id type="integer">398</biological-state-id>
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                <id type="integer">119924</id>
                <biological-state-id type="integer">122</biological-state-id>
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                <biological-state-id type="integer">124</biological-state-id>
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                <id type="integer">122136</id>
                <biological-state-id type="integer">406</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122718</id>
                <biological-state-id type="integer">135</biological-state-id>
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                <id type="integer">124667</id>
                <biological-state-id type="integer">118</biological-state-id>
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                <id type="integer">124688</id>
                <biological-state-id type="integer">120</biological-state-id>
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                <id type="integer">125314</id>
                <biological-state-id type="integer">297</biological-state-id>
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                <id type="integer">126209</id>
                <biological-state-id type="integer">299</biological-state-id>
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                <id type="integer">126293</id>
                <biological-state-id type="integer">479</biological-state-id>
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                <id type="integer">126860</id>
                <biological-state-id type="integer">205</biological-state-id>
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                <id type="integer">127856</id>
                <biological-state-id type="integer">501</biological-state-id>
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            <id type="integer">65</id>
            <name>Choline</name>
            <hmdb-id>HMDB0000097</hmdb-id>
            <description>Choline is a basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. Choline is now considered to be an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver, and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine into methionine). Lack of sufficient amounts of choline in the diet can lead to a fatty liver condition and general liver damage. This arises from the lack of VLDL, which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer.</description>
            <cas>62-49-7</cas>
            <kegg-id>C00114</kegg-id>
            <pubchem-cid>305</pubchem-cid>
            <chebi-id>15354</chebi-id>
            <biocyc-id>CPD-563</biocyc-id>
            <chemspider-id>299</chemspider-id>
            <drugbank-id>DB00122</drugbank-id>
            <moldb-smiles>C[N+](C)(C)CCO</moldb-smiles>
            <moldb-formula>C5H14NO</moldb-formula>
            <moldb-inchi>InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1</moldb-inchi>
            <moldb-inchikey>OEYIOHPDSNJKLS-UHFFFAOYSA-N</moldb-inchikey>
            <moldb-iupac>(2-hydroxyethyl)trimethylazanium</moldb-iupac>
            <moldb-average-mass>104.1708</moldb-average-mass>
            <moldb-mono-mass>104.107539075</moldb-mono-mass>
            <moldb-alogps-logs>-1.59</moldb-alogps-logs>
            <moldb-donor-count>1</moldb-donor-count>
            <moldb-traditional-iupac>choline</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>FDB000710</foodb-id>
            <synonyms>(2-hydroxyethyl)trimethyl ammonium;(2-hydroxyethyl)trimethylammonium;(beta-hydroxyethyl)trimethylammonium;2-hydroxy-n,n,n-trimethyl-ethanaminium;2-hydroxy-n,n,n-trimethylethanaminium;Bilineurine;Biocolina;Biocoline;Choline;Choline cation;Choline ion;Cholinum;Hepacholine;Hormocline;Lipotril;N,n,n-trimethylethanol-ammonium;N,n,n-trimethylethanolammonium;Neocolina;Paresan;N-trimethylethanolamine;Trimethylethanolamine</synonyms>
            <pwc-id>PW_C000065</pwc-id>
            <short-name>Choline</short-name>
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                <biological-state-id type="integer">3</biological-state-id>
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                <id type="integer">1497</id>
                <biological-state-id type="integer">14</biological-state-id>
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                <id type="integer">5612</id>
                <biological-state-id type="integer">119</biological-state-id>
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                <id type="integer">5619</id>
                <biological-state-id type="integer">137</biological-state-id>
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                <id type="integer">6849</id>
                <biological-state-id type="integer">7</biological-state-id>
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              <element-state>
                <id type="integer">12185</id>
                <biological-state-id type="integer">151</biological-state-id>
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                <id type="integer">12197</id>
                <biological-state-id type="integer">164</biological-state-id>
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                <id type="integer">12278</id>
                <biological-state-id type="integer">226</biological-state-id>
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                <id type="integer">15339</id>
                <biological-state-id type="integer">2</biological-state-id>
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                <biological-state-id type="integer">49</biological-state-id>
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                <id type="integer">77614</id>
                <biological-state-id type="integer">112</biological-state-id>
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                <id type="integer">77619</id>
                <biological-state-id type="integer">114</biological-state-id>
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                <id type="integer">78530</id>
                <biological-state-id type="integer">115</biological-state-id>
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                <id type="integer">79972</id>
                <biological-state-id type="integer">132</biological-state-id>
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                <id type="integer">79980</id>
                <biological-state-id type="integer">331</biological-state-id>
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                <id type="integer">94829</id>
                <biological-state-id type="integer">124</biological-state-id>
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                <id type="integer">94859</id>
                <biological-state-id type="integer">383</biological-state-id>
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                <id type="integer">113285</id>
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                <id type="integer">115541</id>
                <biological-state-id type="integer">118</biological-state-id>
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                <id type="integer">115753</id>
                <biological-state-id type="integer">398</biological-state-id>
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                <biological-state-id type="integer">409</biological-state-id>
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                <id type="integer">121306</id>
                <biological-state-id type="integer">405</biological-state-id>
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                <id type="integer">123876</id>
                <biological-state-id type="integer">376</biological-state-id>
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                <id type="integer">125987</id>
                <biological-state-id type="integer">478</biological-state-id>
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                <id type="integer">126471</id>
                <biological-state-id type="integer">481</biological-state-id>
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                <id type="integer">127440</id>
                <biological-state-id type="integer">209</biological-state-id>
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                <id type="integer">128040</id>
                <biological-state-id type="integer">206</biological-state-id>
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          <compound>
            <id type="integer">61271</id>
            <name>PS(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
            <hmdb-id>HMDB0112835</hmdb-id>
            <description>PS(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. 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. PS(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of osbond acid at the C-1 position and one chain of osbond acid at the C-2 position. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants, and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups (i.e. the phosphate moiety, the amino group and the carboxyl group). As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have a palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.</description>
            <cas nil="true"/>
            <kegg-id>C02737</kegg-id>
            <pubchem-cid>6323481</pubchem-cid>
            <chebi-id>18303</chebi-id>
            <biocyc-id>L-1-PHOSPHATIDYL-SERINE</biocyc-id>
            <chemspider-id>13628254</chemspider-id>
            <drugbank-id>DB00144</drugbank-id>
            <moldb-smiles>[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)C(O)=O</moldb-smiles>
            <moldb-formula>C50H78NO10P</moldb-formula>
            <moldb-inchi>InChI=1S/C50H78NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-48(52)58-43-46(44-59-62(56,57)60-45-47(51)50(54)55)61-49(53)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,35-38,46-47H,3-10,15-16,21-22,27-28,33-34,39-45,51H2,1-2H3,(H,54,55)(H,56,57)/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-,37-35-,38-36-/t46-,47+/m1/s1</moldb-inchi>
            <moldb-inchikey>UBMIAXKYLVVYDN-KOYGMSCBSA-N</moldb-inchikey>
            <moldb-iupac>(2S)-2-amino-3-({[(2R)-2,3-bis[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid</moldb-iupac>
            <moldb-average-mass>884.145</moldb-average-mass>
            <moldb-mono-mass>883.536334714</moldb-mono-mass>
            <moldb-alogps-logs>-7.11</moldb-alogps-logs>
            <moldb-donor-count>3</moldb-donor-count>
            <moldb-traditional-iupac>(2S)-2-amino-3-{[(2R)-2,3-bis[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propoxy(hydroxy)phosphoryl]oxy}propanoic 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-osbondoyl-2-osbondoyl-sn-glycero-3-phosphoserine ;PS(22:5/22:5) ;PS(22:5n6/22:5n6) ;PS(22:5w6/22:5w6) ;PS(44:10) ;Pser(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) ;Pser(22:5/22:5) ;Pser(22:5n6/22:5n6) ;Pser(22:5w6/22:5w6) ;Pser(44:10) ;Phosphatidylserine(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) ;Phosphatidylserine(22:5/22:5) ;Phosphatidylserine(22:5n6/22:5n6) ;Phosphatidylserine(22:5w6/22:5w6) ;Phosphatidylserine(44:10)</synonyms>
            <pwc-id>PW_C061271</pwc-id>
            <short-name>PS(44:1</short-name>
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                <id type="integer">21142</id>
                <biological-state-id type="integer">309</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">24990</id>
                <biological-state-id type="integer">49</biological-state-id>
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                <id type="integer">24991</id>
                <biological-state-id type="integer">17</biological-state-id>
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                <id type="integer">92692</id>
                <biological-state-id type="integer">134</biological-state-id>
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                <id type="integer">94214</id>
                <biological-state-id type="integer">331</biological-state-id>
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              <element-state>
                <id type="integer">108468</id>
                <biological-state-id type="integer">384</biological-state-id>
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              <element-state>
                <id type="integer">110837</id>
                <biological-state-id type="integer">383</biological-state-id>
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              <element-state>
                <id type="integer">120153</id>
                <biological-state-id type="integer">121</biological-state-id>
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              <element-state>
                <id type="integer">128822</id>
                <biological-state-id type="integer">398</biological-state-id>
              </element-state>
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          <compound>
            <id type="integer">5685</id>
            <name>PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
            <hmdb-id>HMDB0009637</hmdb-id>
            <description>PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines 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. PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of two chains of docosapentaenoic acid at the C-1 and C-2 positions. The docosapentaenoic acid moieties are derived from animal fats and brain. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.</description>
            <cas nil="true"/>
            <kegg-id>C00350</kegg-id>
            <pubchem-cid>53479933</pubchem-cid>
            <chebi-id nil="true"/>
            <biocyc-id>L-1-PHOSPHATIDYL-ETHANOLAMINE</biocyc-id>
            <chemspider-id>24769081</chemspider-id>
            <drugbank-id nil="true"/>
            <moldb-smiles>[H][C@@](COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(=O)OCCN)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC</moldb-smiles>
            <moldb-formula>C49H78NO8P</moldb-formula>
            <moldb-inchi>InChI=1S/C49H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-48(51)55-45-47(46-57-59(53,54)56-44-43-50)58-49(52)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,35-38,47H,3-10,15-16,21-22,27-28,33-34,39-46,50H2,1-2H3,(H,53,54)/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-,37-35-,38-36-/t47-/m1/s1</moldb-inchi>
            <moldb-inchikey>AUDAZOUFONZJII-SWUYWNKHSA-N</moldb-inchikey>
            <moldb-iupac>(2-aminoethoxy)[(2R)-2,3-bis[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propoxy]phosphinic acid</moldb-iupac>
            <moldb-average-mass>840.1193</moldb-average-mass>
            <moldb-mono-mass>839.546504989</moldb-mono-mass>
            <moldb-alogps-logs>-7.04</moldb-alogps-logs>
            <moldb-donor-count>2</moldb-donor-count>
            <moldb-traditional-iupac>2-aminoethoxy(2R)-2,3-bis[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propoxyphosphinic acid</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>C00350</foodb-id>
            <synonyms>1,2-didocosapentaenoyl-rac-glycero-3-phosphoethanolamine;1,2-diosbondoyl-rac-glycero-3-phosphoethanolamine;Gpetn(22:5/22:5);Gpetn(22:5n6/22:5n6);Gpetn(22:5w6/22:5w6);Gpetn(44:10);Pe(22:5/22:5);Pe(22:5n6/22:5n6);Pe(22:5w6/22:5w6);Pe(44:10);Phophatidylethanolamine(22:5/22:5);Phophatidylethanolamine(22:5n6/22:5n6);Phophatidylethanolamine(22:5w6/22:5w6);Phophatidylethanolamine(44:10)</synonyms>
            <pwc-id>PW_C005685</pwc-id>
            <short-name>PE44:10</short-name>
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              <element-state>
                <id type="integer">21138</id>
                <biological-state-id type="integer">49</biological-state-id>
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                <id type="integer">21139</id>
                <biological-state-id type="integer">309</biological-state-id>
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                <id type="integer">24992</id>
                <biological-state-id type="integer">17</biological-state-id>
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                <id type="integer">92689</id>
                <biological-state-id type="integer">331</biological-state-id>
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                <id type="integer">92690</id>
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                <biological-state-id type="integer">361</biological-state-id>
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                <id type="integer">108467</id>
                <biological-state-id type="integer">386</biological-state-id>
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                <id type="integer">120139</id>
                <biological-state-id type="integer">398</biological-state-id>
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                <id type="integer">120140</id>
                <biological-state-id type="integer">121</biological-state-id>
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                <id type="integer">120141</id>
                <biological-state-id type="integer">401</biological-state-id>
              </element-state>
            </element-states>
          </compound>
          <compound>
            <id type="integer">1316</id>
            <name>Carbon dioxide</name>
            <hmdb-id>HMDB0001967</hmdb-id>
            <description>Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.</description>
            <cas>124-38-9</cas>
            <kegg-id>C00011</kegg-id>
            <pubchem-cid>280</pubchem-cid>
            <chebi-id>16526</chebi-id>
            <biocyc-id></biocyc-id>
            <chemspider-id>274</chemspider-id>
            <drugbank-id></drugbank-id>
            <moldb-smiles>O=C=O</moldb-smiles>
            <moldb-formula>CO2</moldb-formula>
            <moldb-inchi>InChI=1S/CO2/c2-1-3</moldb-inchi>
            <moldb-inchikey>CURLTUGMZLYLDI-UHFFFAOYSA-N</moldb-inchikey>
            <moldb-iupac>methanedione</moldb-iupac>
            <moldb-average-mass>44.0095</moldb-average-mass>
            <moldb-mono-mass>43.989829244</moldb-mono-mass>
            <moldb-alogps-logs>0.63</moldb-alogps-logs>
            <moldb-donor-count>0</moldb-donor-count>
            <moldb-traditional-iupac>carbon dioxide</moldb-traditional-iupac>
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            <moldb-physiological-charge type="integer">0</moldb-physiological-charge>
            <drugbank-metabolite-id>DBMET00423</drugbank-metabolite-id>
            <foodb-id>FDB014084</foodb-id>
            <synonyms>Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744</synonyms>
            <pwc-id>PW_C001316</pwc-id>
            <short-name>CO2</short-name>
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            <name>DG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0)</name>
            <hmdb-id>HMDB0007728</hmdb-id>
            <description>DG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0), in particular, consists of two chains of docosapentaenoic acid at the C-1 and C-2 positions. The docosapentaenoic acid moieties are derived from animal fats and brain. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.</description>
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            <kegg-id>C00165</kegg-id>
            <pubchem-cid>53478481</pubchem-cid>
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            <moldb-smiles>[H][C@](CO)(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC</moldb-smiles>
            <moldb-formula>C47H72O5</moldb-formula>
            <moldb-inchi>InChI=1S/C47H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-46(49)51-44-45(43-48)52-47(50)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,35-38,45,48H,3-10,15-16,21-22,27-28,33-34,39-44H2,1-2H3/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-,37-35-,38-36-/t45-/m0/s1</moldb-inchi>
            <moldb-inchikey>WUVBCFAQSQUIDC-WGFPQIISSA-N</moldb-inchikey>
            <moldb-iupac>(2S)-1-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-hydroxypropan-2-yl (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoate</moldb-iupac>
            <moldb-average-mass>717.0716</moldb-average-mass>
            <moldb-mono-mass>716.537975414</moldb-mono-mass>
            <moldb-alogps-logs>-7.58</moldb-alogps-logs>
            <moldb-donor-count>1</moldb-donor-count>
            <moldb-traditional-iupac>diacylglycerol</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>FDB024921</foodb-id>
            <synonyms>1,2-didocosapentaenoyl-rac-glycerol;1,2-diosbondoyl-rac-glycerol;Dag(22:5/22:5);Dag(22:5n6/22:5n6);Dag(22:5w6/22:5w6);Dag(44:10);Dg(22:5/22:5);Dg(22:5n6/22:5n6);Dg(22:5w6/22:5w6);Dg(44:10);Diacylglycerol;Diacylglycerol(22:5/22:5);Diacylglycerol(22:5n6/22:5n6);Diacylglycerol(22:5w6/22:5w6);Diacylglycerol(44:10);Diglyceride</synonyms>
            <pwc-id>PW_C003779</pwc-id>
            <short-name>DG44:10</short-name>
            <element-states>
              <element-state>
                <id type="integer">21137</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">87372</id>
                <biological-state-id type="integer">331</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">101135</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120138</id>
                <biological-state-id type="integer">398</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>
            <element-states>
              <element-state>
                <id type="integer">1151</id>
                <biological-state-id type="integer">8</biological-state-id>
              </element-state>
              <element-state>
                <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>
              </element-state>
              <element-state>
                <id type="integer">5768</id>
                <biological-state-id type="integer">101</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">5802</id>
                <biological-state-id type="integer">108</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">7079</id>
                <biological-state-id type="integer">188</biological-state-id>
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              <element-state>
                <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>
              </element-state>
              <element-state>
                <id type="integer">12196</id>
                <biological-state-id type="integer">164</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">12210</id>
                <biological-state-id type="integer">151</biological-state-id>
              </element-state>
              <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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              <element-state>
                <id type="integer">34815</id>
                <biological-state-id type="integer">17</biological-state-id>
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              <element-state>
                <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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                <id type="integer">78488</id>
                <biological-state-id type="integer">115</biological-state-id>
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                <id type="integer">78573</id>
                <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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              <element-state>
                <id type="integer">79953</id>
                <biological-state-id type="integer">134</biological-state-id>
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              <element-state>
                <id type="integer">79969</id>
                <biological-state-id type="integer">331</biological-state-id>
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              <element-state>
                <id type="integer">80421</id>
                <biological-state-id type="integer">170</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94791</id>
                <biological-state-id type="integer">384</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">94821</id>
                <biological-state-id type="integer">383</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">98680</id>
                <biological-state-id type="integer">223</biological-state-id>
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              <element-state>
                <id type="integer">110637</id>
                <biological-state-id type="integer">391</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">113277</id>
                <biological-state-id type="integer">390</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">115535</id>
                <biological-state-id type="integer">398</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">120855</id>
                <biological-state-id type="integer">122</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">121346</id>
                <biological-state-id type="integer">121</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122216</id>
                <biological-state-id type="integer">124</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122487</id>
                <biological-state-id type="integer">405</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">122605</id>
                <biological-state-id type="integer">125</biological-state-id>
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                <id type="integer">123435</id>
                <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>
              </element-state>
              <element-state>
                <id type="integer">125841</id>
                <biological-state-id type="integer">297</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126378</id>
                <biological-state-id type="integer">299</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126641</id>
                <biological-state-id type="integer">478</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">126752</id>
                <biological-state-id type="integer">300</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">127293</id>
                <biological-state-id type="integer">205</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">127940</id>
                <biological-state-id type="integer">388</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">128217</id>
                <biological-state-id type="integer">209</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">128346</id>
                <biological-state-id type="integer">395</biological-state-id>
              </element-state>
            </element-states>
          </compound>
        </compounds>
        <element-collections>
        </element-collections>
        <nucleic-acids>
        </nucleic-acids>
        <proteins>
          <protein>
            <id type="integer">11846</id>
            <name>Choline kinase alpha</name>
            <uniprot-id>P35790</uniprot-id>
            <description>Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.</description>
            <hmdbp-id>HMDBP00778</hmdbp-id>
            <gene-name>CHKA</gene-name>
            <locus>11q13.2</locus>
            <drugbank-id nil="true"/>
            <genbank-id>BC036471</genbank-id>
            <species-id type="integer">1</species-id>
            <ec-numbers>2.7.1.32;2.7.1.82</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">15351</id>
                <biological-state-id type="integer">2</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">138451</id>
                <biological-state-id type="integer">160</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">697</id>
            <name>Ethanolamine-phosphate cytidylyltransferase</name>
            <uniprot-id>Q99447</uniprot-id>
            <description>Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine.
</description>
            <hmdbp-id>HMDBP00738</hmdbp-id>
            <gene-name>PCYT2</gene-name>
            <locus>17q25.3</locus>
            <drugbank-id nil="true"/>
            <genbank-id>CH471099</genbank-id>
            <species-id type="integer">1</species-id>
            <ec-numbers>2.7.7.14</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">4129</id>
                <biological-state-id type="integer">8</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">15370</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
            </element-states>
          </protein>
          <protein>
            <id type="integer">11850</id>
            <name>Phosphatidylserine synthase 1</name>
            <uniprot-id>P48651</uniprot-id>
            <description>Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine.</description>
            <hmdbp-id>HMDBP02190</hmdbp-id>
            <gene-name>PTDSS1</gene-name>
            <locus>8q22</locus>
            <drugbank-id nil="true"/>
            <genbank-id>BC004390</genbank-id>
            <species-id type="integer">1</species-id>
            <ec-numbers>2.7.8.29;2.7.8.-</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">15377</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">25476</id>
                <biological-state-id type="integer">18</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">138452</id>
                <biological-state-id type="integer">210</biological-state-id>
              </element-state>
            </element-states>
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          <protein>
            <id type="integer">1860</id>
            <name>Phosphatidylserine decarboxylase proenzyme</name>
            <uniprot-id>Q9UG56</uniprot-id>
            <description></description>
            <hmdbp-id>HMDBP02255</hmdbp-id>
            <gene-name>PISD</gene-name>
            <locus>22q12.2</locus>
            <drugbank-id nil="true"/>
            <genbank-id>BC009315</genbank-id>
            <species-id type="integer">1</species-id>
            <ec-numbers>4.1.1.65</ec-numbers>
            <synonyms nil="true"/>
            <element-states>
              <element-state>
                <id type="integer">1569</id>
                <biological-state-id type="integer">10</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">15371</id>
                <biological-state-id type="integer">17</biological-state-id>
              </element-state>
              <element-state>
                <id type="integer">138444</id>
                <biological-state-id type="integer">212</biological-state-id>
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            </element-states>
          </protein>
          <protein>
            <id type="integer">11849</id>
            <name>Choline/ethanolaminephosphotransferase 1</name>
            <uniprot-id>Q9Y6K0</uniprot-id>
            <description>Catalyzes both phosphatidylcholine and phosphatidylethanolamine biosynthesis from CDP-choline and CDP-ethanolamine, respectively. Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. Has a higher cholinephosphotransferase activity than ethanolaminephosphotransferase activity.</description>
            <hmdbp-id>HMDBP03349</hmdbp-id>
            <gene-name>CEPT1</gene-name>
            <locus>1p13.3</locus>
            <drugbank-id nil="true"/>
            <genbank-id>AF138862</genbank-id>
            <species-id type="integer">1</species-id>
            <ec-numbers>2.7.8.1;2.7.8.2</ec-numbers>
            <synonyms nil="true"/>
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                <biological-state-id type="integer">49</biological-state-id>
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              <element-state>
                <id type="integer">25475</id>
                <biological-state-id type="integer">18</biological-state-id>
              </element-state>
            </element-states>
          </protein>
        </proteins>
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          <protein-complex>
            <id type="integer">5654</id>
            <name>Choline/ethanolamine kinase</name>
            <species-id type="integer">1</species-id>
            <pwp-id>PW_P005654</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">13124</id>
                <protein-id type="integer">11846</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
            <element-states>
              <element-state>
                <id type="integer">15352</id>
                <biological-state-id type="integer">2</biological-state-id>
              </element-state>
            </element-states>
          </protein-complex>
          <protein-complex>
            <id type="integer">970</id>
            <name>Ethanolamine-phosphate cytidylyltransferase</name>
            <species-id type="integer">1</species-id>
            <pwp-id>PW_P000970</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">1096</id>
                <protein-id type="integer">697</protein-id>
                <stoichiometry type="integer">1</stoichiometry>
              </protein-complex-protein>
            </protein_complex-proteins>
          </protein-complex>
          <protein-complex>
            <id type="integer">5663</id>
            <name>Phosphatidylserine synthase</name>
            <species-id type="integer">1</species-id>
            <pwp-id>PW_P005663</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">13133</id>
                <protein-id type="integer">11850</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
            <element-states>
              <element-state>
                <id type="integer">15378</id>
                <biological-state-id type="integer">49</biological-state-id>
              </element-state>
            </element-states>
          </protein-complex>
          <protein-complex>
            <id type="integer">5662</id>
            <name>Phosphatidylserine decarboxylase</name>
            <species-id type="integer">1</species-id>
            <pwp-id>PW_P005662</pwp-id>
            <protein_complex-proteins>
              <protein-complex-protein>
                <id type="integer">13132</id>
                <protein-id type="integer">1860</protein-id>
                <stoichiometry type="integer" nil="true"/>
              </protein-complex-protein>
            </protein_complex-proteins>
            <element-states>
              <element-state>
                <id type="integer">15357</id>
                <biological-state-id type="integer">3</biological-state-id>
              </element-state>
            </element-states>
          </protein-complex>
          <protein-complex>
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            <name>Choline/ethanolaminephosphotransferase</name>
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