<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4460</id>
  <title>T3D4406</title>
  <common-name>O-Phosphoethanolamine</common-name>
  <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.  (A3481, A3482, A3483).</description>
  <cas>1071-23-4</cas>
  <pubchem-id>1015</pubchem-id>
  <chemical-formula>C2H8NO4P</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>241 - 243°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>72 mg/mL</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity nil="true"/>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T06:51:02Z</created-at>
  <updated-at type="dateTime">2026-05-14T17:14:42Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Phosphoethanolamine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C00346</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>17553</chebi-id>
  <biocyc-id>PHOSPHORYL-ETHANOLAMINE</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB01738</drugbank-id>
  <pdb-id>OPE</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins 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-average-mass type="decimal">141.063</moldb-average-mass>
  <moldb-mono-mass type="decimal">141.019094261</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp>-2.5</logp>
  <hmdb-id>HMDB00224</hmdb-id>
  <chembl-id>CHEMBL146972</chembl-id>
  <chemspider-id>990</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003366</chemdb-id>
  <dsstox-id>DTXSID5061453</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>(2-aminoethoxy)phosphonic acid</iupac>
  <moldb-polar-surface-area>92.77999999999999</moldb-polar-surface-area>
  <moldb-refractivity>27.084</moldb-refractivity>
  <moldb-polarizability>11.11675089618825</moldb-polarizability>
  <moldb-rotatable-bond-count>3</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>1.5391795005429323</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>10.017192603268537</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-1</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>-1.54</moldb-alogps-logp>
  <moldb-alogps-logs>-0.74</moldb-alogps-logs>
  <moldb-alogps-solubility>2.58e+01 g/l</moldb-alogps-solubility>
</compound>
