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CHEBI:17553 - O-phosphoethanolamine

ChEBI IDCHEBI:17553
ChEBI NameO-phosphoethanolamine
Stars
ASCII NameO-phosphoethanolamine
DefinitionThe ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. This phosphomonoester shows strong structural similarity to the inhibitory neurotransmitter GABA, and is decreased in post-mortem Alzheimer's disease brain.
Secondary ChEBI IDsCHEBI:4881, CHEBI:12694, CHEBI:14224, CHEBI:14814, CHEBI:23980, CHEBI:44681
Last Modified9 June 2025
DownloadsMolfile
FormulaC2H8NO4P
Net Charge0
Average Mass141.063
Monoisotopic Mass141.01909
SMILESNCCOP(=O)(O)O
InChIInChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)
InChIKeySUHOOTKUPISOBE-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
algal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
ChEBI Ontology
Outgoing Relation(s)
O-phosphoethanolamine (CHEBI:17553) has role algal metabolite (CHEBI:84735)
O-phosphoethanolamine (CHEBI:17553) has role human metabolite (CHEBI:77746)
O-phosphoethanolamine (CHEBI:17553) has role mouse metabolite (CHEBI:75771)
O-phosphoethanolamine (CHEBI:17553) is a phosphoethanolamine (CHEBI:36711)
O-phosphoethanolamine (CHEBI:17553) is a primary amino compound (CHEBI:50994)
O-phosphoethanolamine (CHEBI:17553) is conjugate acid of O-phosphonatoethanaminium(1−) (CHEBI:58190)
Incoming Relation(s)
N-acylethanolamine phosphate (CHEBI:145538) has functional parent O-phosphoethanolamine (CHEBI:17553)
venerose (CHEBI:234415) has functional parent O-phosphoethanolamine (CHEBI:17553)
O-phosphonatoethanaminium(1−) (CHEBI:58190) is conjugate base of O-phosphoethanolamine (CHEBI:17553)
IUPAC Name 
2-aminoethyl dihydrogen phosphate
Synonyms  Source
Ethanolamine phosphateKEGG COMPOUND
O-PhosphorylethanolamineKEGG COMPOUND
PhosphoethanolamineKEGG COMPOUND
O-PhosphoethanolamineKEGG COMPOUND
ethanolamine O-phosphateNIST Chemistry WebBook
mono(2-aminoethyl) phosphateChemIDplus
Manual XrefsDatabases
C00346KEGG COMPOUND
OPEPDBeChem
PHOSPHORYL-ETHANOLAMINEMetaCyc
DB01738DrugBank
Registry NumbersSources
Gmelin:663022Gmelin
Reaxys:1758916Reaxys
CAS:1071-23-4KEGG COMPOUND
CAS:1071-23-4ChemIDplus
CAS:1071-23-4NIST Chemistry WebBook
Citations