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Record Information
Version1.0
Creation Date2016-07-13 19:42:27 UTC
Update Date2016-07-20 20:25:06 UTC
LmdbLMDB00104
Secondary Accession NumbersNone
Metabolite Identification
Common NameO-Phosphoethanolamine
DescriptionPhosphoethanolamine (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 ).
Structure
Thumb
Synonyms
ValueSource
2-Amino-ethanol dihydrogen phosphateChEBI
2-Amino-ethanol phosphateChEBI
Colamine phosphateChEBI
Colamine phosphoric acidChEBI
Colaminphosphoric acidChEBI
EAPChEBI
Ethanolamine acid phosphateChEBI
Ethanolamine O-phosphateChEBI
Ethanolamine phosphateChEBI
mono(2-Aminoethyl) phosphateChEBI
Monoaminoethyl phosphateChEBI
O-PhosphocolamineChEBI
O-PhosphorylethanolamineChEBI
OPEChEBI
PEChEBI
PEAChEBI
PETNChEBI
PhosphoethanolamineChEBI
Phosphoric acid 2-aminoethyl phenyl esterChEBI
Phosphoryl-ethanolamineChEBI
2-Amino-ethanol dihydrogen phosphoric acidGenerator
2-Amino-ethanol phosphoric acidGenerator
ColaminphosphateGenerator
Ethanolamine acid phosphoric acidGenerator
Ethanolamine O-phosphoric acidGenerator
Ethanolamine phosphoric acidGenerator
mono(2-Aminoethyl) phosphoric acidGenerator
Monoaminoethyl phosphoric acidGenerator
Phosphate 2-aminoethyl phenyl esterGenerator
PhosphonoethanolamineHMDB
2-Amino-ethanol dihydrogen phosphate (ester)HMDB
2-Aminoethanol O-phosphateHMDB
2-Aminoethyl dihydrogen phosphateHMDB
2-Aminoethyl dihydrogen phosphate (acd/name 4.0)HMDB
2-Aminoethyl phosphateHMDB
Colamine acid phosphateHMDB
Colaminephosphoric acidHMDB
EthampHMDB
O-PhosphonatoethanaminiumHMDB
PhosphoryethanolamineHMDB
PhosphorylethanolamineHMDB
Phosphorylethanolamine, 3H-labeled CPDHMDB
Phosphorylethanolamine magnesium (1:1) saltHMDB
Phosphorylethanolamine zinc saltHMDB
Phosphorylethanolamine, cobalt (2+) (1:1) saltHMDB
Calcium 2-aminoethanol phosphateHMDB
Phosphorylethanolamine ca (1:1) saltHMDB
Chemical FormulaC2H8NO4P
Average Molecular Weight141.063
Monoisotopic Molecular Weight141.019094261
IUPAC Name(2-aminoethoxy)phosphonic acid
Traditional Namephosphorylethanolamine
CAS Registry Number1071-23-4
SMILES
NCCOP(O)(O)=O
InChI Identifier
InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)
InChI KeySUHOOTKUPISOBE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentPhosphoethanolamines
Alternative Parents
Substituents
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.5ALOGPS
logP-2.5ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)1.54ChemAxon
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.08 m³·mol⁻¹ChemAxon
Polarizability11.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0fki-0910000000-63541b89e6730018e48bSpectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0h9a-1921000000-3a1d4ab89b928259f71dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fki-0910000000-63541b89e6730018e48bSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h9a-1921000000-3a1d4ab89b928259f71dSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h9a-1921000000-3a1d4ab89b928259f71dSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h9a-1921000000-3a1d4ab89b928259f71dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fki-0911000000-7fc066f17e2ebf6c84f8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9100000000-543d2d90aa663406e999Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-2900000000-9cf72ee86018eb78504fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-169b03f94a9f53bd0de4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-199d7ab7a4aeb040674eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-f573b62dada3630598c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-38c04ce07a85a8db342cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-9100000000-b582c6b51602884756daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-2900000000-9cf72ee86018eb78504fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-169b03f94a9f53bd0de4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-199d7ab7a4aeb040674eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-f573b62dada3630598c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-38c04ce07a85a8db342cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9100000000-b582c6b51602884756daSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-9000000000-4335e927ba2537543f7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-9000000000-3e5f10c6e140e555b9feSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-db65ce46b55b09e54fd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-2fd2f3cd8548fd78801dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-f56d20ee0f56f087220dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-9000000000-d64f2b030ca512262fb1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9100000000-993b8efd11624567ec4bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-f2fd3c258685af07afb5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b479823e7c0ee6b5e03dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c4e1a40502d86192ed6bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-b5f55e00526c703b9bedSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-e5987c09032f652371caSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-42653da62fb10227ae1bSpectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-88dc3b66f275af50de34Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Follicular Fluid
  • Lung
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Follicular FluidDetected and Quantified22 +/- 2-42+/-4 uMNot AvailablePorcine details
Follicular FluidDetected and Quantified29 +/- 4-62+/-1 uMNot AvailablePorcine details
LungDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified7 +/- 1 uMNot AvailablePorcine details
DrugBank IDDB01738
HMDB IDHMDB0000224
FooDB IDFDB031115
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID1485304
BioCyc IDPHOSPHORYL-ETHANOLAMINE
METLIN ID5233
PDB IDNot Available
Wikipedia LinkPhosphorylethanolamine
Chemspider ID990
ChEBI ID17553
PubChem Compound ID1015
Kegg Compound IDC00346
YMDB IDYMDB00125
ECMDB IDECMDB21417
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Klunk WE, Debnath ML, McClure RJ, Pettegrew JW: Inactivity of phosphoethanolamine, an endogenous GABA analog decreased in Alzheimer's disease, at GABA binding sites. Life Sci. 1995;56(26):2377-83. [7791524 ]
  2. Klunk WE, McClure RJ, Xu CJ, Pettegrew JW: Structural determinants of activity at the GABAB receptor. A comparison of phosphoethanolamine and related GABA analogs. Mol Chem Neuropathol. 1995 Sep;26(1):15-30. [8588821 ]
  3. Li G, Foote C, Alexander S, Alexander H: Sphingosine-1-phosphate lyase has a central role in the development of Dictyostelium discoideum. Development. 2001 Sep;128(18):3473-83. [11566853 ]