Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:07 UTC
HMDB IDHMDB00224
Secondary Accession Numbers
  • HMDB12279
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
  1. 2-Amino-Ethanol dihydrogen phosphate
  2. 2-Amino-Ethanol dihydrogen phosphate (ester)
  3. 2-Amino-Ethanol phosphate
  4. 2-Aminoethanol O-phosphate
  5. 2-Aminoethyl dihydrogen phosphate
  6. 2-Aminoethyl dihydrogen phosphate (ACD/Name 4.0)
  7. 2-Aminoethyl phosphate
  8. Colamine acid phosphate
  9. Colamine phosphate
  10. Colamine phosphoric acid
  11. Colaminephosphoric acid
  12. Colaminphosphoric acid
  13. EAP
  14. Ethanolamine acid phosphate
  15. Ethanolamine O-phosphate
  16. Ethanolamine phosphate
  17. Mono(2-aminoethyl) phosphate
  18. Monoaminoethyl phosphate
  19. O-Phosphocolamine
  20. O-Phosphoethanolamine
  21. O-Phosphorylethanolamine
  22. OPE
  23. PETN
  24. Phosphoethanolamine
  25. Phosphonoethanolamine
  26. Phosphoric acid 2-aminoethyl phenyl ester
  27. Phosphoryethanolamine
  28. Phosphorylethanolamine
Chemical FormulaC2H8NO4P
Average Molecular Weight141.063
Monoisotopic Molecular Weight141.019094261
IUPAC Name(2-aminoethoxy)phosphonic acid
Traditional IUPAC Name2-aminoethoxyphosphonic acid
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
KingdomOrganic Compounds
Super ClassOrganophosphorus Compounds
ClassOrganic Phosphoric Acids and Derivatives
Sub ClassOrganophosphate Esters
Other Descriptors
  • Aliphatic Acyclic Compounds
  • phosphoethanolamine(ChEBI)
Substituents
  • Organic Hypophosphite
  • Organic Phosphite
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentPhosphoethanolamines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycerophospholipid metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point241 - 243 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility72 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility25.8 g/LALOGPS
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 area92.78ChemAxon
rotatable bond count3ChemAxon
refractivity27.08ChemAxon
polarizability11.12ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Sphingolipid MetabolismSMP00034map00500
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified19 +/- 9.9 uMNewborn (0-30 days old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified4.0 +/- 2.0 uMAdult (>18 years old)FemaleNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified6.0 +/- 1.1 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified6.30 (4.70-9.60) uMAdult (>18 years old)BothNormal
UrineDetected and Quantified4.276 (1.644-6.908) umol/mmol creatinineAdult (>18 years old)BothNormal
    UrineDetected and Quantified8.2 +/- 2.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scient...
    • West Cadwell...
    • Basel, Switz...
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReference
    Cerebrospinal Fluid (CSF)Detected and Quantified11.3 (6.50-16.4) uMAdult (>18 years old)BothCommentBrain injury
    Associated Disorders and Diseases
    Disease References
    Traumatic brain injury
    • Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. Pubmed: 15756940
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB021911
    KNApSAcK IDNot Available
    Chemspider ID990
    KEGG Compound IDC00346
    BioCyc IDPHOSPHORYL-ETHANOLAMINE
    BiGG ID1485304
    Wikipedia LinkPhosphoethanolamine
    NuGOwiki LinkHMDB00224
    Metagene LinkHMDB00224
    METLIN ID5233
    PubChem Compound1015
    PDB IDOPE
    ChEBI ID17553
    References
    Synthesis ReferenceMuller K; Schulz J; Oemus R Phosphoethanolamine--a substrate of alkaline phosphatase isolated from rat calvaria. Biomedica biochimica acta (1989), 48(8), 495-504.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
    2. Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. Pubmed: 15756940
    3. 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. Pubmed: 7791524
    4. 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. Pubmed: 8588821
    5. 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. Pubmed: 11566853

    Enzymes

    Gene Name:
    PCYT2
    Uniprot ID:
    Q99447
    Reactions
    Cytidine triphosphate + O-Phosphoethanolamine unknown Pyrophosphate + CDP-Ethanolaminedetails
    Gene Name:
    CHKB
    Uniprot ID:
    Q9Y259
    Reactions
    Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolaminedetails
    Gene Name:
    CHKA
    Uniprot ID:
    P35790
    Reactions
    Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolaminedetails
    Gene Name:
    ETNK1
    Uniprot ID:
    Q9HBU6
    Reactions
    Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolaminedetails
    Gene Name:
    SGPL1
    Uniprot ID:
    O95470
    Reactions
    Sphinganine 1-phosphate unknown O-Phosphoethanolamine + Palmitaldehydedetails
    Sphingosine 1-phosphate unknown O-Phosphoethanolamine + Hexadecenaldetails
    Gene Name:
    PHOSPHO1
    Uniprot ID:
    Q8TCT1
    Reactions
    O-Phosphoethanolamine + Water unknown Ethanolamine + Phosphoric aciddetails
    Gene Name:
    AGXT2L1
    Uniprot ID:
    Q8TBG4
    Reactions
    O-Phosphoethanolamine + Water unknown Acetaldehyde + Ammonia + Phosphoric aciddetails
    Gene Name:
    ETNK2
    Uniprot ID:
    Q9NVF9
    Reactions
    Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolaminedetails
    Gene Name:
    ENPP6
    Uniprot ID:
    Q6UWR7
    Reactions
    1-(1-Alkenyl)-sn-glycero-3-phosphoethanolamine + Water unknown 1-(1-Alkenyl)-sn-glycerol + O-Phosphoethanolaminedetails
    Gene Name:
    HRASLS2
    Uniprot ID:
    Q9NWW9
    Reactions
    Phosphatidylcholine + O-Phosphoethanolamine unknown 1-acylglycerophosphocholine + N-palmitoyl-phosphoethanolaminedetails