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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
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified19 +/- 9.9 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified4.0 +/- 2.0 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified6.0 +/- 1.1 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified6.30 (4.70-9.60) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.276 (1.644-6.908) umol/mmol creatinineAdult (>18 years old)BothNormal
    details
    UrineDetected and Quantified8.2 +/- 2.0 umol/mmol creatinineAdult (>18 years old)BothNormal
      • Geigy Scientific ...
      • West Cadwell, N.J...
      • Basel, Switzerlan...
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    Cerebrospinal Fluid (CSF)Detected and Quantified11.3 (6.50-16.4) uMAdult (>18 years old)Both
    Brain injury
    details
    Associated Disorders and Diseases
    Disease References
    Traumatic brain injury
    1. 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)Download (PDF)
    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

    General function:
    Involved in catalytic activity
    Specific function:
    Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine.
    Gene Name:
    PCYT2
    Uniprot ID:
    Q99447
    Molecular weight:
    35199.52
    Reactions
    Cytidine triphosphate + O-Phosphoethanolamine → Pyrophosphate + CDP-Ethanolaminedetails
    General function:
    Cell wall/membrane/envelope biogenesis
    Specific function:
    Has a key role in phospholipid biosynthesis. Catalyzes the first step in phosphatidylethanolamine biosynthesis. Phosphorylates ethanolamine, and can also act on choline (in vitro). Has higher activity with ethanolamine. May not significantly contribute to in vivo phosphatidylcholine biosynthesis.
    Gene Name:
    CHKB
    Uniprot ID:
    Q9Y259
    Molecular weight:
    45270.99
    Reactions
    Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
    General function:
    Cell wall/membrane/envelope biogenesis
    Specific function:
    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.
    Gene Name:
    CHKA
    Uniprot ID:
    P35790
    Molecular weight:
    52248.53
    Reactions
    Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
    General function:
    Cell wall/membrane/envelope biogenesis
    Specific function:
    Highly specific for ethanolamine phosphorylation. May be a rate-controlling step in phosphatidylethanolamine biosynthesis.
    Gene Name:
    ETNK1
    Uniprot ID:
    Q9HBU6
    Molecular weight:
    27994.955
    Reactions
    Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
    General function:
    Involved in carboxy-lyase activity
    Specific function:
    Cleaves phosphorylated sphingoid bases (PSBs), such as sphingosine-1-phosphate, into fatty aldehydes and phosphoethanolamine. Elevates stress-induced ceramide production and apoptosis.
    Gene Name:
    SGPL1
    Uniprot ID:
    O95470
    Molecular weight:
    63523.265
    Reactions
    Sphinganine 1-phosphate → O-Phosphoethanolamine + Palmitaldehydedetails
    Sphingosine 1-phosphate → O-Phosphoethanolamine + Hexadecenaldetails
    General function:
    Involved in phosphatase activity
    Specific function:
    Phosphatase that has a high activity toward phosphoethanolamine (PEA) and phosphocholine (PCho). Involved in the generation of inorganic phosphate for bone mineralization.
    Gene Name:
    PHOSPHO1
    Uniprot ID:
    Q8TCT1
    Molecular weight:
    32350.505
    Reactions
    O-Phosphoethanolamine + Water → Ethanolamine + Phosphoric aciddetails
    General function:
    Involved in transaminase activity
    Specific function:
    Catalyzes the pyridoxal-phosphate-dependent breakdown of phosphoethanolamine, converting it to ammonia, inorganic phosphate and acetaldehyde.
    Gene Name:
    AGXT2L1
    Uniprot ID:
    Q8TBG4
    Molecular weight:
    55039.64
    Reactions
    O-Phosphoethanolamine + Water → Acetaldehyde + Ammonia + Phosphoric aciddetails
    General function:
    Cell wall/membrane/envelope biogenesis
    Specific function:
    Highly specific for ethanolamine phosphorylation. Does not have choline kinase activity (By similarity).
    Gene Name:
    ETNK2
    Uniprot ID:
    Q9NVF9
    Molecular weight:
    44781.125
    Reactions
    Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
    General function:
    Involved in catalytic activity
    Specific function:
    Choline-specific glycerophosphodiester phosphodiesterase. The preferred substrate may be lysosphingomyelin (By similarity). Hydrolyzes lysophosphatidylcholine (LPC) to form monoacylglycerol and phosphorylcholine but not lysophosphatidic acid, showing it has a lysophospholipase C activity. Has a preference for LPC with short (12:0 and 14:0) or polyunsaturated (18:2 and 20:4) fatty acids. Also hydrolyzes glycerophosphorylcholine and sphingosylphosphorylcholine efficiently. Hydrolyzes the classical substrate for phospholipase C, p-nitrophenyl phosphorylcholine in vitro, while it does not hydrolyze the classical nucleotide phosphodiesterase substrate, p-nitrophenyl thymidine 5'-monophosphate. Does not hydrolyze diacyl phospholipids such as phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylglycerol and phosphatidic acid.
    Gene Name:
    ENPP6
    Uniprot ID:
    Q6UWR7
    Molecular weight:
    50240.625
    Reactions
    1-(1-Alkenyl)-sn-glycero-3-phosphoethanolamine + Water → 1-(1-Alkenyl)-sn-glycerol + O-Phosphoethanolaminedetails
    General function:
    Not Available
    Specific function:
    Exhibits PLA1/2 activity, catalyzing the calcium-independent hydrolysis of acyl groups in various phosphotidylcholines (PC) and phosphatidylethanolamine (PE). For most substrates, PLA1 activity is much higher than PLA2 activity. Catalyzes N-acylation of PE using both sn-1 and sn-2 palmitoyl groups of PC as acyl donor. Also catalyzes O-acylation converting lyso-PC into PC.
    Gene Name:
    HRASLS2
    Uniprot ID:
    Q9NWW9
    Molecular weight:
    17393.695
    Reactions
    Phosphatidylcholine + O-Phosphoethanolamine → 1-acylglycerophosphocholine + N-palmitoyl-phosphoethanolaminedetails