Human Metabolome Database Version 3.5

Showing metabocard for O-Phosphoethanolamine (HMDB00224)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:25:07 -0600
HMDB ID HMDB00224
Secondary Accession Numbers
  • HMDB12279
Metabolite Identification
Common Name O-Phosphoethanolamine
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. (PMID: 7791524 Link_out, 8588821 Link_out, 11566853 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C2H8NO4P
Average Molecular Weight 141.063
Monoisotopic Molecular Weight 141.019094261
IUPAC Name (2-aminoethoxy)phosphonic acid
Traditional IUPAC Name 2-aminoethoxyphosphonic acid
CAS Registry Number 1071-23-4
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 Key SUHOOTKUPISOBE-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organophosphorus Compounds
Class Organic Phosphoric Acids and Derivatives
Sub Class Organophosphate Esters
Other Descriptors
  • Aliphatic Acyclic Compounds
  • phosphoethanolamine(ChEBI)
Substituents
  • Organic Hypophosphite
  • Organic Phosphite
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Phosphoethanolamines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycerophospholipid metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 241 - 243 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 72 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 25.8 g/L ALOGPS
LogP -1.54 ALOGPS
LogP -2.5 ChemAxon
LogS -0.74 ALOGPS
pKa (strongest acidic) 1.54 ChemAxon
pKa (strongest basic) 10.02 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 92.78 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 27.08 ChemAxon
Polarizability 11.12 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Sphingolipid Metabolism SMP00034 map00500 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
19 +/- 9.9 uM Newborn (0-30 days old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
4.0 +/- 2.0 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
6.0 +/- 1.1 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
6.30 (4.70-9.60) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
4.276 (1.644-6.908) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
8.2 +/- 2.0 umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 11.3 (6.50-16.4) uM Adult (>18 years old) Both Comment Brain 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 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB021911
      KNApSAcK ID Not Available
      Chemspider ID 990 Link_out
      KEGG Compound ID C00346 Link_out
      BioCyc ID PHOSPHORYL-ETHANOLAMINE Link_out
      BiGG ID 1485304 Link_out
      Wikipedia Link Phosphoethanolamine Link_out
      NuGOwiki Link HMDB00224 Link_out
      Metagene Link HMDB00224 Link_out
      METLIN ID 5233 Link_out
      PubChem Compound 1015 Link_out
      PDB ID OPE Link_out
      ChEBI ID 17553 Link_out
      References
      Synthesis Reference Muller 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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: Ethanolamine-phosphate cytidylyltransferase
      Reactions:
      Cytidine triphosphate + O-Phosphoethanolamine unknown Pyrophosphate + CDP-Ethanolamine details
      Gene Name: PCYT2
      Uniprot ID: Q99447 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Choline/ethanolamine kinase
      Reactions:
      Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolamine details
      Gene Name: CHKB
      Uniprot ID: Q9Y259 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Choline kinase alpha
      Reactions:
      Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolamine details
      Gene Name: CHKA
      Uniprot ID: P35790 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ethanolamine kinase 1
      Reactions:
      Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolamine details
      Gene Name: ETNK1
      Uniprot ID: Q9HBU6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Sphingosine-1-phosphate lyase 1
      Reactions:
      Sphinganine 1-phosphate unknown O-Phosphoethanolamine + Palmitaldehyde details
      Sphingosine 1-phosphate unknown O-Phosphoethanolamine + Hexadecenal details
      Gene Name: SGPL1
      Uniprot ID: O95470 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Phosphoethanolamine/phosphocholine phosphatase
      Reactions:
      O-Phosphoethanolamine + Water unknown Ethanolamine + Phosphoric acid details
      Gene Name: PHOSPHO1
      Uniprot ID: Q8TCT1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ethanolamine-phosphate phospho-lyase
      Reactions:
      O-Phosphoethanolamine + Water unknown Acetaldehyde + Ammonia + Phosphoric acid details
      Gene Name: AGXT2L1
      Uniprot ID: Q8TBG4 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ethanolamine kinase 2
      Reactions:
      Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolamine details
      Gene Name: ETNK2
      Uniprot ID: Q9NVF9 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 6
      Reactions:
      1-(1-Alkenyl)-sn-glycero-3-phosphoethanolamine + Water unknown 1-(1-Alkenyl)-sn-glycerol + O-Phosphoethanolamine details
      Gene Name: ENPP6
      Uniprot ID: Q6UWR7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: HRAS-like suppressor 2
      Reactions:
      Phosphatidylcholine + O-Phosphoethanolamine unknown 1-acylglycerophosphocholine + N-palmitoyl-phosphoethanolamine details
      Gene Name: HRASLS2
      Uniprot ID: Q9NWW9 Link_out
      Protein Sequence: FASTA