| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:07 -0700 |
| HMDB ID |
HMDB00224 |
| Secondary Accession Numbers |
|
| 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  , 8588821 , 11566853 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 2-Amino-Ethanol dihydrogen phosphate
- 2-Amino-Ethanol dihydrogen phosphate (ester)
- 2-Amino-Ethanol phosphate
- 2-Aminoethanol O-phosphate
- 2-Aminoethyl dihydrogen phosphate
- 2-Aminoethyl dihydrogen phosphate (ACD/Name 4.0)
- 2-Aminoethyl phosphate
- Colamine acid phosphate
- Colamine phosphate
- Colamine phosphoric acid
- Colaminephosphoric acid
- Colaminphosphoric acid
- EAP
- Ethanolamine acid phosphate
- Ethanolamine O-phosphate
- Ethanolamine phosphate
- Mono(2-aminoethyl) phosphate
- Monoaminoethyl phosphate
- O-Phosphocolamine
- O-Phosphoethanolamine
- O-Phosphorylethanolamine
- OPE
- PETN
- Phosphoethanolamine
- Phosphonoethanolamine
- Phosphoric acid 2-aminoethyl phenyl ester
- Phosphoryethanolamine
- 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 |
|
| 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 |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm
- Endoplasmic reticulum
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
|
| Tissue Location |
Not Available
|
| Pathways |
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
19 +/- 9.9 uM |
Newborn (0-30 days old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
4.0 +/- 2.0 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
6.0 +/- 1.1 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
6.30 (4.70-9.60) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
4.276 (1.644-6.908) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
8.2 +/- 2.0 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
11.3 (6.50-16.4) uM |
Adult (>18 years old) |
Both |
Brain injury |
Severe traumatic brain injury (TBI)
|
|
| 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 IDs |
None |
| External Links |
|---|
| DrugBank 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 |
| KEGG Compound ID |
C00346 |
| BioCyc ID |
PHOSPHORYL-ETHANOLAMINE |
| BiGG ID |
1485304 |
| Wikipedia Link |
Phosphoethanolamine |
| NuGOwiki Link |
HMDB00224 |
| Metagene Link |
HMDB00224 |
| METLIN ID |
5233 |
| PubChem Compound |
1015 |
| PDB ID |
OPE |
| ChEBI ID |
17553 |
| 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 |
- 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
- 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
|
