| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:27:00 UTC |
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| Update Date | 2020-06-04 20:35:20 UTC |
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| BMDB ID | BMDB0000224 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | O-Phosphoethanolamine |
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| Description | O-Phosphoethanolamine, also known as colamine phosphoric acid or ethanolamine phosphate, belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. O-Phosphoethanolamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. O-Phosphoethanolamine exists in all living species, ranging from bacteria to humans. O-Phosphoethanolamine is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2-Amino-ethanol dihydrogen phosphate | ChEBI | | 2-Amino-ethanol phosphate | ChEBI | | Colamine phosphate | ChEBI | | Colamine phosphoric acid | ChEBI | | Colaminphosphoric acid | ChEBI | | EAP | ChEBI | | Ethanolamine acid phosphate | ChEBI | | Ethanolamine O-phosphate | ChEBI | | Ethanolamine phosphate | ChEBI | | mono(2-Aminoethyl) phosphate | ChEBI | | Monoaminoethyl phosphate | ChEBI | | O-Phosphocolamine | ChEBI | | O-Phosphorylethanolamine | ChEBI | | OPE | ChEBI | | PE | ChEBI | | PEA | ChEBI | | PETN | ChEBI | | Phosphoethanolamine | ChEBI | | Phosphoric acid 2-aminoethyl phenyl ester | ChEBI | | Phosphoryl-ethanolamine | ChEBI | | 2-Amino-ethanol dihydrogen phosphoric acid | Generator | | 2-Amino-ethanol phosphoric acid | Generator | | Colaminphosphate | Generator | | Ethanolamine acid phosphoric acid | Generator | | Ethanolamine O-phosphoric acid | Generator | | Ethanolamine phosphoric acid | Generator | | mono(2-Aminoethyl) phosphoric acid | Generator | | Monoaminoethyl phosphoric acid | Generator | | Phosphate 2-aminoethyl phenyl ester | Generator | | Phosphonoethanolamine | HMDB | | 2-Amino-ethanol dihydrogen phosphate (ester) | HMDB | | 2-Aminoethanol O-phosphate | HMDB | | 2-Aminoethyl dihydrogen phosphate | HMDB | | 2-Aminoethyl dihydrogen phosphate (acd/name 4.0) | HMDB | | 2-Aminoethyl phosphate | HMDB | | Colamine acid phosphate | HMDB | | Colaminephosphoric acid | HMDB | | Ethamp | HMDB | | O-Phosphonatoethanaminium | HMDB | | Phosphoryethanolamine | HMDB | | Phosphorylethanolamine | HMDB | | Phosphorylethanolamine, 3H-labeled CPD | HMDB | | Phosphorylethanolamine magnesium (1:1) salt | HMDB | | Phosphorylethanolamine zinc salt | HMDB | | Phosphorylethanolamine, cobalt (2+) (1:1) salt | HMDB | | Calcium 2-aminoethanol phosphate | HMDB | | Phosphorylethanolamine ca (1:1) salt | HMDB |
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| Chemical Formula | C2H8NO4P |
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| Average Molecular Weight | 141.063 |
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| Monoisotopic Molecular Weight | 141.019094261 |
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| IUPAC Name | (2-aminoethoxy)phosphonic acid |
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| Traditional Name | phosphorylethanolamine |
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| CAS Registry Number | 1071-23-4 |
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| SMILES | NCCOP(O)(O)=O |
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| InChI Identifier | InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6) |
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| InChI Key | SUHOOTKUPISOBE-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Organic phosphoric acids and derivatives |
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| Sub Class | Phosphate esters |
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| Direct Parent | Phosphoethanolamines |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cytoplasm
- Endoplasmic reticulum
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| 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 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
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| Biospecimen Locations | - Liver
- Mammary Gland
- Milk
- Placenta
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 6934 +/- 1186 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0000224 |
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| DrugBank ID | DB01738 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB031115 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 990 |
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| KEGG Compound ID | C00346 |
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| BioCyc ID | PHOSPHORYL-ETHANOLAMINE |
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| BiGG ID | 1485304 |
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| Wikipedia Link | Phosphorylethanolamine |
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| METLIN ID | 5233 |
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| PubChem Compound | 1015 |
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| PDB ID | Not Available |
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| ChEBI ID | 17553 |
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| References |
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| 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. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
- Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
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