| Record Information |
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| Version | 4.0 |
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| Status | Detected but not Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2020-02-26 21:21:52 UTC |
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| HMDB ID | HMDB0000114 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Glycerylphosphorylethanolamine |
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| Description | sn-glycero-3-phosphoethanolamine belongs to the class of organic compounds known as glycerophosphoethanolamines. These are glycerolipids characterized by an ethanolamine ester of glycerophosphoric acid. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. sn-glycero-3-phosphoethanolamine is a very strong basic compound (based on its pKa). |
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| Structure | |
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| Synonyms | | Value | Source |
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| Glycerophosphorylethanolamine | ChEBI | | sn-Glycerol-3-phosphoethanolamine | ChEBI | | Glycerophosphoethanolamine | MeSH | | Glycerylphosphorylethanolamine | MeSH | | GPEA | HMDB | | Glycerol 3-phosphoethanolamine | HMDB | | Glycerol 3-phosphorylethanolamine | HMDB | | Glycerol phosphorylethanolamine | HMDB | | Glyceryl-3-phosphorylethanolamine | HMDB | | alpha-Glycerophosphorylethanolamine | HMDB | | sn-Glycero-3-phosphoethanolamine | HMDB | | α-Glycerophosphorylethanolamine | HMDB |
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| Chemical Formula | C5H14NO6P |
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| Average Molecular Weight | 215.1415 |
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| Monoisotopic Molecular Weight | 215.055873697 |
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| IUPAC Name | (2-aminoethoxy)(2,3-dihydroxypropoxy)phosphinic acid |
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| Traditional Name | glycerophosphorylethanolamine |
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| CAS Registry Number | 1190-00-7 |
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| SMILES | NCCOP(O)(=O)OCC(O)CO |
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| InChI Identifier | InChI=1S/C5H14NO6P/c6-1-2-11-13(9,10)12-4-5(8)3-7/h5,7-8H,1-4,6H2,(H,9,10) |
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| InChI Key | JZNWSCPGTDBMEW-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as glycerophosphoethanolamines. These are glycerolipids characterized by an ethanolamine ester of glycerophosphoric acid. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Glycerophospholipids |
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| Sub Class | Glycerophosphoethanolamines |
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| Direct Parent | Glycerophosphoethanolamines |
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| Alternative Parents | |
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| Substituents | - Sn-glycero-3-phosphoethanolamine
- Phosphoethanolamine
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Secondary alcohol
- 1,2-diol
- Primary amine
- Primary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Primary aliphatic amine
- Organic nitrogen compound
- Amine
- Organopnictogen compound
- Alcohol
- 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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| Disposition | Source: Biological location: |
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| Process | Naturally occurring process: |
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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 | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - Kish SJ, Robitaille Y, Ball M, Gilbert J, Deck JH, Chang LJ, Schut L: Glycerophosphoethanolamine concentration is elevated in brain of patients with dominantly inherited olivopontocerebellar atrophy. Neurosci Lett. 1990 Dec 11;120(2):209-11. [PubMed:2293106 ]
- Perry TL, Hansen S, Gandham SS: Postmortem changes of amino compounds in human and rat brain. J Neurochem. 1981 Feb;36(2):406-10. [PubMed:7463068 ]
- Nitsch RM, Blusztajn JK, Pittas AG, Slack BE, Growdon JH, Wurtman RJ: Evidence for a membrane defect in Alzheimer disease brain. Proc Natl Acad Sci U S A. 1992 Mar 1;89(5):1671-5. [PubMed:1311847 ]
- Jensen JE, Drost DJ, Menon RS, Williamson PC: In vivo brain (31)P-MRS: measuring the phospholipid resonances at 4 Tesla from small voxels. NMR Biomed. 2002 Aug;15(5):338-47. [PubMed:12203225 ]
- Nelson C, Moffat B, Jacobsen N, Henzel WJ, Stults JT, King KL, McMurtrey A, Vandlen R, Spencer SA: Glycerophosphorylethanolamine (GPEA) identified as an hepatocyte growth stimulator in liver extracts. Exp Cell Res. 1996 Nov 25;229(1):20-6. [PubMed:8940245 ]
- Fallbrook A, Turenne SD, Mamalias N, Kish SJ, Ross BM: Phosphatidylcholine and phosphatidylethanolamine metabolites may regulate brain phospholipid catabolism via inhibition of lysophospholipase activity. Brain Res. 1999 Jul 10;834(1-2):207-10. [PubMed:10407117 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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