2.0 2012-05-31 09:57:35 -0600 2015-06-03 15:53:12 -0600 ECMDB00114 M2MDB000042 Glycerylphosphorylethanolamine Glycerylphosphorylethanolamine is membrane breakdown product resulting from the cleavage of the lipid group from glycerophosphoethanlomine fatty acids (i.e. phosphatidylethanolamine). Phosphatidylethanolamine is one of the major lipid constituents of E. coli. 2-Aminoethyl ester 1-glycerophosphate 2-Aminoethyl ester 1-Glycerophosphorate 2-Aminoethyl ester 1-Glycerophosphoric acid A-Glycerophosphorylethanolamine Alpha-Glycerophosphorylethanolamine Glycerol 3-phosphoethanolamine Glycerol 3-phosphorylethanolamine Glycerophosphoethanolamine Glycerophosphorylethanolamine Glyceryl-3-phosphorylethanolamine Glycerylphosphorylethanolamine GPEA α-Glycerophosphorylethanolamine C5H14NO6P 215.1415 215.055873697 [(2,3-dihydroxypropyl)(2-hydroxyethyl)amino]phosphonic acid GPEA 1190-00-7 OCCN(CC(O)CO)P(O)(O)=O InChI=1S/C5H14NO6P/c7-2-1-6(13(10,11)12)3-5(9)4-8/h5,7-9H,1-4H2,(H2,10,11,12) FRMZOWIQVCBEAC-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -1.90 ALOGPS logs -0.87 ALOGPS solubility 2.92e+01 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 2.8 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac [(2,3-dihydroxypropyl)(2-hydroxyethyl)amino]phosphonic acid ChemAxon average_mass 215.1415 ChemAxon mono_mass 215.055873697 ChemAxon smiles OCCN(CC(O)CO)P(O)(O)=O ChemAxon formula C5H14NO6P ChemAxon inchi InChI=1S/C5H14NO6P/c7-2-1-6(13(10,11)12)3-5(9)4-8/h5,7-9H,1-4H2,(H2,10,11,12) ChemAxon inchikey FRMZOWIQVCBEAC-UHFFFAOYSA-N ChemAxon polar_surface_area 121.46 ChemAxon refractivity 44.53 ChemAxon polarizability 18.51 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 Specdb::CMs 25657 Specdb::CMs 37299 Specdb::NmrOneD 290955 Specdb::NmrOneD 290956 Specdb::NmrOneD 290957 Specdb::NmrOneD 290958 Specdb::NmrOneD 290959 Specdb::NmrOneD 290960 Specdb::NmrOneD 290961 Specdb::NmrOneD 290962 Specdb::NmrOneD 290963 Specdb::NmrOneD 290964 Specdb::NmrOneD 290965 Specdb::NmrOneD 290966 Specdb::NmrOneD 290967 Specdb::NmrOneD 290968 Specdb::NmrOneD 290969 Specdb::NmrOneD 290970 Specdb::NmrOneD 290971 Specdb::NmrOneD 290972 Specdb::NmrOneD 290973 Specdb::NmrOneD 290974 Specdb::MsMs 26459 Specdb::MsMs 26460 Specdb::MsMs 26461 Specdb::MsMs 33017 Specdb::MsMs 33018 Specdb::MsMs 33019 HMDB00114 123874 17215919 C01233 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 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. 19212411 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. 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. 12203225 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. 10407117 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. 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. 7463068 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. 8940245 Tronconi, Giovanni. Process for the chromatographic isolation of 1-(a)-glycerylphosphorylcholine and of L-(a)-glycerylphosphorylethanolamine. PCT Int. Appl. (1990), 18 pp. Lysophospholipase L2 P07000 PLDB_ECOLI pldB http://ecmdb.ca/proteins/P07000.xml Glycerophosphoryl diester phosphodiesterase P09394 GLPQ_ECOLI glpQ http://ecmdb.ca/proteins/P09394.xml Acyl-CoA thioesterase I P0ADA1 TESA_ECOLI tesA http://ecmdb.ca/proteins/P0ADA1.xml sn-glycerol-3-phosphate import ATP-binding protein UgpC P10907 UGPC_ECOLI ugpC http://ecmdb.ca/proteins/P10907.xml Glycerophosphoryl diester phosphodiesterase_ P10908 UGPQ_ECOLI ugpQ http://ecmdb.ca/proteins/P10908.xml sn-glycerol-3-phosphate transport system permease protein ugpA P10905 UGPA_ECOLI ugpA http://ecmdb.ca/proteins/P10905.xml sn-glycerol-3-phosphate transport system permease protein ugpE P10906 UGPE_ECOLI ugpE http://ecmdb.ca/proteins/P10906.xml sn-glycerol-3-phosphate-binding periplasmic protein ugpB P0AG80 UGPB_ECOLI ugpB http://ecmdb.ca/proteins/P0AG80.xml sn-glycerol-3-phosphate import ATP-binding protein UgpC P10907 UGPC_ECOLI ugpC http://ecmdb.ca/proteins/P10907.xml sn-glycerol-3-phosphate transport system permease protein ugpA P10905 UGPA_ECOLI ugpA http://ecmdb.ca/proteins/P10905.xml sn-glycerol-3-phosphate transport system permease protein ugpE P10906 UGPE_ECOLI ugpE http://ecmdb.ca/proteins/P10906.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml sn-glycerol-3-phosphate-binding periplasmic protein ugpB P0AG80 UGPB_ECOLI ugpB http://ecmdb.ca/proteins/P0AG80.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + Glycerylphosphorylethanolamine > ADP + Glycerylphosphorylethanolamine + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Glycerylphosphorylethanolamine > ADP + Glycerylphosphorylethanolamine + Hydrogen ion + Phosphate 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerylphosphorylethanolamine + Hydrogen ion 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + tetradecanoate (n-C14:0) 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Tetradecenoate (N-C14:1) 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Palmitic acid 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Hexadecenoate (n-C16:1) 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecanoate (N-C18:0) 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecenoate (N-C18:1) Glycerylphosphorylethanolamine + Water > Ethanolamine + Glycerol 3-phosphate + Hydrogen ion 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerylphosphorylethanolamine + Hydrogen ion 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + PG(12:0/12:0) > Acyl phosphatidylglycerol (N-C12:0) + Glycerylphosphorylethanolamine 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + tetradecanoate (n-C14:0) 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + PG(14:0/14:0) > Acyl phosphatidylglycerol (N-C14:0) + Glycerylphosphorylethanolamine 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Tetradecenoate (N-C14:1) 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + PG(14:1(7Z)/14:1(7Z)) > Acyl phosphatidylglycerol (N-C14:1) + Glycerylphosphorylethanolamine 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Palmitic acid 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + PG(16:0/16:0) > Acyl phosphatidylglycerol (N-C16:0) + Glycerylphosphorylethanolamine 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Hexadecenoate (n-C16:1) 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1) + PG(16:1(9Z)/16:1(9Z)) > Acyl phosphatidylglycerol (N-C16:1) + Glycerylphosphorylethanolamine 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecanoate (N-C18:0) 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + PG(18:0/18:0) > Acyl phosphatidylglycerol (N-C18:0) + Glycerylphosphorylethanolamine 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecenoate (N-C18:1) 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + PG(18:1(11Z)/18:1(11Z)) > Acyl phosphatidylglycerol (N-C18:1) + Glycerylphosphorylethanolamine Glycerylphosphorylethanolamine + Water <> Ethanolamine + Glycerol 3-phosphate R01470