2.02012-05-31 09:57:35 -06002015-06-03 15:53:12 -0600ECMDB00114M2MDB000042GlycerylphosphorylethanolamineGlycerylphosphorylethanolamine 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-glycerophosphate2-Aminoethyl ester 1-Glycerophosphorate2-Aminoethyl ester 1-Glycerophosphoric acidA-GlycerophosphorylethanolamineAlpha-GlycerophosphorylethanolamineGlycerol 3-phosphoethanolamineGlycerol 3-phosphorylethanolamineGlycerophosphoethanolamineGlycerophosphorylethanolamineGlyceryl-3-phosphorylethanolamineGlycerylphosphorylethanolamineGPEAα-GlycerophosphorylethanolamineC5H14NO6P215.1415215.055873697[(2,3-dihydroxypropyl)(2-hydroxyethyl)amino]phosphonic acidGPEA1190-00-7OCCN(CC(O)CO)P(O)(O)=OInChI=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-NSolidCytosolExtra-organismPeriplasmlogp-1.90logs-0.87solubility2.92e+01 g/llogp-3.2pka_strongest_acidic2.8pka_strongest_basic-2.6iupac[(2,3-dihydroxypropyl)(2-hydroxyethyl)amino]phosphonic acidaverage_mass215.1415mono_mass215.055873697smilesOCCN(CC(O)CO)P(O)(O)=OformulaC5H14NO6PinchiInChI=1S/C5H14NO6P/c7-2-1-6(13(10,11)12)3-5(9)4-8/h5,7-9H,1-4H2,(H2,10,11,12)inchikeyFRMZOWIQVCBEAC-UHFFFAOYSA-Npolar_surface_area121.46refractivity44.53polarizability18.51rotatable_bond_count6acceptor_count6donor_count5physiological_charge-2formal_charge0Glycerophospholipid metabolismec00564Specdb::CMs25657Specdb::CMs37299Specdb::NmrOneD290955Specdb::NmrOneD290956Specdb::NmrOneD290957Specdb::NmrOneD290958Specdb::NmrOneD290959Specdb::NmrOneD290960Specdb::NmrOneD290961Specdb::NmrOneD290962Specdb::NmrOneD290963Specdb::NmrOneD290964Specdb::NmrOneD290965Specdb::NmrOneD290966Specdb::NmrOneD290967Specdb::NmrOneD290968Specdb::NmrOneD290969Specdb::NmrOneD290970Specdb::NmrOneD290971Specdb::NmrOneD290972Specdb::NmrOneD290973Specdb::NmrOneD290974Specdb::MsMs26459Specdb::MsMs26460Specdb::MsMs26461Specdb::MsMs33017Specdb::MsMs33018Specdb::MsMs33019HMDB0011412387417215919C01233Kanehisa, 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-D114.22080510Sreekumar 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):910-4.19212411Nitsch 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):1671-5.1311847Jensen 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):338-47.12203225Fallbrook 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):207-10.10407117Kish 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):209-11.2293106Perry TL, Hansen S, Gandham SS: Postmortem changes of amino compounds in human and rat brain. J Neurochem. 1981 Feb;36(2):406-10.7463068Nelson 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):20-6.8940245Tronconi, Giovanni. Process for the chromatographic isolation of 1-(a)-glycerylphosphorylcholine and of L-(a)-glycerylphosphorylethanolamine. PCT Int. Appl. (1990), 18 pp. Lysophospholipase L2P07000PLDB_ECOLIpldBhttp://ecmdb.ca/proteins/P07000.xmlGlycerophosphoryl diester phosphodiesteraseP09394GLPQ_ECOLIglpQhttp://ecmdb.ca/proteins/P09394.xmlAcyl-CoA thioesterase IP0ADA1TESA_ECOLItesAhttp://ecmdb.ca/proteins/P0ADA1.xmlsn-glycerol-3-phosphate import ATP-binding protein UgpCP10907UGPC_ECOLIugpChttp://ecmdb.ca/proteins/P10907.xmlGlycerophosphoryl diester phosphodiesterase_P10908UGPQ_ECOLIugpQhttp://ecmdb.ca/proteins/P10908.xmlsn-glycerol-3-phosphate transport system permease protein ugpAP10905UGPA_ECOLIugpAhttp://ecmdb.ca/proteins/P10905.xmlsn-glycerol-3-phosphate transport system permease protein ugpEP10906UGPE_ECOLIugpEhttp://ecmdb.ca/proteins/P10906.xmlsn-glycerol-3-phosphate-binding periplasmic protein ugpBP0AG80UGPB_ECOLIugpBhttp://ecmdb.ca/proteins/P0AG80.xmlsn-glycerol-3-phosphate import ATP-binding protein UgpCP10907UGPC_ECOLIugpChttp://ecmdb.ca/proteins/P10907.xmlsn-glycerol-3-phosphate transport system permease protein ugpAP10905UGPA_ECOLIugpAhttp://ecmdb.ca/proteins/P10905.xmlsn-glycerol-3-phosphate transport system permease protein ugpEP10906UGPE_ECOLIugpEhttp://ecmdb.ca/proteins/P10906.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlsn-glycerol-3-phosphate-binding periplasmic protein ugpBP0AG80UGPB_ECOLIugpBhttp://ecmdb.ca/proteins/P0AG80.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlAdenosine triphosphate + Water + Glycerylphosphorylethanolamine > ADP + Glycerylphosphorylethanolamine + Hydrogen ion + PhosphateAdenosine triphosphate + Water + Glycerylphosphorylethanolamine > ADP + Glycerylphosphorylethanolamine + Hydrogen ion + Phosphate1-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerylphosphorylethanolamine + Hydrogen ion1-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 acid1-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 ion2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerylphosphorylethanolamine + Hydrogen ion2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + PG(12:0/12:0) > Acyl phosphatidylglycerol (N-C12:0) + Glycerylphosphorylethanolamine2-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) + Glycerylphosphorylethanolamine2-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) + Glycerylphosphorylethanolamine2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Palmitic acid2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + PG(16:0/16:0) > Acyl phosphatidylglycerol (N-C16:0) + Glycerylphosphorylethanolamine2-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) + Glycerylphosphorylethanolamine2-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) + Glycerylphosphorylethanolamine2-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) + GlycerylphosphorylethanolamineGlycerylphosphorylethanolamine + Water <> Ethanolamine + Glycerol 3-phosphateR01470