1.0 2016-09-30 22:19:43 UTC 2020-05-11 20:46:28 UTC BMDB0000114 BMDB00114 Glycerylphosphorylethanolamine Glycerylphosphorylethanolamine, also known as glycerylphosphorylethanolamine, belongs to the class of organic compounds known as organic phosphoramides. These are organic compounds containing the phosphoric acid amide functional group. Glycerylphosphorylethanolamine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Glycerylphosphorylethanolamine exists in all living organisms, ranging from bacteria to humans. Glycerylphosphorylethanolamine can be converted into glycerol 3-phosphate and ethanolamine through the action of the enzyme glycerophosphodiester phosphodiesterase 1. In cattle, glycerylphosphorylethanolamine is involved in the metabolic pathway called phospholipid biosynthesis pathway. 2-Aminoethyl ester 1-glycerophosphoric acid a-Glycerophosphorylethanolamine alpha-Glycerophosphorylethanolamine Glycerol 3-phosphoethanolamine Glycerol 3-phosphorylethanolamine Glycerophosphoethanolamine Glycerophosphorylethanolamine Glyceryl-3-phosphorylethanolamine GPEA C5H14NO6P 215.1415 215.055873697 [(2,3-dihydroxypropyl)(2-hydroxyethyl)amino]phosphonic acid GPEA 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 belongs to the class of organic compounds known as organic phosphoramides. These are organic compounds containing the phosphoric acid amide functional group. Organic compounds Organic acids and derivatives Organic phosphoric acids and derivatives Organic phosphoramides Organic phosphoramides Alkanolamines Hydrocarbon derivatives Organic oxides Organopnictogen compounds Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Alkanolamine Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid amide Organonitrogen compound Organooxygen compound Organopnictogen compound Primary alcohol Secondary alcohol Aliphatic acyclic compounds Solid logp -1.90 ALOGPS logs -0.87 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 number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Phospholipid Biosynthesis SMP0087228 Specdb::CMs 25657 Specdb::CMs 37299 Specdb::MsMs 26459 Specdb::MsMs 26460 Specdb::MsMs 26461 Specdb::MsMs 33017 Specdb::MsMs 33018 Specdb::MsMs 33019 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 Brain Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 FDB021895 22833510 134287 Tronconi, Giovanni. Process for the chromatographic isolation of 1-(a)-glycerylphosphorylcholine and of L-(a)-glycerylphosphorylethanolamine. PCT Int. Appl. (1990), 18 pp.