1.0 2016-10-03 18:19:38 UTC 2020-05-21 16:28:41 UTC BMDB0011503 BMDB11503 LysoPE(16:0/0:0) Lysolysope(16:0/0:0), also known as Lysolysope(16:0/0:0) or lysolysope(16:0/0:0), belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphoethanolamine. Thus, lysolysope(16:0/0:0) is considered to be a glycerophosphoethanolamine lipid molecule. Lysolysope(16:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lysolysope(16:0/0:0) exists in all living species, ranging from bacteria to humans. In cattle, lysolysope(16:0/0:0) is involved in the metabolic pathway called phospholipid biosynthesis pathway. 1-Hexadecanoyl-sn-glycero-3-phosphoethanolamine 1-Palmitoyl-gpe 1-Palmitoyl-gpe (16:0) 1-Palmitoyl-sn-glycero-3-phosphoethanolamine zwitterion 2-Ammonioethyl (2R)-2-hydroxy-3-(palmitoyloxy)propyl phosphate GPE(16:0) GPE(16:0/0:0) PE(16:0/0:0) 2-Ammonioethyl (2R)-2-hydroxy-3-(palmitoyloxy)propyl phosphoric acid 1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine Hexadecanoyl-lysophosphatidylethanolamine LPE(16:0) LPE(16:0/0:0) Lyso-pe(16:0) Lyso-pe(16:0/0:0) LysoPE(16:0) Lysophosphatidylethanolamine(16:0) Lysophosphatidylethanolamine(16:0/0:0) 1-Hexadecanoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine 1-Hexadecanoylglycerophosphoethanolamine 1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphatidylethanolamine 1-Palmitoyl-3-glycerylphosphorylethanolamine 1-Palmitoyl-sn-glycero-3-phosphoethanolamine 1-Palmitoyl-sn-glycerol-3-L-alpha-phosphorylethanolamine 1-Palmitoyl-sn-glycerol-3-L-α-phosphorylethanolamine 1-Palmitoyl-sn-glycerol-3-phosphylethanolamine 1-Palmitoyl-sn-glycerophosphatidylethanolamine 1-Palmitoylglycero-3-phosphorylethanolamine 1-Palmitoylglycerophosphoethanolamine 3-Palmitoyl-DL-glycerol-1-phosphorylethanolamine Palmitoyl lysophosphatidylethanolamine 1-Palmitoyl-lysophosphatidylethanolamine LysoPE(16:0/0:0) C21H44NO7P 453.5503 453.285539279 (2-aminoethoxy)[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphinic acid 2-aminoethoxy(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxyphosphinic acid 53862-35-4 [H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OCCN InChI=1S/C21H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)27-18-20(23)19-29-30(25,26)28-17-16-22/h20,23H,2-19,22H2,1H3,(H,25,26)/t20-/m1/s1 YVYMBNSKXOXSKW-HXUWFJFHSA-N belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphoethanolamine. Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoethanolamines 1-acyl-sn-glycero-3-phosphoethanolamines Amino acids and derivatives Carbonyl compounds Carboxylic acid esters Dialkyl phosphates Fatty acid esters Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Phosphoethanolamines Secondary alcohols 1-monoacyl-sn-glycero-3-phosphoethanolamine Alcohol Aliphatic acyclic compound Alkyl phosphate Amine Amino acid or derivatives Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl phosphate Fatty acid ester Fatty acyl Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphoethanolamine Phosphoric acid ester Primary aliphatic amine Primary amine Secondary alcohol Aliphatic acyclic compounds 1-acyl-sn-glycero-3-phosphoethanolamine Monoacylglycerophosphoethanolamines Solid logp 4.10 ALOGPS logs -5.28 ALOGPS logp 3.53 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic 10 ChemAxon iupac (2-aminoethoxy)[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphinic acid ChemAxon average_mass 453.5503 ChemAxon mono_mass 453.285539279 ChemAxon smiles [H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OCCN ChemAxon formula C21H44NO7P ChemAxon inchi InChI=1S/C21H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)27-18-20(23)19-29-30(25,26)28-17-16-22/h20,23H,2-19,22H2,1H3,(H,25,26)/t20-/m1/s1 ChemAxon inchikey YVYMBNSKXOXSKW-HXUWFJFHSA-N ChemAxon polar_surface_area 128.31 ChemAxon refractivity 117.41 ChemAxon polarizability 52.25 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge 0 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 19244 Specdb::CMs 39628 Specdb::CMs 156537 Specdb::MsMs 308758 Specdb::MsMs 308759 Specdb::MsMs 308760 Specdb::MsMs 353026 Specdb::MsMs 353027 Specdb::MsMs 353028 Specdb::MsMs 2253014 Specdb::MsMs 2253481 Specdb::MsMs 2255464 Specdb::MsMs 2348036 Specdb::MsMs 2348037 Specdb::MsMs 2348038 Specdb::MsMs 2587597 Specdb::MsMs 2587598 Specdb::MsMs 2587599 Specdb::NmrOneD 261088 Specdb::NmrOneD 261089 Specdb::NmrOneD 261090 Specdb::NmrOneD 261091 Specdb::NmrOneD 261092 Specdb::NmrOneD 261093 Specdb::NmrOneD 261094 Specdb::NmrOneD 261095 Specdb::NmrOneD 261096 Specdb::NmrOneD 261097 Specdb::NmrOneD 261098 Specdb::NmrOneD 261099 Specdb::NmrOneD 261100 Specdb::NmrOneD 261101 Specdb::NmrOneD 261102 Specdb::NmrOneD 261103 Specdb::NmrOneD 261104 Specdb::NmrOneD 261105 Specdb::NmrOneD 261106 Specdb::NmrOneD 261107 All Tissues 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 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 7826019 FDB028219 9547069 73004 BMDBP00783 Cytosolic phospholipase A2 A4IFJ5 PLA2G4A Enzyme