2.0 2012-05-31 14:01:47 -0600 2015-06-03 15:54:36 -0600 ECMDB04005 M2MDB000551 2-Acylglycerophosphocholine 2-acylglycerophosphocholine belongs to the class of Lysophosphatidylcholines. These are glycerophosphocholines (molecules containing a choline moiety attached to the phosphate group linked to a glycerol) in which the glycerol is attached to one saturated fatty acid each through an ester linkage. (inferred from compound structure)2-acyl-sn-glycero-3-phosphocholines are a class of phospholipids that are intermediates in the metabolism of lipids. Because they result from the hydrolysis of an acyl group from the sn-1 position of phosphatidylcholine, they are also called 1-lysophosphatidylcholine (or 1-lysoPC, in short). The synthesis of phosphatidylcholines with specific fatty acids occurs through the synthesis of 1-lysoPC. The formation of various other lipids generates 1-lysoPC as a by-product. Other synonyms for this class of compounds are 2-acylglycero-3-phosphocholine, 1-lyso-2-acyl-sn-glycero-3-phosphocholine, β-lysophosphatidylcholine, 2-acylglycerophosphocholine, L-1-lysolecithin and 1-lecithin. (WikiPedia) 2-Acylglycerophosphocholines A β-lysophosphatidylcholine A 1-lyso-2-acyl-<i>sn</i>-glycero-3-phosphocholine a 1-lyso-2-Acyl-sn-glycero-3-phosphocholine A 1-lysolecithin A 2-acyl-<i>sn</i>-glycero-3-phosphocholine A 2-acyl-sn-glycero-3-phosphocholine A 2-acylglycero-3-phosphocholine A 2-acylglycerophosphocholine A L-1-lysolecithin C9H21NO7P 286.2393 286.105563543 [2-(formyloxy)-3-hydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid 2-(formyloxy)-3-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid C[N+](C)(C)CCOP(O)(=O)OCC(CO)OC=O InChI=1S/C9H20NO7P/c1-10(2,3)4-5-16-18(13,14)17-7-9(6-11)15-8-12/h8-9,11H,4-7H2,1-3H3/p+1 WOBXACRJIURDTO-UHFFFAOYSA-O Cytoplasm Periplasm logp -2.28 ALOGPS logs -2.23 ALOGPS solubility 1.91e+00 g/l ALOGPS logp -5.3 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -3 ChemAxon iupac [2-(formyloxy)-3-hydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid ChemAxon average_mass 286.2393 ChemAxon mono_mass 286.105563543 ChemAxon smiles C[N+](C)(C)CCOP(O)(=O)OCC(CO)OC=O ChemAxon formula C9H21NO7P ChemAxon inchi InChI=1S/C9H20NO7P/c1-10(2,3)4-5-16-18(13,14)17-7-9(6-11)15-8-12/h8-9,11H,4-7H2,1-3H3/p+1 ChemAxon inchikey WOBXACRJIURDTO-UHFFFAOYSA-O ChemAxon polar_surface_area 102.29 ChemAxon refractivity 74.47 ChemAxon polarizability 26.93 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 1 ChemAxon Glycerophospholipid metabolism ec00564 alpha-Linolenic acid metabolism ec00592 Metabolic pathways eco01100 phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::NmrOneD 282749 Specdb::NmrOneD 282750 Specdb::NmrOneD 282751 Specdb::NmrOneD 282752 Specdb::NmrOneD 282753 Specdb::NmrOneD 282754 Specdb::NmrOneD 282755 Specdb::NmrOneD 282756 Specdb::NmrOneD 282757 Specdb::NmrOneD 282758 Specdb::NmrOneD 282759 Specdb::NmrOneD 282760 Specdb::NmrOneD 282761 Specdb::NmrOneD 282762 Specdb::NmrOneD 282763 Specdb::NmrOneD 282764 Specdb::NmrOneD 282765 Specdb::NmrOneD 282766 Specdb::NmrOneD 282767 Specdb::NmrOneD 282768 24798686 11502 2-Acylglycero-Phosphocholines Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 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 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. 22102590 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Lysophospholipase L2 P07000 PLDB_ECOLI pldB http://ecmdb.ca/proteins/P07000.xml Phospholipase A1 P0A921 PA1_ECOLI pldA http://ecmdb.ca/proteins/P0A921.xml 2-Acylglycerophosphocholine + Water a carboxylate + Glycerophosphocholine + Hydrogen ion LYSOPHOSPHOLIPASE-RXN Phosphatidylcholine + Water > 2-Acylglycerophosphocholine + a carboxylate Phosphatidylcholine + Water <> Carboxylate + 2-Acylglycerophosphocholine R01314