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Record Information
Version	2.0
Creation Date	2012-05-31 14:01:47 -0600
Update Date	2015-06-03 15:54:36 -0600
Secondary Accession Numbers	ECMDB04005
Identification
Name:	2-Acylglycerophosphocholine
Description	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)
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xb1b97628> Close
Synonyms:	2-Acylglycerophosphocholines A β-lysophosphatidylcholine A 1-lyso-2-acyl-sn-glycero-3-phosphocholine a 1-lyso-2-Acyl-sn-glycero-3-phosphocholine A 1-lysolecithin A 2-acyl-sn-glycero-3-phosphocholine A 2-acyl-sn-glycero-3-phosphocholine A 2-acylglycero-3-phosphocholine A 2-acylglycerophosphocholine A L-1-lysolecithin
Chemical Formula:	C9H21NO7P
Weight:	Average: 286.2393 Monoisotopic: 286.105563543
InChI Key:	WOBXACRJIURDTO-UHFFFAOYSA-O
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
CAS number:	Not Available
IUPAC Name:	[2-(formyloxy)-3-hydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid
Traditional IUPAC Name:	2-(formyloxy)-3-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid
SMILES:	C[N+](C)(C)CCOP(O)(=O)OCC(CO)OC=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-2 position, and linked at position 3 to a phosphocholine.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Glycerophospholipids
Sub Class	Glycerophosphocholines
Direct Parent	2-acyl-sn-glycero-3-phosphocholines
Alternative Parents	Phosphocholines Dialkyl phosphates Tetraalkylammonium salts Carboxylic acid esters Monocarboxylic acids and derivatives Primary alcohols Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds Amines Organic cations
Substituents	2-acyl-sn-glycero-3-phosphocholine Phosphocholine Dialkyl phosphate Organic phosphoric acid derivative Phosphoric acid ester Alkyl phosphate Tetraalkylammonium salt Quaternary ammonium salt Carboxylic acid ester Monocarboxylic acid or derivatives Carboxylic acid derivative Organic salt Hydrocarbon derivative Primary alcohol Organic oxide Organopnictogen compound Organooxygen compound Organonitrogen compound Organic oxygen compound Organic nitrogen compound Carbonyl group Amine Alcohol Organic cation Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 1.91 g/L ALOGPS logP -2.3 ALOGPS logP -5.3 ChemAxon logS -2.2 ALOGPS pKa (Strongest Acidic) 1.86 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 102.29 Ų ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 74.47 m³·mol⁻¹ ChemAxon Polarizability 26.93 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2-Acylglycerophosphocholine + Water a carboxylate + Glycerophosphocholine + Hydrogen ion Phosphatidylcholine + Water > 2-Acylglycerophosphocholine + a carboxylate Phosphatidylcholine + Water <> Carboxylate + 2-Acylglycerophosphocholine
SMPDB Pathways:	Not Available
KEGG Pathways:	Glycerophospholipid metabolism ec00564 Metabolic pathways eco01100 alpha-Linolenic acid metabolism ec00592
EcoCyc Pathways:	phospholipid biosynthesis I PHOSLIPSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 22080510 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. Pubmed: 21097882 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 11502 HMDB ID Not Available Pubchem Compound ID 24798686 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID 2-Acylglycero-Phosphocholines EcoCyc ID 2-Acylglycero-Phosphocholines

Enzymes