Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000551
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
Thumb
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
Average Molecular Weight: 286.2393
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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 ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent 2-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 2-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Dialkyl phosphate
  • Choline
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • 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:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.91 mg/mLALOGPS
logP-2.3ALOGPS
logP-5.3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity74.47 m3·mol-1ChemAxon
Polarizability26.93 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
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
External Links:
ResourceLink
CHEBI ID11502
HMDB IDNot Available
Pubchem Compound ID24798686
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc ID2-Acylglycero-Phosphocholines
EcoCyc ID2-Acylglycero-Phosphocholines