Record Information
Version2.0
Creation Date2012-07-30 14:54:41 -0600
Update Date2015-06-03 17:20:44 -0600
Secondary Accession Numbers
  • ECMDB21143
Identification
Name:2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1)
Description2-acyl-sn-glycero-3-phosphoethanolamine (n-c16:1) belongs to the class of Lysophosphatidylethanolamines. These are glycerophosphoetahnolamines (molecules containing an ethanolamine moiety attached to the phosphate group linked to a glycerol) with one saturated fatty acid bonded to the glycerol moiety through an ester linkage. (inferred from compound structure)
Structure
Thumb
Synonyms:Not Available
Chemical Formula:C21H39NO7P
Weight:Average: 448.5106
Monoisotopic: 448.246414119
InChI Key:XUIKIGYKPTVAIJ-BQYQJAHWSA-M
InChI:InChI=1S/C21H40NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)29-20(18-23)19-28-30(25,26)27-17-16-22/h7-8,20,23H,2-6,9-19H2,1H3,(H,25,26)/q+1/p-1/b8-7+
CAS number:Not Available
IUPAC Name:{2-[(3-hydroxy-2-{[(9E)-1-(λ³-oxidanyliumylidene)hexadec-9-en-1-yl]oxy}propyl phosphonato)oxy]ethyl}azanylidene
Traditional IUPAC Name:{2-[(3-hydroxy-2-{[(9E)-1-(λ³-oxidanyliumylidene)hexadec-9-en-1-yl]oxy}propyl phosphonato)oxy]ethyl}azanylidene
SMILES:[H]\C(CCCCCC)=C(\[H])CCCCCCCC(=[O+])OC(CO)COP([O-])(=O)OCC[N]
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP4.72ALOGPS
logP3.29ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity115.89 m³·mol⁻¹ChemAxon
Polarizability50.54 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9100200000-12f8656a208e1ae71cccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9010000000-ee519f3e6d2cc0b628d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-218f8a9fa3a526e73caeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2330900000-cf8be65b05e6fec8af8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000g-2910300000-781de3278f3e9922f91dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kd0-9480000000-17292ab23f18fe10b5d1View in MoNA
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
  • 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 IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2204
EcoCyc IDCPD0-2204

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Uniprot ID:
P07000
Molecular weight:
38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in phospholipase activity
Specific function:
Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
Gene Name:
pldA
Uniprot ID:
P0A921
Molecular weight:
33163
Reactions
Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate.
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate.
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
Gene Name:
aas
Uniprot ID:
P31119
Molecular weight:
80699
Reactions
Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine.
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein].

Transporters

General function:
Involved in lipid transporter activity
Specific function:
Catalyzes the facilitated diffusion of 2-acyl-glycero-3- phosphoethanolamine (2-acyl-GPE) into the cell
Gene Name:
lplT
Uniprot ID:
P39196
Molecular weight:
41655