2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1) (PAMDB001552)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001552
Identification
Name: 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1)
Description:2-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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:Not Available
Chemical Formula: C21H39NO7P
Average Molecular Weight: 448.5106
Monoisotopic Molecular Weight: 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-(??-oxidanyliumylidene)hexadec-9-en-1-yl]oxy}propyl phosphonato)oxy]ethyl}azanylidene
Traditional IUPAC Name: {2-[(3-hydroxy-2-{[(9E)-1-(??-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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glycerophospholipids. These are derivatives of glycerophosphoric acid that contains at least one O-acyl, or O-alkyl, or O-(1-alkenyl) group attached to the glycerol residue.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassNot Available
Direct Parent Glycerophospholipids
Alternative Parents
Substituents
  • Glycerophospholipid
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic nitrene
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic zwitterion
  • Organic salt
  • 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 Solubility0.0163 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity115.89 m3·mol-1ChemAxon
Polarizability50.54 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1) + PG(16:1(9Z)/16:1(9Z)) > Acyl phosphatidylglycerol (N-C16:1) + Glycerylphosphorylethanolamine
Pathways:
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

Protein Details
• Lysophospholipase L2
General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Locus Tag:
PA5089
Molecular weight:
83.4 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.

Transporters