2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) (PAMDB001554)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001554
Identification
Name: 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1)
Description:2-acyl-sn-glycero-3-phosphoethanolamine (n-c18:1) 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: C23H43NO7P
Average Molecular Weight: 476.5638
Monoisotopic Molecular Weight: 476.277714247
InChI Key: QLFHRWIZXUHUNT-BQYQJAHWSA-M
InChI:InChI=1S/C23H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)31-22(20-25)21-30-32(27,28)29-19-18-24/h7-8,22,25H,2-6,9-21H2,1H3,(H,27,28)/q+1/p-1/b8-7+
CAS number: Not Available
IUPAC Name:{2-[(3-hydroxy-2-{[(11E)-1-(??-oxidanyliumylidene)octadec-11-en-1-yl]oxy}propyl phosphonato)oxy]ethyl}azanylidene
Traditional IUPAC Name: {2-[(3-hydroxy-2-{[(11E)-1-(??-oxidanyliumylidene)octadec-11-en-1-yl]oxy}propyl phosphonato)oxy]ethyl}azanylidene
SMILES:[H]\C(CCCCCC)=C(\[H])CCCCCCCCCC(=[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 Solubility0.00427 mg/mLALOGPS
logP5.43ALOGPS
logP4.18ChemAxon
logS-5.1ALOGPS
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 Count24ChemAxon
Refractivity125.09 m3·mol-1ChemAxon
Polarizability54.78 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-C18:1) + Adenosine triphosphate + Octadecenoate (N-C18:1) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Hydrogen ion + Octadecenoate (N-C18:1)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecenoate (N-C18:1)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + PG(18:1(11Z)/18:1(11Z)) > Acyl phosphatidylglycerol (N-C18:1) + Glycerylphosphorylethanolamine
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9100200000-2e49a82cddc883839647View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9010000000-ffd5d62a54ff20361764View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-72dc2ee436ea3b2c2df8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2330900000-a3d48d7caa7f5fb9c4c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002o-2910300000-73f01b0ad7102ea84a03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-9480000000-091f345f216d28135d24View 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 IDCPD0-2174
EcoCyc IDCPD0-2174

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