2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) (PAMDB001553)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001553
Identification
Name: 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0)
Description:2-acyl-sn-glycero-3-phosphoethanolamine (n-c18:0) 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:
  • 1-2-aminoethoxy(hydroxy)phosphoryloxy-3-hydroxypropan-2-yl octadecanoate
  • 1-2-Aminoethoxy(hydroxy)phosphoryloxy-3-hydroxypropan-2-yl octadecanoic acid
Chemical Formula: C23H48NO7P
Average Molecular Weight: 481.6035
Monoisotopic Molecular Weight: 481.316839407
InChI Key: KIHAGWUUUHJRMS-UHFFFAOYSA-N
InChI:InChI=1S/C23H48NO7P/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/h22,25H,2-21,24H2,1H3,(H,27,28)
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[3-hydroxy-2-(octadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy(3-hydroxy-2-(octadecanoyloxy)propoxy)phosphinic acid
SMILES:CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(O)(=O)OCCN
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-2 position, and linked at position 3 to a phosphoethanolamine.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent 2-acyl-sn-glycero-3-phosphoethanolamines
Alternative Parents
Substituents
  • 2-monoacyl-sn-glycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • 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 Solubility0.00145 mg/mLALOGPS
logP4.74ALOGPS
logP4.42ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 Å2ChemAxon
Rotatable Bond Count25ChemAxon
Refractivity126.61 m3·mol-1ChemAxon
Polarizability56.67 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-C18:0) + Adenosine triphosphate + Octadecanoate (N-C18:0) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Hydrogen ion + Octadecanoate (N-C18:0)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecanoate (N-C18:0)
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9130200000-9cbc60f7746d76e7e0b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120000000-c907d5e8f44312d95b4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9030000000-bdb75c3be8f87af19b10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2670900000-27dafc5b8a82ab8ab032View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9630200000-79fb805049708e17184fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9210000000-47e4131ac3881973a00dView in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID46173362
Kegg IDNot Available
ChemSpider ID24608314
Wikipedia IDNot Available
BioCyc IDCPD0-2223
EcoCyc IDCPD0-2223

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