2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) (PAMDB001551)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001551
Identification
Name: 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0)
Description:2-acyl-sn-glycero-3-phosphoethanolamine (n-c16:0) 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 hexadecanoate
  • 1-2-Aminoethoxy(hydroxy)phosphoryloxy-3-hydroxypropan-2-yl hexadecanoic acid
Chemical Formula: C21H44NO7P
Average Molecular Weight: 453.5503
Monoisotopic Molecular Weight: 453.285539279
InChI Key: CKPBBEOJHAPPBT-UHFFFAOYSA-N
InChI:InChI=1S/C21H44NO7P/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/h20,23H,2-19,22H2,1H3,(H,25,26)
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[2-(hexadecanoyloxy)-3-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy(2-(hexadecanoyloxy)-3-hydroxypropoxy)phosphinic acid
SMILES:CCCCCCCCCCCCCCCC(=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 Solubility0.00255 mg/mLALOGPS
logP4.06ALOGPS
logP3.53ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 Å2ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity117.41 m3·mol-1ChemAxon
Polarizability52.38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
applipoprotein + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + lipoprotein
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Adenosine triphosphate + Palmitic acid > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Hydrogen ion + Palmitic acid
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Palmitic acid
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9220200000-37a5e73ad6b88ef1efa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9220000000-71392c5a02c4f8c20a0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-bfdd440aa5671444765bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-2781900000-ad75ca20a5ec4d332d01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9630200000-402c225050e06ef55f13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9210000000-a0a6f1b40fecbd260367View 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 ID46173130
Kegg IDNot Available
ChemSpider ID24608312
Wikipedia IDNot Available
BioCyc IDCPD0-2177
EcoCyc IDCPD0-2177

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.
Protein Details
• Apolipoprotein N-acyltransferase
General function:
Involved in N-acyltransferase activity
Specific function:
Transfers the fatty acyl group on membrane lipoproteins
Gene Name:
lnt
Locus Tag:
PA3984
Molecular weight:
56 kDa

Transporters