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2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) (M2MDB001551)

Record Information
Version2.0
Creation Date2012-07-30 14:54:41 -0600
Update Date2015-06-03 17:20:43 -0600
Secondary Accession Numbers
  • ECMDB21142
Identification
Name:2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0)
Description2-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
MOLSDFPDBSMILESInChI
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
Weight:Average: 453.5503
Monoisotopic: 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
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent2-acyl-sn-glycero-3-phosphoethanolamines
Alternative Parents
Substituents
  • 2-monoacyl-sn-glycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Primary amine
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0026 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity117.41 m³·mol⁻¹ChemAxon
Polarizability52.38 ųChemAxon
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
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + PG(16:0/16:0) > Acyl phosphatidylglycerol (N-C16:0) + Glycerylphosphorylethanolamine
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
1. Lysophospholipase L2
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.
Protein Details
2. Phospholipase A1
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.
Protein Details
3. Bifunctional protein aas
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].
Protein Details
4. Major outer membrane lipoprotein Lpp
General function:
Involved in lipid binding
Specific function:
Interacts with the peptidoglycan both covalently and noncovalently. This interaction contributes to the maintenance of the structural and functional integrity of the cell envelope
Gene Name:
lpp
Uniprot ID:
P69776
Molecular weight:
8323
Protein Details
5. Apolipoprotein N-acyltransferase
General function:
Involved in N-acyltransferase activity
Specific function:
Transfers the fatty acyl group on membrane lipoproteins
Gene Name:
lnt
Uniprot ID:
P23930
Molecular weight:
57065

Transporters

Protein Details
1. Lysophospholipid transporter lplT
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