1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) (ECMDB21114) (M2MDB001523)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2012-07-30 14:54:39 -0600
Update Date2015-06-03 17:20:40 -0600
Secondary Accession Numbers
  • ECMDB21114
Identification
Name:1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0)
Description1-acyl-sn-glycero-3-phosphoethanolamine (n-c14:0) 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:
  • 3-2-aminoethoxy(hydroxy)phosphoryloxy-2-hydroxypropyl tetradecanoate
  • 3-2-Aminoethoxy(hydroxy)phosphoryloxy-2-hydroxypropyl tetradecanoic acid
Chemical Formula:C19H40NO7P
Weight:Average: 425.4972
Monoisotopic: 425.254239151
InChI Key:RPXHXZNGZBHSMJ-UHFFFAOYSA-N
InChI:InChI=1S/C19H40NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(22)25-16-18(21)17-27-28(23,24)26-15-14-20/h18,21H,2-17,20H2,1H3,(H,23,24)
CAS number:Not Available
IUPAC Name:(2-aminoethoxy)[2-hydroxy-3-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name:2-aminoethoxy(2-hydroxy-3-(tetradecanoyloxy)propoxy)phosphinic acid
SMILES:CCCCCCCCCCCCCC(=O)OCC(O)COP(O)(=O)OCCN
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphoethanolamine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent1-acyl-sn-glycero-3-phosphoethanolamines
Alternative Parents
Substituents
  • 1-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
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Primary amine
  • 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 Solubility0.0071 g/LALOGPS
logP3.25ALOGPS
logP2.64ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity108.21 m³·mol⁻¹ChemAxon
Polarizability48.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + tetradecanoate (n-C14:0)
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + Hydrogen ion + tetradecanoate (n-C14:0)
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_3_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9230200000-ca63d24a372804c1c921View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9220000000-ba5df782e27f396606bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-76b860a651a1281fb5cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05di-1292300000-db37d56873d3dfb6dc17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-6690000000-a4effec34a4f6fb1616dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9110000000-2f7241823bdf1f731c76View 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 ID46173403
Kegg IDNot Available
ChemSpider ID21435856
Wikipedia IDNot Available
BioCyc IDCPD0-2147
EcoCyc IDCPD0-2147

Enzymes

Protein Details
1. 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
2. Acyl-CoA thioesterase I
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Uniprot ID:
P0ADA1
Molecular weight:
23622
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.