Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000751
Identification
Name: PE(14:0/14:0)
Description:PE(14:0/14:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PE(14:0/14:0), in particular, consists of two tetradecanoyl chains at positions C-1 and C-2. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
Structure
Thumb
Synonyms:
  • 1,2-Dimyristoyl-rac-glycero-3-phosphoethanolamine
  • 1,2-ditetradecanoyl-rac-glycero-3-phosphoethanolamine
  • 1-phosphatidylethanolamine
  • O-(1-β-acyl-2-acyl-sn-glycero-3-phospho)-ethanolamine
  • A 1-phosphatidylethanolamine
  • A phosphatidylethenolamine
  • An L-1-phosphotidylethanolamine
  • Glycerophosphoethanolamine
  • GPEtn(14:0/14:0)
  • GPEtn(28:0)
  • L-1-phosphotidylethanolamine
  • O-(1-β-acyl-2-acyl-sn-glycero-3-phospho)-ethanolamine
  • PE(14:0/14:0)
  • PE(28:0)
  • Phophatidylethanolamine(14:0/14:0)
  • Phophatidylethanolamine(28:0)
  • Phosphatidylethanolamine
  • Phosphatidylethanolamine (ecoli)
  • PtdEtn
Chemical Formula: C33H66NO8P
Average Molecular Weight: 635.8528
Monoisotopic Molecular Weight: 635.452604605
InChI Key: NEZDNQCXEZDCBI-WJOKGBTCSA-N
InChI:InChI=1S/C33H66NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-32(35)39-29-31(30-41-43(37,38)40-28-27-34)42-33(36)26-24-22-20-18-16-14-12-10-8-6-4-2/h31H,3-30,34H2,1-2H3,(H,37,38)/t31-/m1/s1
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2,3-bis(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy((2R)-2,3-bis(tetradecanoyloxy)propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent Phosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000205 mg/mLALOGPS
logP7.06ALOGPS
logP8.67ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 Å2ChemAxon
Rotatable Bond Count35ChemAxon
Refractivity172.6 m3·mol-1ChemAxon
Polarizability76.48 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
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
Adenosine triphosphate + Water + PE(14:0/14:0) > ADP + Hydrogen ion + Phosphate + PE(14:0/14:0)
Adenosine triphosphate + Water + PE(14:0/14:0) > ADP + Hydrogen ion + Phosphate + PE(14:0/14:0)
-->-->-->-->-->-->-->-->-->-->-->-->2 S-Adenosylmethionine + PE(14:0/14:0) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylethanolamine (dihexadec-9,10-cyclo-anoyl, N-C16:0 cyclo) +2 Hydrogen ion
2 S-Adenosylmethionine + PE(14:0/14:0) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylethanolamine (dioctadec-11,12-cyclo-anoyl, N-C18:0 cyclo) +2 Hydrogen ion
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Adenosine triphosphate + Dodecanoate (N-C12:0) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + Adenosine triphosphate + tetradecanoate (n-C14:0) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + Adenosine triphosphate + Tetradecenoate (N-C14:1) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Adenosine triphosphate + Palmitic acid > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Adenosine triphosphate + Octadecanoate (N-C18:0) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Adenosine triphosphate + Octadecenoate (N-C18:1) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphoethanolamine KDO(2)-lipid (A)
KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Phosphoethanolamine KDO(2)-lipid (A)
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + Hydrogen ion + tetradecanoate (n-C14:0)
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + Hydrogen ion + Tetradecenoate (N-C14:1)
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Hydrogen ion + Palmitic acid
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Hydrogen ion + Octadecanoate (N-C18:0)
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Hydrogen ion + Octadecenoate (N-C18:1)
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + Hydrogen ion + tetradecanoate (n-C14:0)
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + Hydrogen ion + Tetradecenoate (N-C14:1)
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Hydrogen ion + Palmitic acid
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Hydrogen ion + Octadecanoate (N-C18:0)
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Hydrogen ion + Octadecenoate (N-C18:1)
Hydrogen ion + PS(16:0/16:0) <> Carbon dioxide + PE(14:0/14:0)
PE(14:0/14:0) + Water <> 2-Acyl-sn-glycero-3-phosphoethanolamine + Fatty acid
PS(16:0/16:0) <> PE(14:0/14:0) + Carbon dioxide
Acyl-[acyl-carrier protein] + 2-Acyl-sn-glycero-3-phosphoethanolamine + Acyl-[acyl-carrier protein] <> Acyl-carrier protein + PE(14:0/14:0) + Acyl-carrier protein
PE(14:0/14:0) + &alpha;-Kdo-(2->4)-&alpha;-Kdo-(2->6)-lipid IV<SUB>A</SUB> a 1,2-diacylglycerol + phosphatidylethanolamine-KDO<sub>2</sub>-lipidA
an L-1-phosphatidylserine + Hydrogen ion > PE(14:0/14:0) + Carbon dioxide
PE(14:0/14:0) + Water a fatty acid + a 2-lyso-phosphatidyl-ethanolamine + Hydrogen ion
PE(14:0/14:0) + Water > a 1-lyso-2-acyl-<i>sn</i>-glycero-3-phosphoethanolamine + a fatty acid + Hydrogen ion
PS(14:0/14:0) + Hydrogen ion > PE(14:0/14:0) + Carbon dioxide
PG(16:0/16:0) + PE(14:0/14:0) > Ethanolamine + CL(16:0/16:0/14:0/14:0)
PG(18:1(9Z)/16:0) + PE(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/16:0/14:0/14:0)
PG(18:1(9Z)/16:1(9Z)) + PE(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/16:1(9Z)/14:0/14:0)
PE(14:0/14:0) + PG(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/14:0/14:0/18:1(9Z))
PE(14:0/14:0) + PG(16:0/19:0cycw8c) > Ethanolamine + CL(19:0cycv8c/16:0/14:0/14:0)
PG(16:1(9Z)/14:0) + PE(14:0/14:0) > Ethanolamine + CL(19:0cycv8c/16:1(9Z)/14:0/14:0)
PG(19:iso/18:1(9Z)) + PE(14:0/14:0) > Ethanolamine + CL(19:0cycv8c/18:1(9Z)/14:0/14:0)
PE(14:0/14:0) + PG(18:1(9Z)/18:1(9Z)) > CL(18:1(9Z)/18:1(9Z)/14:0/14:0) + Ethanolamine
PG(18:1(9Z)/18:1(9Z)) + PE(14:0/14:0) > CL(18:1(9Z)/14:0/18:1(9Z)/14:0) + Ethanolamine
PE(14:0/14:0) + PG(10:0(3-OH)/17:0cycw7c) > Ethanolamine + CL(10:0(3-OH)/17:0cycw7c/14:0/14:0)
PG(14:0(3-OH)/17:0cycw7c) + PE(14:0/14:0) > Ethanolamine + CL(14:0(3-OH)/17:0cycw7c/14:0/14:0)
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9120302000-8fbb8bdc68d27155acf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9220110000-9e7c385e3e9ac321792dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9250120000-c02f43939ccb74ea4052View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ae9-1290313000-5ef301777e2a16f1bf25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-6591200000-4a080b6320f9a7b2fc1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9210000000-b9ee34dbfebf733936cbView 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 IDHMDB08821
Pubchem Compound ID9852308
Kegg IDC00350
ChemSpider ID8028021
WikipediaLecithin
BioCyc IDL-1-PHOSPHATIDYL-ETHANOLAMINE
EcoCyc IDL-1-PHOSPHATIDYL-ETHANOLAMINE

Enzymes

General function:
Involved in phosphatidylserine decarboxylase activity
Specific function:
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2)
Gene Name:
psd
Locus Tag:
PA4957
Molecular weight:
32 kDa
Reactions
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).
General function:
Involved in nucleotide binding
Specific function:
Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:
msbA
Locus Tag:
PA4997
Molecular weight:
66.4 kDa
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

General function:
Involved in nucleotide binding
Specific function:
Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:
msbA
Locus Tag:
PA4997
Molecular weight:
66.4 kDa
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaE
Locus Tag:
PA4455
Molecular weight:
28.4 kDa