PE(14:0/17:0cycw7c) (PAMDB002006)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB002006
Identification
Name: PE(14:0/17:0cycw7c)
Description:PE(14:0/17:0cycw7c) 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 atoms. PE(14:0/17:0cycw7c), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one heptadec-9-10-cyclo-anoyl to the C-2 atom. 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-myristoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phosphoethanolamine
  • 1-myristoyl-2-heptadec-cyclopropanol-sn-glycero-3-phosphoethanolamine
  • 1-tetradecanoyl-2-heptadec-9-10-cyclo-anoyl-sn-glycero-3-phosphoethanolamine
  • 1-tetradecanoyl-2-NULL-sn-glycero-3-phosphoethanolamine
  • GPEtn(14:0/17:0)
  • GPEtn(31:0)
  • PE(14:0/17:0)
  • PE(31:0)
  • Phophatidylethanolamine(14:0/17:0)
  • Phophatidylethanolamine(31:0)
Chemical Formula: C36H70NO8P
Average Molecular Weight: 675.9167
Monoisotopic Molecular Weight: 675.483904733
InChI Key: XZKIADFNBVEUKL-NGYOKKRJSA-N
InChI:InChI=1S/C36H70NO8P/c1-3-5-7-9-10-11-12-13-14-17-21-25-35(38)42-30-34(31-44-46(40,41)43-28-27-37)45-36(39)26-22-18-15-16-20-24-33-29-32(33)23-19-8-6-4-2/h32-34H,3-31,37H2,1-2H3,(H,40,41)/t32?,33?,34-/m1/s1
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-(tetradecanoyloxy)propoxyphosphinic acid
SMILES:CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCC1CC1CCCCCC
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
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Amine
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.71e-05 mg/mLALOGPS
logP7.44ALOGPS
logP9.23ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 Å2ChemAxon
Rotatable Bond Count36ChemAxon
Refractivity184.5 m3·mol-1ChemAxon
Polarizability81.41 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
PS(14:0/18:0) + Hydrogen ion > Carbon dioxide + PE(14:0/17:0cycw7c)
PS(14:0/17:0) + Hydrogen ion > PE(14:0/17:0cycw7c) + Carbon dioxide
PS(14:0(3-OH)/17:0cycw7c) + Hydrogen ion > PE(14:0/17:0cycw7c) + Carbon dioxide
PG(14:0(3-OH)/15:0) + PE(14:0/17:0cycw7c) > Ethanolamine + CL(14:0/15:0cyclo/14:0/17:0cycw7c)
PG(15:0cyclo/14:0(3-OH)) + PE(14:0/17:0cycw7c) > CL(15:0cyclo/14:0/17:0cycw7c/14:0) + Ethanolamine
PE(14:0/17:0cycw7c) + PG(16:0/16:0) > Ethanolamine + CL(16:0/16:0/14:0/17:0cycw7c)
PG(16:0/16:0) + PE(14:0/17:0cycw7c) > Ethanolamine + CL(16:0/16:0/17:0cycw7c/14:0)
PG(16:0/16:0) + PE(14:0/17:0cycw7c) > CL(16:0/17:0cycw7c/14:0/16:0) + Ethanolamine
PE(14:0/17:0cycw7c) + PG(16:0/16:0) > Ethanolamine + CL(16:0/17:0cycw7c/16:0/14:0)
PE(14:0/17:0cycw7c) + PG(16:1(9Z)/16:1(9Z)) > CL(16:1(9Z)/16:1(9Z)/14:0/17:0cycw7c) + Ethanolamine
PG(16:1(9Z)/16:1(9Z)) + PE(14:0/17:0cycw7c) > CL(16:1(9Z)/16:1(9Z)/17:0cycw7c/14:0) + Ethanolamine
PG(16:1(9Z)/16:1(9Z)) + PE(14:0/17:0cycw7c) > Ethanolamine + CL(16:1(9Z)/17:0cycw7c/14:0/16:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + PE(14:0/17:0cycw7c) > CL(16:1(9Z)/17:0cycw7c/16:1(9Z)/14:0) + Ethanolamine
PG(16:0/16:0) + PE(14:0/17:0cycw7c) > Ethanolamine + CL(17:0cycw7c/16:0/14:0/16:0)
PG(16:0/16:0) + PE(14:0/17:0cycw7c) > CL(17:0cycw7c/16:0/16:0/14:0) + Ethanolamine
PG(16:1(9Z)/16:1(9Z)) + PE(14:0/17:0cycw7c) > Ethanolamine + CL(17:0cycw7c/16:1(9Z)/14:0/16:1(9Z))
PE(14:0/17:0cycw7c) + PG(18:1(9Z)/14:0(3-OH)) > Ethanolamine + CL(18:1(9Z)/14:0/14:0/17:0cycw7c)
PG(18:1(9Z)/18:1(9Z)) + PE(14:0/17:0cycw7c) > Ethanolamine + CL(17:0cycw7c/18:1(9Z)/18:1(9Z)/14:0)
PG(18:1(9Z)/18:1(9Z)) + PE(14:0/17:0cycw7c) > Ethanolamine + CL(18:1(9Z)/18:1(9Z)/14:0/17:0cycw7c)
PE(14:0/17:0cycw7c) + PG(19:0cycv8c/14:0(3-OH)) > Ethanolamine + CL(19:0cycv8c/14:0/14:0/17:0cycw7c)
PE(14:0/17:0cycw7c) + PG(19:0cycv8c/19:iso) > CL(19:0cycv8c/19:0cycv8c/17:0cycw7c/14:0) + Ethanolamine
PG(19:0cycv8c/19:iso) + PE(14:0/17:0cycw7c) > CL(19:0cycv8c/19:0cycv8c/14:0/17:0cycw7c) + Ethanolamine
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9140202000-3ff90576c929c382318bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9230001000-16ac95bb589a28687c91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9260011000-9b73de0070fe3dd6a7ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-0190203000-75779998093c93291664View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5490100000-23ab19593541c0633e31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-fd1a3743190f4da93a00View 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
  • Oursel, D., Loutelier-Bourhis, C., Orange, N., Chevalier, S., Norris, V., Lange, C. M. (2007). "Lipid composition of membranes of Escherichia coli by liquid chromatography/tandem mass spectrometry using negative electrospray ionization." Rapid Commun Mass Spectrom 21:1721-1728. Pubmed: 17477452
  • 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 IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
• Phosphatidylserine decarboxylase proenzyme
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).

Transporters

Protein Details
• Probable phospholipid ABC transporter permease protein mlaE
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