PE(15:0/16:1(9Z)) (ECMDB24108) (M2MDB006225)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 17:49:22 -0600
Update Date2015-09-14 11:20:00 -0600
Secondary Accession Numbers
  • ECMDB24108
Identification
Name:PE(15:0/16:1(9Z))
DescriptionPE(15:0/16:1(9Z)) 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(15:0/16:1(9Z)), in particular, consists of one pentadecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
GPEtn(15:0/16:1)HMDB
1-Pentadecanoyl-2-palmitoleoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(31:1)HMDB
Phophatidylethanolamine(31:1)HMDB
PE(15:0/16:1)HMDB
GPEtn(31:1)HMDB
1-Pentadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(15:0/16:1)HMDB
PE(15:0/16:1(9Z))Lipid Annotator
Chemical Formula:C36H70NO8P
Weight:Average: 675.9167
Monoisotopic: 675.483904733
InChI Key:YMEQXDCYZVOOFR-NOLSVFIGSA-N
InChI:InChI=1S/C36H70NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)45-34(33-44-46(40,41)43-31-30-37)32-42-35(38)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13,15,34H,3-12,14,16-33,37H2,1-2H3,(H,40,41)/b15-13-/t34-/m1/s1
CAS number:Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name:2-aminoethoxy((2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCC
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentPhosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00011 g/LALOGPS
logP7.76ALOGPS
logP9.64ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity187.52 m³·mol⁻¹ChemAxon
Polarizability81.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
PS(16:0/16:1(9Z)) + Hydrogen ion > PE(15:0/16:1(9Z)) + Carbon dioxide
PE(15:0/16:1(9Z)) + PG(16:0/16:0) > Ethanolamine + CL(15:0cyclo/16:0/16:0/16:1(9Z))
PE(15:0/16:1(9Z)) + PG(16:0/16:0) > Ethanolamine + CL(15:0cyclo/16:0/16:1(9Z)/16:0)
PG(16:0/16:0) + PE(15:0/16:1(9Z)) > Ethanolamine + CL(15:0cyclo/16:1(9Z)/16:0/16:0)
PG(16:1(9Z)/16:1(9Z)) + PE(15:0/16:1(9Z)) > Ethanolamine + CL(15:0cyclo/16:1(9Z)/16:1(9Z)/16:1(9Z))
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/16:1(9Z)) > Ethanolamine + CL(15:0cyclo/18:1(9Z)/16:1(9Z)/18:1(9Z))
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/16:1(9Z)) > Ethanolamine + CL(15:0cyclo/18:1(9Z)/18:1(9Z)/16:1(9Z))
PG(16:0/16:0) + PE(15:0/16:1(9Z)) > CL(16:0/15:0cyclo/16:0/16:1(9Z)) + Ethanolamine
PG(16:0/16:0) + PE(15:0/16:1(9Z)) > Ethanolamine + CL(16:0/15:0cyclo/16:1(9Z)/16:0)
PG(16:0/16:0) + PE(15:0/16:1(9Z)) > CL(16:0/16:0/16:1(9Z)/15:0cyclo) + Ethanolamine
PE(15:0/16:1(9Z)) + PG(16:1(9Z)/16:1(9Z)) > CL(16:1(9Z)/15:0cyclo/16:1(9Z)/16:1(9Z)) + Ethanolamine
PG(18:1(9Z)/18:1(9Z)) + PE(15:0/16:1(9Z)) > Ethanolamine + CL(16:1(9Z)/15:0cyclo/18:1(9Z)/18:1(9Z))
SMPDB Pathways:
phospholipid biosynthesis CL(15:0cyclo/16:0/16:0/16:1(9Z))PW001102 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:0/16:1(9Z)/16:0)PW001106 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:0/16:0)PW001124 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/16:1(9Z))PW001129 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/16:1(9Z)/18:1(9Z))PW001168 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/16:1(9Z))PW001175 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/15:0cyclo/16:0/16:1(9Z))PW001227 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/15:0cyclo/16:1(9Z)/16:0)PW001232 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:0/16:1(9Z)/15:0cyclo)PW001261 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))PW001330 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:1(9Z)/16:1(9Z))PW001453 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/18:1(9Z)/18:1(9Z))PW001462 ThumbThumb?image type=greyscaleThumb?image type=simple
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_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0030009000-5bb3e08d4ed96a8f62eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0030009000-5bb3e08d4ed96a8f62eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ukc-0190303000-85224f8ab5ff299d3b66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000019000-2400c1ea5589298fe31aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0011697000-2fbfcb5107a451cfb81aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0011693000-ffbf4a408345f79f34f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000019000-6582f01391888cbd6c99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0011697000-3f4276cc8e819262fda3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0011693000-f083f287c66762eb2a6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0030009000-8657eabd07f7aa995b29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0030009000-8657eabd07f7aa995b29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ukc-0190303000-3e9ff255560bb82f9cd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000019000-761ed3632735971bd7f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0000019000-3ae671c014c6371365c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0100219000-8284422e284f7e54c236View 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 IDHMDB0008891
Pubchem Compound ID52924932
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Phosphatidylserine decarboxylase proenzyme
General function:
Involved in phosphatidylserine decarboxylase activity
Specific function:
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2)
Gene Name:
psd
Uniprot ID:
P0A8K1
Molecular weight:
35934
Reactions
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).
Protein Details
2. Cardiolipin synthase C
General function:
cardiolipin biosynthetic process
Specific function:
Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) from phosphatidylglycerol (PG) and phosphatidylethanolamine (PE).
Gene Name:
clsC
Uniprot ID:
P75919
Molecular weight:
53665
Reactions
Phosphatidylglycerol + phosphatidylethanolamine = diphosphatidylglycerol + ethanolamine