PE(18:1(9Z)/18:1(9Z)) (ECMDB24127) (M2MDB006244)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 17:49:31 -0600
Update Date2015-09-14 11:20:00 -0600
Secondary Accession Numbers
  • ECMDB24127
Identification
Name:PE(18:1(9Z)/18:1(9Z))
DescriptionPE(18:1(9Z)/18:1(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 positions. PE(18:1(9Z)/18:1(9Z)), in particular, consists of two 9Z-octadecenoyl 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
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineChEBI
1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylethanolamine zwitterionChEBI
1,2-DioleoylphosphatidylethanolamineHMDB
1,2-DOPEHMDB
1,2-DielaidoylphosphatidylethanolamineHMDB
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamineHMDB
1-2-DOPEHMDB
LipofectinHMDB
Dioleoyl cephalinHMDB
1,2-Dioleoylglycero-3-phosphoethanolamineHMDB
1-2-Di-(9-octadecenoyl)-sn-glycero-3-phosphoethethanolamineHMDB
1,2-Dioleoyl-rac-glycero-3-phosphoethanolamineHMDB
PE(18:1/18:1)HMDB
GPEtn(18:1/18:1)HMDB
Phophatidylethanolamine(36:2)HMDB
Phophatidylethanolamine(18:1/18:1)HMDB
GPEtn(36:2)HMDB
1,2-Di(9Z-octadecenoyl)-rac-glycero-3-phosphoethanolamineHMDB
PE(36:2)HMDB
PE(18:1(9Z)/18:1(9Z))Lipid Annotator
Chemical Formula:C41H78NO8P
Weight:Average: 744.0337
Monoisotopic: 743.546504989
InChI Key:MWRBNPKJOOWZPW-NYVOMTAGSA-N
InChI:InChI=1S/C41H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,39H,3-16,21-38,42H2,1-2H3,(H,45,46)/b19-17-,20-18-/t39-/m1/s1
CAS number:Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name:1,2-dioleoyl-sn-gl
SMILES:[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC
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 Solubility6.1e-05 g/LALOGPS
logP8.81ALOGPS
logP11.51ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity211.64 m³·mol⁻¹ChemAxon
Polarizability90.54 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
PS(18:1(9Z)/18:1(9Z)) + Hydrogen ion > PE(18:1(9Z)/18:1(9Z)) + Carbon dioxide
PG(14:0/14:0) + PE(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(14:0/18:1(9Z)/14:0/18:1(9Z))
PG(15:0cyclo/14:0(3-OH)) + PE(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(15:0cyclo/14:0/18:1(9Z)/18:1(9Z))
PE(18:1(9Z)/18:1(9Z)) + PG(16:0/16:0) > Ethanolamine + CL(16:0/16:0/18:1(9Z)/18:1(9Z))
PG(16:0/16:0) + PE(18:1(9Z)/18:1(9Z)) > CL(16:0/18:1(9Z)/16:0/18:1(9Z)) + Ethanolamine
PE(18:1(9Z)/18:1(9Z)) + PG(16:0/16:0) > Ethanolamine + CL(16:0/18:1(9Z)/18:1(9Z)/16:0)
PG(16:0/16:1(9Z)) + PE(18:1(9Z)/18:1(9Z)) > CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z)) + Ethanolamine
PG(16:1(9Z)/16:1(9Z)) + PE(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + PE(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:1(9Z))
PE(16:1(9Z)/17:0) + PE(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/18:1(9Z)/17:0cycw7c/18:1(9Z))
PG(16:1(9Z)/16:1(9Z)) + PE(18:1(9Z)/18:1(9Z)) > CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:1(9Z)) + Ethanolamine
PE(18:1(9Z)/18:1(9Z)) + PG(18:1(9Z)/16:0) > Ethanolamine + CL(18:1(9Z)/16:0/18:1(9Z)/18:1(9Z))
PE(18:1(9Z)/18:1(9Z)) + PG(18:1(9Z)/16:1(9Z)) > Ethanolamine + CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))
PE(18:1(9Z)/18:1(9Z)) + PG(15:0/17:0cycw7c) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/18:1(9Z)/17:0cycw7c)
PE(18:1(9Z)/18:1(9Z)) + PG(15:0/17:0cycw7c) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/17:0cycw7c/18:1(9Z))
SMPDB Pathways:
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/17:0cycw7c/18:1(9Z)))PW001529 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/18:1(9Z)/17:0cycw7c))PW001534 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/16:0/18:1(9Z)/18:1(9Z)))PW001596 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z)))PW001622 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/14:0/18:1(9Z))PW001046 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/14:0/18:1(9Z)/18:1(9Z))PW001057 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))PW001283 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))PW001360 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:0)PW001368 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z))PW001369 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))PW001549 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:1(9Z))PW001576 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))PW001602 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 (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-001l-0090100400-2e505f9bbb1be20750d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 2V, positivesplash10-0006-0000001900-5c8d87e0015e6e5d1cb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0006-0000003900-f9393f34f408d3df66f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 6V, positivesplash10-0f6x-0000005900-0c0762234af9b7f2c3b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 8V, positivesplash10-0f6x-0001007900-cadb26b1db0ca86589e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 14V, positivesplash10-0udi-0101009200-7fcb84a56ede0e704634View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 16V, positivesplash10-0udi-0001009100-5aeac3a5eb6fed78d9a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-0udi-0000009200-86abb6550ab0e0c580fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0006-0000002900-af4784d2becf4f36e733View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-0udi-0000009200-240a0652b33b213f4a7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 43V, positivesplash10-0udi-0000009000-fcccd79c5013049d21a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 55V, positivesplash10-0udi-1111009000-a46540873bbf27bb32fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 65V, positivesplash10-0uxs-9831005000-b52b90c60bc5216ef312View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 77V, positivesplash10-015a-9600000000-d5b92aa6c5d21aff830aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 87V, positivesplash10-00ls-9500000000-aa5703b09a2b4982f7e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 99V, positivesplash10-015a-9300000000-c887c51891d1740cd6f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 110V, positivesplash10-015a-9200000000-97aea4999fbe0d5dd12aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 132V, positivesplash10-067i-9100000000-4ba5915c8412373ceb4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 52V, positivesplash10-0udi-0000009000-90677bb4d4cb194d7bb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0010000900-994357b6692ae6b01544View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0010000900-994357b6692ae6b01544View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-0390300600-ac1e6f12f1f2dd8e7274View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-cbb310d334ec991a7d65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0001309700-eeb33a57ed592ba6ec54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0001309300-02a1479ca6e84ae12d27View 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 ID74986
HMDB IDHMDB0009059
Pubchem Compound ID9546757
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