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PE(18:1(9Z)/18:1(9Z)) (YMDB01208)

Identification
YMDB IDYMDB01208
NamePE(18:1(9Z)/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
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
  • (3-Phosphatidyl)-ethanolamine
  • (3-Phosphatidyl)ethanolamine
  • 1-Acyl-2-acyl-sn-glycero-3-phosphoethanolamine
  • 1,2-diacyl-sn-glycero-3-phosphoethanolamine
  • 1,2-dioleoyl-rac-glycero-3-phosphoethanolamine
  • Cephalin
  • GPEtn(18:1/18:1)
  • GPEtn(18:1n9/18:1n9)
  • GPEtn(18:1w9/18:1w9)
  • GPEtn(36:2)
  • O-(1-beta-Acyl-2-acyl-sn-glycero-3-phospho)ethanolamine
  • PE(18:1/18:1)
  • PE(18:1n9/18:1n9)
  • PE(18:1w9/18:1w9)
  • PE(36:2)
  • Phophatidylethanolamine(18:1/18:1)
  • Phophatidylethanolamine(18:1n9/18:1n9)
  • Phophatidylethanolamine(18:1w9/18:1w9)
  • Phophatidylethanolamine(36:2)
  • Phosphatidylethanolamine
  • phosphatidylethanolamines
  • 1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine
  • 1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoethanolamine zwitterion
  • 1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylethanolamine zwitterion
  • 1,2-Dioleoylphosphatidylethanolamine
  • 1,2-DOPE
  • 1,2-Dielaidoylphosphatidylethanolamine
  • 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine
  • 1-2-DOPE
  • Lipofectin
  • Dioleoyl cephalin
  • 1,2-Dioleoylglycero-3-phosphoethanolamine
  • 1-2-Di-(9-octadecenoyl)-sn-glycero-3-phosphoethethanolamine
  • 1,2-Di(9Z-octadecenoyl)-rac-glycero-3-phosphoethanolamine
  • PE(18:1(9Z)/18:1(9Z))
CAS number2462-63-7
WeightAverage: 744.048
Monoisotopic: 743.546505474
InChI KeyMWRBNPKJOOWZPW-NYVOMTAGSA-N
InChIInChI=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
IUPAC Name(2-aminoethoxy)[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name1,2-dioleoyl-sn-gl
Chemical FormulaC41H78NO8P
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(18:1(9Z)/18:1(9Z))PW002788 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(18:1(9Z)/18:1(9Z))PW002796 ThumbThumb?image type=greyscaleThumb?image type=simple
Phosphatidylcholine biosynthesis PC(18:1(9Z)/18:1(9Z))PW002941 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Glycosylphosphatidylinositol(GPI)-anchor biosynthesisec00563 Map00563
SMPDB Reactions
PE(18:1(9Z)/18:1(9Z)) + S-Adenosyl-L-methionine → PE-NMe(18:1(9Z)/18:1(9Z)) + hydron + S-Adenosylhomocysteine
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-001l-0090100400-2e505f9bbb1be20750d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 2V, positivesplash10-0006-0000001900-5c8d87e0015e6e5d1cb9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0006-0000003900-f9393f34f408d3df66f5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 6V, positivesplash10-0f6x-0000005900-0c0762234af9b7f2c3b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 8V, positivesplash10-0f6x-0001007900-cadb26b1db0ca86589e5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 14V, positivesplash10-0udi-0101009200-7fcb84a56ede0e704634JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 16V, positivesplash10-0udi-0001009100-5aeac3a5eb6fed78d9a2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-0udi-0000009200-86abb6550ab0e0c580fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0006-0000002900-af4784d2becf4f36e733JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-0udi-0000009200-240a0652b33b213f4a7eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 43V, positivesplash10-0udi-0000009000-fcccd79c5013049d21a8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 55V, positivesplash10-0udi-1111009000-a46540873bbf27bb32fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 65V, positivesplash10-0uxs-9831005000-b52b90c60bc5216ef312JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 77V, positivesplash10-015a-9600000000-d5b92aa6c5d21aff830aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 87V, positivesplash10-00ls-9500000000-aa5703b09a2b4982f7e1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 99V, positivesplash10-015a-9300000000-c887c51891d1740cd6f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 110V, positivesplash10-015a-9200000000-97aea4999fbe0d5dd12aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 132V, positivesplash10-067i-9100000000-4ba5915c8412373ceb4aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 52V, positivesplash10-0udi-0000009000-90677bb4d4cb194d7bb8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0010000900-994357b6692ae6b01544JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0010000900-994357b6692ae6b01544JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-0390300600-ac1e6f12f1f2dd8e7274JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-cbb310d334ec991a7d65JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0001309700-eeb33a57ed592ba6ec54JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0001309300-02a1479ca6e84ae12d27JSpectraViewer
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
  • Smolka, M. B., Albuquerque, C. P., Chen, S. H., Zhou, H. (2007). "Proteome-wide identification of in vivo targets of DNA damage checkpoint kinases." Proc Natl Acad Sci U S A 104:10364-10369.17563356
  • Lee, K. S., Patton, J. L., Fido, M., Hines, L. K., Kohlwein, S. D., Paltauf, F., Henry, S. A., Levin, D. E. (1994). "The Saccharomyces cerevisiae PLB1 gene encodes a protein required for lysophospholipase and phospholipase B activity." J Biol Chem 269:19725-19730.8051052
  • Chi, A., Huttenhower, C., Geer, L. Y., Coon, J. J., Syka, J. E., Bai, D. L., Shabanowitz, J., Burke, D. J., Troyanskaya, O. G., Hunt, D. F. (2007). "Analysis of phosphorylation sites on proteins from Saccharomyces cerevisiae by electron transfer dissociation (ETD) mass spectrometry." Proc Natl Acad Sci U S A 104:2193-2198.17287358
  • Gruhler, A., Olsen, J. V., Mohammed, S., Mortensen, P., Faergeman, N. J., Mann, M., Jensen, O. N. (2005). "Quantitative phosphoproteomics applied to the yeast pheromone signaling pathway." Mol Cell Proteomics 4:310-327.15665377
  • Albuquerque, C. P., Smolka, M. B., Payne, S. H., Bafna, V., Eng, J., Zhou, H. (2008). "A multidimensional chromatography technology for in-depth phosphoproteome analysis." Mol Cell Proteomics 7:1389-1396.18407956
  • Hjelmstad, R. H., Bell, R. M. (1988). "The sn-1,2-diacylglycerol ethanolaminephosphotransferase activity of Saccharomyces cerevisiae. Isolation of mutants and cloning of the EPT1 gene." J Biol Chem 263:19748-19757.2848840
  • Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
  • Kodaki, T., Yamashita, S. (1987). "Yeast phosphatidylethanolamine methylation pathway. Cloning and characterization of two distinct methyltransferase genes." J Biol Chem 262:15428-15435.2445736
  • Li, X., Gerber, S. A., Rudner, A. D., Beausoleil, S. A., Haas, W., Villen, J., Elias, J. E., Gygi, S. P. (2007). "Large-scale phosphorylation analysis of alpha-factor-arrested Saccharomyces cerevisiae." J Proteome Res 6:1190-1197.17330950
  • Yamashita, S., Nikawa, J. (1997). "Phosphatidylserine synthase from yeast." Biochim Biophys Acta 1348:228-235.9370337
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16038
HMDB IDHMDB09059
Pubchem Compound ID6437392
Kegg IDC00350
ChemSpider ID7825707
FOODB IDFDB026249
WikipediaLecithin
BioCyc IDL-1-PHOSPHATIDYL-ETHANOLAMINE

Enzymes

Protein Details
1. Phosphatidylethanolamine N-methyltransferase
General function:
Involved in phosphatidylethanolamine N-methyltransferas
Specific function:
S-adenosyl-L-methionine + phosphatidylethanolamine = S-adenosyl-L-homocysteine + phosphatidyl-N-methylethanolamine
Gene Name:
PEM1
Uniprot ID:
P05374
Molecular weight:
101203.0
Reactions
S-adenosyl-L-methionine + phosphatidylethanolamine → S-adenosyl-L-homocysteine + phosphatidyl-N-methylethanolamine.