PE(18:0/18:1(9Z)) (YMDB01206)

Identification
YMDB IDYMDB01206
NamePE(18:0/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE(18:0/18:1(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 atoms. PE(18:0/18:1(9Z)), in particular, consists of one octadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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
  • (3-Phosphatidyl)-ethanolamine
  • (3-Phosphatidyl)ethanolamine
  • 1-Acyl-2-acyl-sn-glycero-3-phosphoethanolamine
  • 1-stearoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine
  • 1,2-diacyl-sn-glycero-3-phosphoethanolamine
  • Cephalin
  • GPEtn(18:0/18:1)
  • GPEtn(18:0/18:1n9)
  • GPEtn(18:0/18:1w9)
  • GPEtn(36:1)
  • O-(1-beta-Acyl-2-acyl-sn-glycero-3-phospho)ethanolamine
  • PE(18:0/18:1)
  • PE(18:0/18:1n9)
  • PE(18:0/18:1w9)
  • PE(36:1)
  • Phophatidylethanolamine(18:0/18:1)
  • Phophatidylethanolamine(18:0/18:1n9)
  • Phophatidylethanolamine(18:0/18:1w9)
  • Phophatidylethanolamine(36:1)
  • Phosphatidylethanolamine
  • phosphatidylethanolamines
  • 1-Octadecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoethanolamine
  • 1-Octadecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoethanolamine zwitterion
  • 1-Stearoyl-2-oleoyl-gpe
  • 1-Stearoyl-2-oleoyl-gpe (18:0/18:1)
  • 2-Azaniumylethyl (2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(stearoyloxy)propyl phosphate
  • GPE(18:0/18:1)
  • PE 18:0/18:1(omega-9)
  • 2-Azaniumylethyl (2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(stearoyloxy)propyl phosphoric acid
  • 1-Octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine
  • 1-Stearoyl-2-oleoyl-phosphatidyethanolamine
  • 1-Stearoyl-2-oleoyl-sn-glycero-phosphatidylethanolamine
  • 1-Stearoyl-2-oleoyl-sn-glycerol-3-phosphoethanolamine
  • 1-Stearoyl-2-oleoylglycero-3-phosphorylethanolamine
  • 1-Stearoyl-2-oleoylphosphatidylethanolamine
  • GPE(18:0/18:1(9Z))
  • GPE(18:0/18:1n9)
  • GPE(18:0/18:1W9)
  • GPE(36:1)
  • GPEtn(18:0/18:1(9Z))
  • Phosphatidylethanolamine(18:0/18:1(9Z))
  • Phosphatidylethanolamine(18:0/18:1)
  • Phosphatidylethanolamine(18:0/18:1n9)
  • Phosphatidylethanolamine(18:0/18:1W9)
  • Phosphatidylethanolamine(36:1)
  • SOPE
  • PE(18:0/18:1(9Z))
CAS numberNot Available
WeightAverage: 746.064
Monoisotopic: 745.562155538
InChI KeyJQKOHRZNEOQNJE-DJEJVYNPSA-N
InChIInChI=1S/C41H80NO8P/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/h18,20,39H,3-17,19,21-38,42H2,1-2H3,(H,45,46)/b20-18-/t39-/m1/s1
IUPAC Name(2-aminoethoxy)[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy)phosphinic acid
Chemical FormulaC41H80NO8P
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(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 Solubility5.5e-05 g/LALOGPS
logP8.83ALOGPS
logP11.87ChemAxon
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 Count42ChemAxon
Refractivity210.52 m³·mol⁻¹ChemAxon
Polarizability92.13 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
Phosphatidylcholine biosynthesis PC(18:0/18:1(9Z))PW002945 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Glycosylphosphatidylinositol(GPI)-anchor biosynthesisec00563 Map00563
SMPDB Reactions
PE(18:0/18:1(9Z)) + S-Adenosyl-L-methionine → PE-NMe(18:0/18:1(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 (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-004i-0002349700-ec82ed0595ac526a01dfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0030000900-e1433848e477fac7af44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0030000900-e1433848e477fac7af44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0190300300-fefe4f5fc193387aa4c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-7176fc363ec50a2c3ca5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0003609700-dc3a90d8c00fc700c19eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003609300-df188d78672ea420fee7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0030000900-d7cda9257d10bafa2de3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0030000900-d7cda9257d10bafa2de3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0190300300-1b7bf283e64a78c2f788JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-f16c013a0ef8ad1e73b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0003609700-811a9e21167adc7d820eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003609300-af7611beccef54e97695JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000001900-5c10bab26c2e0a3f80b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-0000001900-607ffbebec54dace7f08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100201900-5f19400f5578875416d7JSpectraViewer
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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16038
HMDB IDHMDB08993
Pubchem Compound ID9546734
Kegg IDC00350
ChemSpider ID7825692
FOODB IDFDB026183
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.