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Record Information
Version	2.0
Creation Date	2015-09-08 19:01:42 -0600
Update Date	2015-09-14 11:20:03 -0600
Secondary Accession Numbers	ECMDB24322
Identification
Name:	PE(12:0/18:1(9Z))
Description	PE(12:0/18:1(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(12:0/18:1(9Z)), in particular, consists of one dodecanoyl 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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa89e3fc4> Close
Synonyms:	Not Available
Chemical Formula:	C35H68NO8P
Weight:	Average: 661.8901 Monoisotopic: 661.468254669
InChI Key:	FUUNMZKPCMPCHT-ILGKRYBBSA-N
InChI:	InChI=1S/C35H68NO8P/c1-3-5-7-9-11-13-14-15-16-17-18-20-22-24-26-28-35(38)44-33(32-43-45(39,40)42-30-29-36)31-41-34(37)27-25-23-21-19-12-10-8-6-4-2/h15-16,33H,3-14,17-32,36H2,1-2H3,(H,39,40)/b16-15-/t33-/m1/s1
CAS number:	Not Available
IUPAC Name:	(2-aminoethoxy)[(2R)-3-(dodecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name:	2-aminoethoxy((2R)-3-(dodecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
SMILES:	[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCC)COP(O)(=O)OCCN
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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Glycerophospholipids
Sub Class	Glycerophosphoethanolamines
Direct Parent	Phosphatidylethanolamines
Alternative Parents	Phosphoethanolamines Fatty acid esters Dialkyl phosphates Dicarboxylic acids and derivatives Carboxylic acid esters Amino acids and derivatives Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	Diacylglycerophosphoethanolamines (LMGP02011260 )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.00014 g/L ALOGPS logP 7.5 ALOGPS logP 9.2 ChemAxon logS -6.7 ALOGPS pKa (Strongest Acidic) 1.87 ChemAxon pKa (Strongest Basic) 10 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 134.38 Ų ChemAxon Rotatable Bond Count 36 ChemAxon Refractivity 182.92 m³·mol⁻¹ ChemAxon Polarizability 79.37 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0006-9231002000-57cac7531a77b7f742a6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0006-9330001000-a214922e84d5fbc73fbb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9260020000-5663790c96ea4810249f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-01qa-1932003000-7d170603823477b0247d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0035-3910000000-e10620a5d193d74e542b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9310000000-b2ff5ccd1bf276f9541f View 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
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 9547934 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available