Record Information
Version2.0
Creation Date2012-10-24 09:54:30 -0600
Update Date2015-09-14 11:19:53 -0600
Secondary Accession Numbers
  • ECMDB23512
Identification
Name:PE(17:0cycw7c/19:iso)
DescriptionPE(17:0cycw7c/19:iso) 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(17:0cycw7c/19:iso), in particular, consists of one heptadec-9-10-cyclo-anoyl chain to the C-1 atom, and one 17-methylocatdecanoyl 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
Synonyms:
  • 1-heptadec-9-10-cyclo-anoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoethanolamine
  • 1-heptadec-9-10-cyclo-anoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoethanolamine
  • GPEtn(17:0/19:0)
  • GPEtn(36:0)
  • PE(17:0/19:0)
  • PE(36:0)
  • Phophatidylethanolamine(17:0/19:0)
  • Phophatidylethanolamine(36:0)
Chemical Formula:C41H80NO8P
Weight:Average: 746.0496
Monoisotopic: 745.562155053
InChI Key:OUFPRNQGNZRVAR-DFCGPKRUSA-N
InChI:InChI=1S/C41H80NO8P/c1-4-5-6-22-27-37-33-38(37)28-23-18-16-20-24-29-40(43)47-34-39(35-49-51(45,46)48-32-31-42)50-41(44)30-25-19-15-13-11-9-7-8-10-12-14-17-21-26-36(2)3/h36-39H,4-35,42H2,1-3H3,(H,45,46)/t37?,38?,39-/m1/s1
CAS number:Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(17-methyloctadecanoyl)oxy]propoxy]phosphinic acid
Traditional IUPAC Name:2-aminoethoxy((2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid
SMILES:CCCCCCC1CC1CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCC(C)C
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
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.3e-05 g/LALOGPS
logP8.33ALOGPS
logP11.29ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity207.45 m³·mol⁻¹ChemAxon
Polarizability91.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
phospholipid biosynthesis (CL(17:0cycw7c/19:0cycv8c/14:0/14:0))PW001475 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/17:0cycw7c/14:0/14:0))PW001397 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/19:0cycv8c/14:0/17:0cycw7c)PW001050 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/19:0cycv8c/17:0cycw7c/14:0)PW001052 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/17:0cycw7c/19:0cycv8c)PW001543 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/19:0cycv8c/17:0cycw7c)PW001555 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/19:0cycv8c/19:0cycv8c)PW001570 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/16:1(9Z)/17:0cycw7c)PW001625 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/17:0cycw7c/16:1(9Z))PW001627 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/17:0cycw7c/19:0cycv8c)PW001631 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/17:0cycw7c)PW001642 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9040200200-3666e89b139fc0f02b9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9140000000-47cc6d713637c823ffccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9052000000-a16f55a007149eb3cd72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-0190200200-61022e42adfbd43721bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ov-4390100000-e84114fed6928eff0be4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-5e83c18bf3bcdc98d744View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Casadei MA, Mañas P, Niven G, Needs E, Mackey BM. (2002) "Role of membrane fluidity in pressure resistance of Escherichia coli NCTC 8164." Appl Environ Microbiol. 68(12):5965-72. Pubmed: 12450817
  • 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
  • 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 IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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).
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
Gene Name:
aas
Uniprot ID:
P31119
Molecular weight:
80699
Reactions
Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine.
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein].
General function:
Not Available
Specific function:
Not known; overproduction leads to camphor resistance and chromosome condensation
Gene Name:
crcA
Uniprot ID:
P37001
Molecular weight:
21770
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

Transporters

General function:
Involved in phospholipid transporter activity
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaB
Uniprot ID:
P64602
Molecular weight:
10680
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaD
Uniprot ID:
P64604
Molecular weight:
19576
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaE
Uniprot ID:
P64606
Molecular weight:
27863