PE(14:0(3-OH)/19:0cycv8c) (PAMDB003877)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB003877
Identification
Name: PE(14:0(3-OH)/19:0cycv8c)
Description:PE(14:0(3-OH)/19:0cycv8c) 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(14:0(3-OH)/19:0cycv8c), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one heptadec-11-12-cyclo-anoyl 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-3-hydroxytetradecanoyl-2-(heptadec-11-12-cyclo-anoyl)-sn-glycero-3-phosphoethanolamine
  • 1-3-hydroxytetradecanoyl-2-(heptadec-11-12-cyclo-anoyl)-sn-glycero-3-phosphoethanolamine
  • 1-3-hydroxytetradecanoyl-2-heptadec-11-12-cyclo-anoyl-sn-glycero-3-phosphoethanolamine
  • GPEtn(14:0/19:0)
  • GPEtn(33:0)
  • PE(14:0/19:0)
  • PE(33:0)
  • Phophatidylethanolamine(14:0/19:0)
  • Phophatidylethanolamine(33:0)
Chemical Formula: C38H74NO9P
Average Molecular Weight: 719.9692
Monoisotopic Molecular Weight: 719.510119483
InChI Key: ZROXBWUGINDXRR-VUCGXSAYSA-N
InChI:InChI=1S/C38H74NO9P/c1-3-5-7-9-10-11-14-17-21-25-35(40)30-38(42)45-31-36(32-47-49(43,44)46-28-27-39)48-37(41)26-22-18-15-12-13-16-20-24-34-29-33(34)23-19-8-6-4-2/h33-36,40H,3-32,39H2,1-2H3,(H,43,44)/t33?,34?,35?,36-/m1/s1
CAS number: Not Available
IUPAC Name:(2-aminoethoxy)[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphinic acid
Traditional IUPAC Name: 2-aminoethoxy((2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(3-hydroxytetradecanoyl)oxy]propoxy)phosphinic acid
SMILES:CCCCCCCCCCCC(O)CC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCCC1CC1CCCCCC
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent Phosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000109 mg/mLALOGPS
logP7.06ALOGPS
logP8.89ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area154.61 Å2ChemAxon
Rotatable Bond Count38ChemAxon
Refractivity195.21 m3·mol-1ChemAxon
Polarizability86.97 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
PS(14:0(3-OH)/19:0cycv8c) + Hydrogen ion > PE(14:0(3-OH)/19:0cycv8c) + Carbon dioxide
PG(18:1(9Z)/19:iso) + PE(14:0(3-OH)/19:0cycv8c) > Ethanolamine + CL(18:1(9Z)/19:0cycv8c/14:0/19:0cycv8c)
PG(18:1(9Z)/14:0(3-OH)) + PE(14:0(3-OH)/19:0cycv8c) > Ethanolamine + CL(18:1(9Z)/14:0/14:0/19:0cycv8c)
PE(14:0(3-OH)/19:0cycv8c) + PG(19:iso/15:0cyclo) > Ethanolamine + CL(19:0cycv8c/15:0cyclo/14:0/19:0cycv8c)
PE(14:0(3-OH)/19:0cycv8c) + PG(16:0/19:0cycw8c) > Ethanolamine + CL(19:0cycv8c/16:0/14:0/19:0cycv8c)
PE(14:0(3-OH)/19:0cycv8c) + PG(16:1(9Z)/14:0) > Ethanolamine + CL(19:0cycv8c/16:1(9Z)/14:0/19:0cycv8c)
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9140200200-2905aedca0325a7be0afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9130101000-86ab90e0c490a803d858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9241011000-c33056fb1ae9c3c513feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00tg-0290201200-dda113cdda1618819e95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-5690200000-d41853b8603dca9deb95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9220000000-51ce3c578ed92c723cf3View 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
  • Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-96 Pubmed: 22753057
  • 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

Protein Details
• Phosphatidylserine decarboxylase proenzyme
General function:
Involved in phosphatidylserine decarboxylase activity
Specific function:
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2)
Gene Name:
psd
Locus Tag:
PA4957
Molecular weight:
32 kDa
Reactions
Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).

Transporters

Protein Details
• Probable phospholipid ABC transporter permease protein mlaE
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
Locus Tag:
PA4455
Molecular weight:
28.4 kDa