P. aeruginosa Metabolome Database: PE(15:0/18:1(9Z)) (PAMDB006226)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB006226

Identification

Name:

PE(15:0/18:1(9Z))

Description:

PE(15:0/18:1(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(15:0/18:1(9Z)), in particular, consists of one pentadecanoyl 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

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Not Available

Chemical Formula:

C₃₈H₇₄NO₈P

Average Molecular Weight:

703.9698

Monoisotopic Molecular Weight:

703.515204861

InChI Key:

ADCNXGARWPJRBV-UVCQAILXSA-N

InChI:

InChI=1S/C38H74NO8P/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-38(41)47-36(35-46-48(42,43)45-33-32-39)34-44-37(40)30-28-26-24-22-20-16-14-12-10-8-6-4-2/h17-18,36H,3-16,19-35,39H2,1-2H3,(H,42,43)/b18-17-/t36-/m1/s1

CAS number:

Not Available

IUPAC Name:

(2-aminoethoxy)[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy]phosphinic acid

Traditional IUPAC Name:

2-aminoethoxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy)phosphinic acid

SMILES:

[H][C@@](COC(=O)CCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC

Chemical Taxonomy

Taxonomy Description

This 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 Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

Phosphatidylethanolamines

Alternative Parents

Substituents

Diacylglycero-3-phosphoethanolamine
Phosphoethanolamine
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoethanolamines (LMGP02010458 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	8.31e-05 mg/mL	ALOGPS
logP	8.24	ALOGPS
logP	10.53	ChemAxon
logS	-6.9	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 Å²	ChemAxon
Rotatable Bond Count	39	ChemAxon
Refractivity	196.72 m³·mol^-1	ChemAxon
Polarizability	85.81 Å³	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:

PE(15:0/18:1(9Z)) + PG(19:iso/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/19:0cycv8c/18:1(9Z))
PE(15:0/18:1(9Z)) + PG(19:0cycv8c/19:iso) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/19:0cycv8c/19:0cycv8c)
PG(17:0/17:0) + PE(15:0/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/17:0cycw7c/17:0cycw7c)
PE(15:0/18:1(9Z)) + PG(14:0(3-OH)/18:1(9Z)) + PE(18:1(9Z)/15:0cyclo) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/14:0/18:1(9Z))
PG(19:0cycv8c/19:iso) + PE(15:0/18:1(9Z)) > Ethanolamine + CL(15:0cyclo/18:1(9Z)/19:0cycv8c/19:0cycv8c)
PE(15:0/18:1(9Z)) + PG(15:0/16:1) > CL(15:0cyclo/15:0cyclo/18:1(9Z)/16:0) + Ethanolamine

More...

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9140200100-a8d520f5bd75c3cf7a40	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9240001000-31c503d05ade0b9f681f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9280011000-03a37dcbd8fd26dc4852	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dl-0190201100-b784eb29ef5ff74a5bab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-5490100000-3b18dd925c2393b40fbe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9220000000-9cad625f6975a362f3c2	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	HMDB08894
Pubchem Compound ID	52924162
Kegg ID	C00350
ChemSpider ID	24768397
Wikipedia ID	Not Available
BioCyc ID	Not Available

PE(15:0/18:1(9Z)) (PAMDB006226)

Structure for PE(15:0/18:1(9Z)) (PAMDB006226)