P. aeruginosa Metabolome Database: PE(17:0cycw7c/17:0cycw7c) (PAMDB002027)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB002027

Identification

Name:

PE(17:0cycw7c/17:0cycw7c)

Description:

PE(17:0cycw7c/17:0cycw7c) 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 positions. PE(17:0cycw7c/17:0cycw7c), in particular, consists of two heptadec-9-10-cyclo-anoyl chains at positions C-1 and C-2. 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:

1,2-diheptadec-9-10-cyclo-anoyl-rac-glycero-3-phosphoethanolamine
1,2-diheptadec-cyclopropanol-rac-glycero-3-phosphoethanolamine
1,2-diNULL-rac-glycero-3-phosphoethanolamine
GPEtn(17:0/17:0)
GPEtn(34:0)
PE(17:0/17:0)
PE(34:0)
Phophatidylethanolamine(17:0/17:0)
Phophatidylethanolamine(34:0)

Chemical Formula:

C₃₉H₇₄NO₈P

Average Molecular Weight:

715.9805

Monoisotopic Molecular Weight:

715.515204861

InChI Key:

FTCITDHJQWUTEF-GGTDZKDPSA-N

InChI:

InChI=1S/C39H74NO8P/c1-3-5-7-15-21-33-29-35(33)23-17-11-9-13-19-25-38(41)45-31-37(32-47-49(43,44)46-28-27-40)48-39(42)26-20-14-10-12-18-24-36-30-34(36)22-16-8-6-4-2/h33-37H,3-32,40H2,1-2H3,(H,43,44)/t33?,34?,35?,36?,37-/m1/s1

CAS number:

Not Available

IUPAC Name:

(2-aminoethoxy)[(2R)-2,3-bis({[8-(2-hexylcyclopropyl)octanoyl]oxy})propoxy]phosphinic acid

Traditional IUPAC Name:

2-aminoethoxy(2R)-2,3-bis({[8-(2-hexylcyclopropyl)octanoyl]oxy})propoxyphosphinic acid

SMILES:

CCCCCCC1CC1CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCC1CC1CCCCCC

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
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Organic phosphate
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Amine
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	3.83e-05 mg/mL	ALOGPS
logP	7.62	ALOGPS
logP	9.78	ChemAxon
logS	-7.3	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	37	ChemAxon
Refractivity	196.39 m³·mol^-1	ChemAxon
Polarizability	86.1 Å³	ChemAxon
Number of Rings	2	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:

More...

Pathways:

Glycerophospholipid metabolism pae00564

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9020201200-49a30196363c3bd0f714	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9121102000-a49ebfef4d3904576d11	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9024021000-3e59eb0f7538c158e46a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03ec-1190401300-0f20ad4fe0914c7763f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01sl-5490200000-cdf8f4d0474c1f3f2eca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9210000000-b1113bed31102fe3b611	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
Oursel, D., Loutelier-Bourhis, C., Orange, N., Chevalier, S., Norris, V., Lange, C. M. (2007). "Lipid composition of membranes of Escherichia coli by liquid chromatography/tandem mass spectrometry using negative electrospray ionization." Rapid Commun Mass Spectrom 21:1721-1728. Pubmed: 17477452
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	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not 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

PE(17:0cycw7c/17:0cycw7c) (PAMDB002027)

Structure for PE(17:0cycw7c/17:0cycw7c) (PAMDB002027)

Enzymes

Reactions

Transporters