P. aeruginosa Metabolome Database: PE(14:0/14:0) (PAMDB000751)

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

PAMDB000751

Identification

Name:

PE(14:0/14:0)

Description:

PE(14:0/14:0) 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(14:0/14:0), in particular, consists of two tetradecanoyl 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-Dimyristoyl-rac-glycero-3-phosphoethanolamine
1,2-ditetradecanoyl-rac-glycero-3-phosphoethanolamine
1-phosphatidylethanolamine
O-(1-β-acyl-2-acyl-sn-glycero-3-phospho)-ethanolamine
A 1-phosphatidylethanolamine
A phosphatidylethenolamine
An L-1-phosphotidylethanolamine
Glycerophosphoethanolamine
GPEtn(14:0/14:0)
GPEtn(28:0)
L-1-phosphotidylethanolamine
O-(1-β-acyl-2-acyl-sn-glycero-3-phospho)-ethanolamine
PE(14:0/14:0)
PE(28:0)
Phophatidylethanolamine(14:0/14:0)
Phophatidylethanolamine(28:0)
Phosphatidylethanolamine
Phosphatidylethanolamine (ecoli)
PtdEtn

Chemical Formula:

C₃₃H₆₆NO₈P

Average Molecular Weight:

635.8528

Monoisotopic Molecular Weight:

635.452604605

InChI Key:

NEZDNQCXEZDCBI-WJOKGBTCSA-N

InChI:

InChI=1S/C33H66NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-32(35)39-29-31(30-41-43(37,38)40-28-27-34)42-33(36)26-24-22-20-18-16-14-12-10-8-6-4-2/h31H,3-30,34H2,1-2H3,(H,37,38)/t31-/m1/s1

CAS number:

Not Available

IUPAC Name:

(2-aminoethoxy)[(2R)-2,3-bis(tetradecanoyloxy)propoxy]phosphinic acid

Traditional IUPAC Name:

2-aminoethoxy((2R)-2,3-bis(tetradecanoyloxy)propoxy)phosphinic acid

SMILES:

[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC

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 (LMGP02010352 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.000205 mg/mL	ALOGPS
logP	7.06	ALOGPS
logP	8.67	ChemAxon
logS	-6.5	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	35	ChemAxon
Refractivity	172.6 m³·mol^-1	ChemAxon
Polarizability	76.48 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:

applipoprotein + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + lipoprotein
Adenosine triphosphate + Water + PE(14:0/14:0) > ADP + Hydrogen ion + Phosphate + PE(14:0/14:0)
Adenosine triphosphate + Water + PE(14:0/14:0) > ADP + Hydrogen ion + Phosphate + PE(14:0/14:0)
-->-->-->-->-->-->-->-->-->-->-->-->2 S-Adenosylmethionine + PE(14:0/14:0) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylethanolamine (dihexadec-9,10-cyclo-anoyl, N-C16:0 cyclo) +2 Hydrogen ion
2 S-Adenosylmethionine + PE(14:0/14:0) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylethanolamine (dioctadec-11,12-cyclo-anoyl, N-C18:0 cyclo) +2 Hydrogen ion
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Adenosine triphosphate + Dodecanoate (N-C12:0) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + Adenosine triphosphate + tetradecanoate (n-C14:0) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) + Adenosine triphosphate + Tetradecenoate (N-C14:1) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Adenosine triphosphate + Palmitic acid > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Adenosine triphosphate + Octadecanoate (N-C18:0) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Adenosine triphosphate + Octadecenoate (N-C18:1) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphoethanolamine KDO(2)-lipid (A)

More...

Pathways:

Glycerophospholipid metabolism pae00564
Metabolic pathways pae01100

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9120302000-8fbb8bdc68d27155acf0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9220110000-9e7c385e3e9ac321792d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9250120000-c02f43939ccb74ea4052	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ae9-1290313000-5ef301777e2a16f1bf25	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-6591200000-4a080b6320f9a7b2fc1a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9210000000-b9ee34dbfebf733936cb	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	HMDB08821
Pubchem Compound ID	9852308
Kegg ID	C00350
ChemSpider ID	8028021
Wikipedia	Lecithin
BioCyc ID	L-1-PHOSPHATIDYL-ETHANOLAMINE
EcoCyc ID	L-1-PHOSPHATIDYL-ETHANOLAMINE

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).

Protein Details

• Lipid A export ATP-binding/permease protein msbA

General function:: Involved in nucleotide binding
Specific function:: Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:: msbA
Locus Tag:: PA4997
Molecular weight:: 66.4 kDa

Protein Details

• Apolipoprotein N-acyltransferase

General function:: Involved in N-acyltransferase activity
Specific function:: Transfers the fatty acyl group on membrane lipoproteins
Gene Name:: lnt
Locus Tag:: PA3984
Molecular weight:: 56 kDa

Transporters

Protein Details

• Lipid A export ATP-binding/permease protein msbA

General function:: Involved in nucleotide binding
Specific function:: Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:: msbA
Locus Tag:: PA4997
Molecular weight:: 66.4 kDa

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(14:0/14:0) (PAMDB000751)

Structure for PE(14:0/14:0) (PAMDB000751)

Enzymes

Reactions

Transporters