ECMDB: PE(16:1(9Z)/17:0) (ECMDB21065) (M2MDB001481)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)Transporters (3)XML

Proteins (7)

Record Information

Version

2.0

Creation Date

2012-05-31 14:57:03 -0600

Update Date

2015-09-14 11:19:24 -0600

Secondary Accession Numbers

ECMDB21065

Identification

Name:

PE(16:1(9Z)/17:0)

Description

PE(16:1(9Z)/17:0) 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 atoms. PE(16:1(9Z)/17:0), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one heptadecanoyl 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

Synonyms:

1-(9Z-hexadecenoyl)-2-heptadecanoyl-glycero-3-phosphoethanolamine
1-(9Z-hexadecenoyl)-2-margaroyl-sn-glycero-3-phosphoethanolamine
1-palmitoleoyl-2-heptadecanoyl-sn-glycero-3-phosphoethanolamine
GPEtn(16:1/17:0)
GPEtn(33:1)
PE(16:1/17:0)
PE(33:1)
Phophatidylethanolamine(16:1/17:0)
Phophatidylethanolamine(33:1)

Chemical Formula:

C₃₈H₇₄NO₈P

Weight:

Average: 703.9698
Monoisotopic: 703.515204861

InChI Key:

WSLONBAGRNPTKG-ZYODFBQNSA-N

InChI:

InChI=1S/C38H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-38(41)47-36(35-46-48(42,43)45-33-32-39)34-44-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h14,16,36H,3-13,15,17-35,39H2,1-2H3,(H,42,43)/b16-14-/t36-/m1/s1

CAS number:

Not Available

IUPAC Name:

(2-aminoethoxy)[(2R)-2-(heptadecanoyloxy)-3-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid

Traditional IUPAC Name:

2-aminoethoxy((2R)-2-(heptadecanoyloxy)-3-[(9Z)-hexadec-9-enoyloxy]propoxy)phosphinic acid

SMILES:

[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCC

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.

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
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organic nitrogen compound
Primary amine
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoethanolamines (LMGP02010521 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	8.3e-05 g/L	ALOGPS
logP	8.23	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	85.44 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:

SMPDB Pathways:

phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/16:1(9Z)/17:0cycw7c))	PW001610
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/17:0cycw7c/18:1(9Z)))	PW001619
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/16:1(9Z)))	PW001673
phospholipid biosynthesis CL(16:0/16:0/16:1(9Z)/17:0cycw7c)	PW001267
phospholipid biosynthesis CL(16:0/16:0/17:0cycw7c/16:1(9Z))	PW001273
phospholipid biosynthesis CL(16:0/16:1(9Z)/16:0/17:0cycw7c)	PW001303
phospholipid biosynthesis CL(16:0/16:1(9Z)/17:0cycw7c/16:0)	PW001315
phospholipid biosynthesis CL(16:1(9Z)/16:0/16:0/17:0cycw7c)	PW001478
phospholipid biosynthesis CL(16:1(9Z)/16:0/17:0cycw7c/16:0)	PW001491
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/17:0cycw7c)	PW001524
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/17:0cycw7c/16:1(9Z))	PW001538
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/18:1(9Z)/18:1(9Z))	PW001568
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/17:0cycw7c/18:1(9Z))	PW001592
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/17:0cycw7c)	PW001603

KEGG Pathways:

Glycerophospholipid metabolism ec00564

EcoCyc Pathways:

phospholipid biosynthesis I PHOSLIPSYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9040200100-2f7661965268b50f6058	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9140001000-42ae2f327c8e4b632605	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9162010000-419d4e7c39c1b7159e23	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0190201100-f1233930dc1f13c7672b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ug3-4390100000-73477f20b77c91b270a9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9220000000-303cd1028bfb168bf1c1	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Ames, G. F. (1968). "Lipids of Salmonella typhimurium and Escherichia coli: structure and metabolism." J Bacteriol 95:833-843. Pubmed: 4868364
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	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

1. Phosphatidylserine decarboxylase proenzyme

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).

Protein Details

2. Bifunctional protein aas

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].

Protein Details

3. Protein crcA

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

Protein Details

4. Cardiolipin synthase C

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

Protein Details

1. Probable phospholipid ABC transporter-binding protein mlaB

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

Protein Details

2. Probable phospholipid ABC transporter-binding protein mlaD

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

Protein Details

3. 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
Uniprot ID:: P64606
Molecular weight:: 27863

PE(16:1(9Z)/17:0) (ECMDB21065) (M2MDB001481)

Structure for #<Compound:0xa371cc00>

Enzymes

Reactions

Reactions

Reactions

Transporters