ECMDB: PE(19:iso/19:iso) (ECMDB23534) (M2MDB003924)

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

Proteins (7)

Record Information

Version

2.0

Creation Date

2012-10-24 09:54:34 -0600

Update Date

2015-09-14 11:19:53 -0600

Secondary Accession Numbers

ECMDB23534

Identification

Name:

PE(19:iso/19:iso)

Description

PE(19:iso/19:iso) 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(19:iso/19:iso), in particular, consists of two 17-methylocatdecanoyl 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

Synonyms:

1,2-di17-methylocatdecanoyl-rac-glycero-3-phosphoethanolamine
1,2-di17-methylocatdecanoyl-rac-glycero-3-phosphoethanolamine
GPEtn(19:0/19:0)
GPEtn(38:0)
PE(19:0/19:0)
PE(38:0)
Phophatidylethanolamine(19:0/19:0)
Phophatidylethanolamine(38:0)

Chemical Formula:

C₄₃H₈₆NO₈P

Weight:

Average: 776.1186
Monoisotopic: 775.609105245

InChI Key:

CMXMESZEAVYGEC-VQJSHJPSSA-N

InChI:

InChI=1S/C43H86NO8P/c1-39(2)31-27-23-19-15-11-7-5-9-13-17-21-25-29-33-42(45)49-37-41(38-51-53(47,48)50-36-35-44)52-43(46)34-30-26-22-18-14-10-6-8-12-16-20-24-28-32-40(3)4/h39-41H,5-38,44H2,1-4H3,(H,47,48)/t41-/m1/s1

CAS number:

Not Available

IUPAC Name:

(2-aminoethoxy)[(2R)-2,3-bis[(17-methyloctadecanoyl)oxy]propoxy]phosphinic acid

Traditional IUPAC Name:

2-aminoethoxy((2R)-2,3-bis[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid

SMILES:

CC(C)CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCC(C)C

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

Molecular Framework

Aliphatic acyclic 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	3.9e-05 g/L	ALOGPS
logP	8.93	ALOGPS
logP	12.8	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	43	ChemAxon
Refractivity	218.51 m³·mol⁻¹	ChemAxon
Polarizability	97.33 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:

More...

SMPDB Pathways:

phospholipid biosynthesis (CL(17:0cycw7c/19:0cycv8c/14:0/19:0cycv8c))	PW001482
phospholipid biosynthesis (CL(17:0cycw7c/19:0cycv8c/17:0cycw7c/19:0cycv8c))	PW001484
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/19:0cycv8c/16:1(9Z)))	PW001317
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/19:0cycv8c/19:0cycv8c))	PW001319
phospholipid biosynthesis (CL(19:0cycv8c/17:0cycw7c/14:0/19:0cycv8c))	PW001404
phospholipid biosynthesis (CL(19:0cycv8c/17:0cycw7c/17:0cycw7c/19:0cycv8c))	PW001406
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/14:0))	PW001432
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/15:0cyclo))	PW001433
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/16:0))	PW001434
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/16:1(9Z)))	PW001435
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/18:1(9Z)))	PW001438
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/17:0cycw7c/16:0))	PW001445
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/17:0cycw7c/16:1(9Z)))	PW001446
phospholipid biosynthesis CL(15:0cyclo/16:0/19:0cycv8c/19:0cycv8c)	PW001116
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/19:0cycv8c/19:0cycv8c)	PW001141
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/16:0/19:0cycv8c)	PW001190
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/16:1(9Z)/19:0cycv8c)	PW001192
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/19:0cycv8c/16:0)	PW001200
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/19:0cycv8c/16:1(9Z))	PW001201
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/19:0cycv8c/19:0cycv8c)	PW001203
phospholipid biosynthesis CL(16:0/14:0/19:0cycv8c/19:0cycv8c)	PW001219
phospholipid biosynthesis CL(16:0/15:0cyclo/19:0cycv8c/19:0cycv8c)	PW001247
phospholipid biosynthesis CL(16:0/16:1(9Z)/19:0cycv8c/19:0cycv8c)	PW001337
phospholipid biosynthesis CL(16:0/17:0cycw7c/19:0cycv8c/19:0cycv8c)	PW001354
phospholipid biosynthesis CL(16:0/19:0cycv8c/14:0/19:0cycv8c)	PW001390
phospholipid biosynthesis CL(16:0/19:0cycv8c/16:1(9Z)/19:0cycv8c)	PW001398
phospholipid biosynthesis CL(16:0/19:0cycv8c/17:0cycw7c/19:0cycv8c)	PW001401
phospholipid biosynthesis CL(16:0/19:0cycv8c/18:1(9Z)/19:0cycv8c)	PW001409
phospholipid biosynthesis CL(16:0/19:0cycv8c/19:0cycv8c/14:0)	PW001410
phospholipid biosynthesis CL(16:0/19:0cycv8c/19:0cycv8c/16:1(9Z))	PW001411
phospholipid biosynthesis CL(16:0/19:0cycv8c/19:0cycv8c/17:0cycw7c)	PW001412
phospholipid biosynthesis CL(16:0/19:0cycv8c/19:0cycv8c/18:1(9Z))	PW001413
phospholipid biosynthesis CL(16:1(9Z)/14:0/19:0cycv8c/19:0cycv8c)	PW001430
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/19:0cycv8c/19:0cycv8c)	PW001469
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/19:0cycv8c/19:0cycv8c)	PW001557
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/19:0cycv8c/19:0cycv8c)	PW001614
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/14:0/19:0cycv8c)	PW001617
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/16:1(9Z)/19:0cycv8c)	PW001626
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/18:1(9Z)/19:0cycv8c)	PW001637
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/14:0)	PW001639
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/16:1(9Z))	PW001641
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/18:1(9Z))	PW001643

KEGG Pathways:

Glycerophospholipid metabolism ec00564

EcoCyc Pathways:

Not Available

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	splash10-0006-9020200200-314532a670a6d751a320	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9120100100-5c95c8d9392a1ba49d39	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9034101000-a48495c1899321ec568f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00ba-1190400500-daa46ba7757766d098a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-5490200100-a643c58ae79588379653	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9210000000-b018c9fb0478745feac3	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:

Casadei MA, Mañas P, Niven G, Needs E, Mackey BM. (2002) "Role of membrane fluidity in pressure resistance of Escherichia coli NCTC 8164." Appl Environ Microbiol. 68(12):5965-72. Pubmed: 12450817
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
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(19:iso/19:iso) (ECMDB23534) (M2MDB003924)

Structure for #<Compound:0xab46ca20>

Enzymes

Reactions

Reactions

Reactions

Transporters