ECMDB: PE(15:0/15:0) (ECMDB24106) (M2MDB006223)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (2)

Record Information

Version

2.0

Creation Date

2015-09-08 17:49:21 -0600

Update Date

2015-09-14 11:20:00 -0600

Secondary Accession Numbers

ECMDB24106

Identification

Name:

PE(15:0/15:0)

Description

PE(15:0/15:0) 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(15:0/15:0), in particular, consists of two pentadecanoyl 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:

Value	Source
Phophatidylethanolamine(30:0)	HMDB
GPEtn(30:0)	HMDB
Phophatidylethanolamine(15:0/15:0)	HMDB
GPEtn(15:0/15:0)	HMDB
PE(30:0)	HMDB
1,2-Dipentadecanoyl-rac-glycero-3-phosphoethanolamine	HMDB
PE(15:0/15:0)	Lipid Annotator

Chemical Formula:

C₃₅H₇₀NO₈P

Weight:

Average: 663.906
Monoisotopic: 663.483904733

InChI Key:

SKVKIGSFTGVBOX-MGBGTMOVSA-N

InChI:

InChI=1S/C35H70NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-34(37)41-31-33(32-43-45(39,40)42-30-29-36)44-35(38)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32,36H2,1-2H3,(H,39,40)/t33-/m1/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

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

SMILES:

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

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 (LMGP02010106 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.00014 g/L	ALOGPS
logP	7.58	ALOGPS
logP	9.56	ChemAxon
logS	-6.7	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	181.8 m³·mol⁻¹	ChemAxon
Polarizability	81.18 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(15:0cyclo/15:0cyclo/15:0cyclo/18:1(9Z))	PW001064
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/15:0cyclo/19:0cycv8c)	PW001065
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/15:0cyclo)	PW001082
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo))	PW001507
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/17:0cycw7c/15:0cyclo))	PW001527
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo))	PW001531
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/19:0cycv8c/15:0cyclo))	PW001577
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/16:1(9Z))	PW001068
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/18:1(9Z))	PW001085
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/15:0cyclo)	PW001088
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/15:0cyclo/16:1(9Z))	PW001120
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/15:0cyclo)	PW001127
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/15:0cyclo/18:1(9Z))	PW001163
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/15:0cyclo)	PW001173
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/14:0/15:0cyclo)	PW001431
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/15:0cyclo/14:0) )	PW001724
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/15:0cyclo/17:0cycw7c)	PW001440
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/15:0cyclo/18:1(9Z))	PW001441
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:1(9Z)/15:0cyclo)	PW001451
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo)	PW001460

KEGG Pathways:

Not Available

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_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0010009000-bf29f526b3dc0d75633c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0010009000-bf29f526b3dc0d75633c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-0390306000-fd0bac05e999301c30ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000019000-3f586d70d000f4c90456	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0229-0010397000-b713a42cf9979cdc673a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0010393000-52febe36836d24fa12c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000019000-27a6d8e9e665f36a6b5d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000019000-9ea22d3f36be46f12634	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0100119000-650225973346e61e9fe9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000019000-c3fe7ec191a9b8064e7b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0229-0010397000-921c36e50d223c4dc0ca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0010393000-c16f7bf68f2bba11abd4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0010009000-8e6a6ac250ece931a464	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0010009000-8e6a6ac250ece931a464	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-0390306000-a2e8b4c198b5caa82b49	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:

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	HMDB0008889
Pubchem Compound ID	9546807
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. 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

PE(15:0/15:0) (ECMDB24106) (M2MDB006223)

Structure for #<Compound:0xa5b0c408>

Enzymes

Reactions

Reactions