ECMDB: PE(14:0/18:1(9Z)) (ECMDB24104) (M2MDB006221)

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 17:49:20 -0600

Update Date

2015-09-14 11:19:59 -0600

Secondary Accession Numbers

ECMDB24104

Identification

Name:

PE(14:0/18:1(9Z))

Description

PE(14:0/18:1(9Z)) 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(14:0/18:1(9Z)), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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:

Value	Source
1-Tetradecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine	ChEBI
1-Tetradecanoyl-2-(9Z-octadecenoyl)-sn-phosphatidylethanolamine zwitterion	ChEBI
PE (14:0/18:1N-9)	ChEBI
PE(32:1)	HMDB
GPEtn(14:0/18:1)	HMDB
Phophatidylethanolamine(14:0/18:1)	HMDB
1-Myristoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine	HMDB
GPEtn(32:1)	HMDB
Phophatidylethanolamine(32:1)	HMDB
PE(14:0/18:1)	HMDB
PE(14:0/18:1(9Z))	Lipid Annotator

Chemical Formula:

C₃₇H₇₂NO₈P

Weight:

Average: 689.9432
Monoisotopic: 689.499554797

InChI Key:

QZGYPUQNTDWNBR-XHYHITGYSA-N

InChI:

InChI=1S/C37H72NO8P/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-37(40)46-35(34-45-47(41,42)44-32-31-38)33-43-36(39)29-27-25-23-21-19-14-12-10-8-6-4-2/h16-17,35H,3-15,18-34,38H2,1-2H3,(H,41,42)/b17-16-/t35-/m1/s1

CAS number:

Not Available

IUPAC Name:

(2-aminoethoxy)[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy]phosphinic acid

Traditional IUPAC Name:

2-aminoethoxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy)phosphinic acid

SMILES:

[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC

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

1,2-diacyl-sn-glycero-3-phosphoethanolamine (CHEBI:85237 )
Diacylglycerophosphoethanolamines (LMGP02011247 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	9.9e-05 g/L	ALOGPS
logP	8.01	ALOGPS
logP	10.09	ChemAxon
logS	-6.8	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	38	ChemAxon
Refractivity	192.12 m³·mol⁻¹	ChemAxon
Polarizability	83.63 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)/14:0/17:0cycw7c/14:0))	PW001498
phospholipid biosynthesis (CL(18:1(9Z)/16:0/14:0/18:1(9Z)))	PW001582
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/14:0/18:1(9Z)))	PW001608
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/14:0/18:1(9Z)))	PW001668
phospholipid biosynthesis (CL(18:1(9Z)/19:0cycv8c/14:0/18:1(9Z)))	PW001233
phospholipid biosynthesis (CL(19:0cycv8c/18:1(9Z)/14:0/18:1(9Z)))	PW001415
phospholipid biosynthesis CL(14:0/16:0/14:0/18:1(9Z))	PW001033
phospholipid biosynthesis CL(14:0/16:0/18:1(9Z)/14:0)	PW001037
phospholipid biosynthesis CL(14:0/18:1(9Z)/14:0/14:0)	PW001044
phospholipid biosynthesis CL(16:0/14:0/14:0/18:1(9Z))	PW001207
phospholipid biosynthesis CL(16:0/16:0/14:0/18:1(9Z))	PW001255
phospholipid biosynthesis CL(16:0/16:0/18:1(9Z)/14:0)	PW001266
phospholipid biosynthesis CL(16:0/18:1(9Z)/14:0/16:0)	PW001356
phospholipid biosynthesis CL(16:0/18:1(9Z)/16:0/14:0)	PW001358
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/18:1(9Z))	PW001521
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/14:0)	PW001544
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/14:0/16:1(9Z))	PW001572
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/14:0)	PW001574

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_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0030009000-a9e907e9bfd07ce2135f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0030009000-a9e907e9bfd07ce2135f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-005i-0190303000-cc54394b3ca262da6029	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000019000-a15ebcb20c9e09cf37dc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0005-0011697000-2884cd6144c3bb1aec5c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0011693000-e15f22a4f276d8bbed83	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0030009000-ed1ec79aac8617fccfda	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0030009000-ed1ec79aac8617fccfda	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-005i-0190303000-6dd7480aa09504760a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000019000-97c11016ea748a8c68d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0005-0011697000-c8c712c46be915d12b75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0011693000-e443eb3bcb9668a96fb9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000010900-d71570caf7eecd1218c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000022900-87a2cd13fd62a0ed0a6f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0101119100-6e3906429c04a1a377c8	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	84300
HMDB ID	HMDB0008828
Pubchem Compound ID	52924944
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(14:0/18:1(9Z)) (ECMDB24104) (M2MDB006221)

Structure for #<Compound:0xa7eddae4>

Enzymes

Reactions

Reactions