ECMDB: PE(18:1(9Z)/15:0) (ECMDB24123) (M2MDB006240)

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 17:49:30 -0600

Update Date

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

Secondary Accession Numbers

ECMDB24123

Identification

Name:

PE(18:1(9Z)/15:0)

Description

PE(18:1(9Z)/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 atoms. PE(18:1(9Z)/15:0), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one pentadecanoyl 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
Phophatidylethanolamine(33:1)	HMDB
Phophatidylethanolamine(18:1/15:0)	HMDB
1-Oleoyl-2-pentadecanoyl-sn-glycero-3-phosphoethanolamine	HMDB
GPEtn(33:1)	HMDB
GPEtn(18:1/15:0)	HMDB
PE(18:1/15:0)	HMDB
PE(33:1)	HMDB
1-(9Z-Octadecenoyl)-2-pentadecanoyl-sn-glycero-3-phosphoethanolamine	HMDB
PE(18:1(9Z)/15:0)	Lipid Annotator

Chemical Formula:

C₃₈H₇₄NO₈P

Weight:

Average: 703.9698
Monoisotopic: 703.515204861

InChI Key:

WEFOBQMXZVVPCJ-UVCQAILXSA-N

InChI:

InChI=1S/C38H74NO8P/c1-3-5-7-9-11-13-15-17-18-19-21-22-24-26-28-30-37(40)44-34-36(35-46-48(42,43)45-33-32-39)47-38(41)31-29-27-25-23-20-16-14-12-10-8-6-4-2/h17-18,36H,3-16,19-35,39H2,1-2H3,(H,42,43)/b18-17-/t36-/m1/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

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

SMILES:

[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(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 (LMGP02010638 )

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	8.24	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	85.7 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/14:0/18:1(9Z))	PW001061
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:0/18:1(9Z))	PW001069
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/18:1(9Z))	PW001074
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/14:0)	PW001081
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/16:1(9Z))	PW001083
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/17:0cycw7c)	PW001084
phospholipid biosynthesis CL(15:0cyclo/16:0/15:0cyclo/18:1(9Z))	PW001098
phospholipid biosynthesis CL(15:0cyclo/16:0/18:1(9Z)/15:0cyclo)	PW001111
phospholipid biosynthesis CL(15:0cyclo/16:0/18:1(9Z)/16:0)	PW001112
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/15:0cyclo/18:1(9Z))	PW001122
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/18:1(9Z)/15:0cyclo)	PW001136
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/18:1(9Z)/16:1(9Z))	PW001137
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/17:0cycw7c/18:1(9Z))	PW001154
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/18:1(9Z)/17:0cycw7c)	PW001156
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/14:0/15:0cyclo)	PW001159
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/15:0cyclo/14:0)	PW001161
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/17:0cycw7c/17:0cycw7c)	PW001170
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/18:1(9Z)/19:0cycv8c)	PW001197
phospholipid biosynthesis CL(16:0/15:0cyclo/15:0cyclo/18:1(9Z))	PW001224
phospholipid biosynthesis CL(16:0/15:0cyclo/18:1(9Z)/15:0cyclo)	PW001239
phospholipid biosynthesis CL(16:0/15:0cyclo/18:1(9Z)/16:0)	PW001242
phospholipid biosynthesis CL(16:0/16:0/18:1(9Z)/15:0cyclo)	PW001279
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/15:0cyclo)	PW001545
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/17:0cycw7c/18:1(9Z))	PW001659
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/18:1(9Z)/17:0cycw7c)	PW001661

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_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0030000900-e74ad24759e8ea9de514	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0030000900-e74ad24759e8ea9de514	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f8f-0190300300-d7f09c754e25584ac52b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000011900-10ef1396720c799df517	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-0011691600-f0d840b05dbe3b807c19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0011691100-a8c958e2923ae245c29c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000010900-ccdad9d3ab81c96b6e8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000022900-58cb89f1ace59e110505	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0100319100-220b8097f2b3f66adb95	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0030000900-1ed6cde8dca0bdab7337	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0030000900-1ed6cde8dca0bdab7337	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f8f-0190300300-14391d25908ad3b533cd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000011900-e74d18c3f8af099fa4f9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-0011691600-d79744be2e27c543a627	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0011691100-312ff6626756cfd3a136	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	HMDB0009054
Pubchem Compound ID	52924339
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(18:1(9Z)/15:0) (ECMDB24123) (M2MDB006240)

Structure for #<Compound:0xa7f4ede8>

Enzymes

Reactions

Reactions