PE(15:1(11Z)/16:1(11Z)) (YMDB14069)

Identification

YMDB ID

YMDB14069

Name

PE(15:1(11Z)/16:1(11Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PE(15:1(11Z)/16:1(11Z)) 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(15:1(11Z)/16:1(11Z)), in particular, consists of one 11Z-pentadecenoyl chain to the C-1 atom, and one 11Z-hexadecenoyl 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

Not Available

CAS number

Not Available

Weight

Average: 673.913
Monoisotopic: 673.468255152

InChI Key

RHQRHFXWGZROLX-LOEBJBPCSA-N

InChI

InChI=1S/C36H68NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)45-34(33-44-46(40,41)43-31-30-37)32-42-35(38)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h8-11,34H,3-7,12-33,37H2,1-2H3,(H,40,41)/b10-8-,11-9-/t34-/m1/s1

IUPAC Name

(2-aminoethoxy)[(2R)-2-[(11Z)-hexadec-11-enoyloxy]-3-[(11Z)-pentadec-11-enoyloxy]propoxy]phosphinic acid

Traditional IUPAC Name

2-aminoethoxy((2R)-2-[(11Z)-hexadec-11-enoyloxy]-3-[(11Z)-pentadec-11-enoyloxy]propoxy)phosphinic acid

Chemical Formula

C₃₆H₆₈NO₈P

SMILES

[H][C@@](COC(=O)CCCCCCCCC\C=C/CCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCC\C=C/CCCC

Chemical Taxonomy

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.00012 g/L	ALOGPS
logP	7.63	ALOGPS
logP	9.28	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	36	ChemAxon
Refractivity	188.64 m³·mol⁻¹	ChemAxon
Polarizability	80.06 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

Endoplasmic reticulum
Mitochondria

Organoleptic Properties

Not Available

SMPDB Pathways

Phosphatidylcholine biosynthesis PC(15:1(11Z)/16:1(11Z))

PW002858

KEGG Pathways

Not Available

SMPDB Reactions

PE(15:1(11Z)/16:1(11Z)) + S-Adenosyl-L-methionine → PE-NMe(15:1(11Z)/16:1(11Z)) + hydron + S-Adenosylhomocysteine

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000090000-5185eeb11394f4fce610	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350

Synthesis Reference:

Not Available

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
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Phosphatidylethanolamine N-methyltransferase

General function:: Involved in phosphatidylethanolamine N-methyltransferas
Specific function:: S-adenosyl-L-methionine + phosphatidylethanolamine = S-adenosyl-L-homocysteine + phosphatidyl-N-methylethanolamine
Gene Name:: PEM1
Uniprot ID:: P05374
Molecular weight:: 101203.0

Reactions

S-adenosyl-L-methionine + phosphatidylethanolamine → S-adenosyl-L-homocysteine + phosphatidyl-N-methylethanolamine.

Structure for #<Compound:0x9e590f80>

Enzymes

Reactions