PE-NMe2(14:0/22:1(9Z)) (YMDB13843)

Identification

YMDB ID

YMDB13843

Name

PE-NMe2(14:0/22:1(9Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PE-NMe2(14:0/22:1(9Z)) is a dimethylphosphatidylethanolamine. It is a glycerophospholipid, and is formed by sequential methylation of phosphatidylethanolamine as part of a mechanism for biosynthesis of phosphatidylcholine. Dimethylphosphatidylethanolamines are usually found at trace levels in animal or plant tissues. They can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions.PE-NMe2(14:0/22:1(9Z)), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one 9Z-docosenoyl to the C-2 atom. Fatty acids containing 16, 18 and 20 carbons are the most common. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

CAS number

Not Available

Weight

Average: 774.118
Monoisotopic: 773.593455667

InChI Key

JXWWIGYNZUELKL-FCQUAONHSA-N

InChI

InChI=1S/C43H84NO8P/c1-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-43(46)52-41(40-51-53(47,48)50-38-37-44(3)4)39-49-42(45)35-33-31-29-27-25-16-14-12-10-8-6-2/h22-23,41H,5-21,24-40H2,1-4H3,(H,47,48)/b23-22-

IUPAC Name

[2-(dimethylamino)ethoxy]({2-[(9Z)-docos-9-enoyloxy]-3-(tetradecanoyloxy)propoxy})phosphinic acid

Traditional IUPAC Name

2-(dimethylamino)ethoxy(2-[(9Z)-docos-9-enoyloxy]-3-(tetradecanoyloxy)propoxy)phosphinic acid

Chemical Formula

C₄₃H₈₄NO₈P

SMILES

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

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	4.2e-05 g/L	ALOGPS
logP	9.17	ALOGPS
logP	12.21	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.6 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	220.59 m³·mol⁻¹	ChemAxon
Polarizability	96.84 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(14:0/22:1(9Z))

PW002952

KEGG Pathways

Not Available

SMPDB Reactions

PE-NMe(14:0/22:1(9Z)) + S-Adenosyl-L-methionine → PE-NMe2(14:0/22:1(9Z)) + S-Adenosylhomocysteine + hydron

PE-NMe2(14:0/22:1(9Z)) + S-Adenosyl-L-methionine → S-Adenosylhomocysteine + hydron + PC(14:0/22:1(9Z))

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_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9022100100-9a47e02fe8923032e6ee	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9122001000-60d61c8f0d51a9d4c75f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9252011100-ff6e9fd94a3ed84fe189	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0kki-1294200300-e56ee4a94939cab5532c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-6491100000-dc9aff74cde24fedb783	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-9111000000-42c25b71e2179a045bb4	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. Methylene-fatty-acyl-phospholipid synthase

General function:: Involved in N-methyltransferase activity
Specific function:: S-adenosyl-L-methionine + phospholipid olefinic fatty acid = S-adenosyl-L-homocysteine + phospholipid methylene fatty acid
Gene Name:: OPI3
Uniprot ID:: P05375
Molecular weight:: 23150.09961

Reactions

S-adenosyl-L-methionine + phospholipid olefinic fatty acid → S-adenosyl-L-homocysteine + phospholipid methylene fatty acid.

Structure for #<Compound:0xaa442564>

Enzymes

Reactions