PE-NMe2(18:0/18:1(9Z)) (YMDB13836)

Identification

YMDB ID

YMDB13836

Name

PE-NMe2(18:0/18:1(9Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PE-NMe2(18:0/18:1(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(18:0/18:1(9Z)), in particular, consists of one octadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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

Dimethylphosphatidylethanolamine
Dimethylphosphatidylethanolamine(18:0/18:1(9Z))

CAS number

Not Available

Weight

Average: 774.118
Monoisotopic: 773.593455667

InChI Key

JPXWWRACEORTKX-XDOYNYLZSA-N

InChI

InChI=1S/C43H84NO8P/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-42(45)49-39-41(40-51-53(47,48)50-38-37-44(3)4)52-43(46)36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-2/h20,22,41H,5-19,21,23-40H2,1-4H3,(H,47,48)/b22-20-

IUPAC Name

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

Traditional IUPAC Name

2-(dimethylamino)ethoxy(2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy)phosphinic acid

Chemical Formula

C₄₃H₈₄NO₈P

SMILES

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dimethylphosphatidylethanolamines. These are lipids with a structure containing a glycerol moiety linked at its terminal C3 atom to a N,N-dimethylphosphoethanolamine group, and at its C1 and C2 terminal atoms by an acyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

Dimethylphosphatidylethanolamines

Alternative Parents

Substituents

Dimethylphosphatidylethanolamine
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	9.16	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	97.01 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(18:0/18:1(9Z))

PW002945

KEGG Pathways

Not Available

SMPDB Reactions

PE-NMe(18:0/18:1(9Z)) + S-Adenosyl-L-methionine → PE-NMe2(18:0/18:1(9Z)) + S-Adenosylhomocysteine + hydron

PE-NMe2(18:0/18:1(9Z)) + S-Adenosyl-L-methionine → S-Adenosylhomocysteine + hydron + PC(18:0/18:1(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	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-3100003900-d8a6d76a8f7cbc90bbb6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9200004300-7356e89dc1c629b00466	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-4900000000-6cad0097d1e2a3e32278	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0300000900-45657c4ef218875f490a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00sl-4491510300-41f3f14972fadb55e32a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-9850210000-7e378874769b548b190d	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	HMDB0113871
Pubchem Compound ID	131820982
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:0xae57f25c>

Enzymes

Reactions