PE-NMe2(18:1(11Z)/18:1(9Z)) (YMDB13834)

Identification
YMDB IDYMDB13834
NamePE-NMe2(18:1(11Z)/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE-NMe2(18:1(11Z)/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(18:1(11Z)/18:1(9Z)), in particular, consists of one 11Z-octadecenoyl 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Dimethylphosphatidylethanolamine
  • Dimethylphosphatidylethanolamine(18:1(11Z)/18:1(9Z))
CAS numberNot Available
WeightAverage: 772.102
Monoisotopic: 771.577805602
InChI KeyVEFZTXSCGJZAKO-FGIXQLCWSA-N
InChIInChI=1S/C43H82NO8P/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/h15,17,20,22,41H,5-14,16,18-19,21,23-40H2,1-4H3,(H,47,48)/b17-15-,22-20-
IUPAC Name[2-(dimethylamino)ethoxy]({3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy})phosphinic acid
Traditional IUPAC Name2-(dimethylamino)ethoxy(3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
Chemical FormulaC43H82NO8P
SMILES[H]C(COC(=O)CCCCCCCCC\C=C/CCCCCC)(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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentDimethylphosphatidylethanolamines
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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.0e-05 g/LALOGPS
logP9.05ALOGPS
logP11.85ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area111.6 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity221.71 m³·mol⁻¹ChemAxon
Polarizability95.35 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Mitochondria
Organoleptic PropertiesNot Available
SMPDB Pathways
Phosphatidylcholine biosynthesis PC(18:1(11Z)/18:1(9Z))PW002943 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PE-NMe(18:1(11Z)/18:1(9Z)) + S-Adenosyl-L-methionine → PE-NMe2(18:1(11Z)/18:1(9Z)) + S-Adenosylhomocysteine + hydron
PE-NMe2(18:1(11Z)/18:1(9Z)) + S-Adenosyl-L-methionine → S-Adenosylhomocysteine + hydron + PC(18:1(11Z)/18:1(9Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0300000900-d5a55a9f88eaec37ce17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05wv-7894840500-a973d9c3ea8a4ddc4065JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00pi-9850210000-affb3cdfca9a491c610bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-4200005900-bda3d6277a99bdf5c0fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100005200-3386ff6f7ca5e476b759JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5910000000-53f207c49ffb389d139eJSpectraViewer
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:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0113869
Pubchem Compound ID131820980
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot 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.