PE-NMe2(18:2(9Z,11Z)/18:2(9Z,11Z)) (YMDB15901)

Identification
YMDB IDYMDB15901
NamePE-NMe2(18:2(9Z,11Z)/18:2(9Z,11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE-NMe2(18:2(9Z,11Z)/18:2(9Z,11Z)) 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(18:2(9Z,11Z)/18:2(9Z,11Z)), in particular, consists of two 9Z,11Z-octadecadienoyl chain at positions C-1 and C2. 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
SynonymsNot Available
CAS numberNot Available
WeightAverage: 768.07
Monoisotopic: 767.546505474
InChI KeyUBIMFCUYOQPLLD-TWGXYJQZSA-N
InChIInChI=1S/C43H78NO8P/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/h15-22,41H,5-14,23-40H2,1-4H3,(H,47,48)/b17-15-,18-16-,21-19-,22-20-
IUPAC Name{2,3-bis[(9Z,11Z)-octadeca-9,11-dienoyloxy]propoxy}[2-(dimethylamino)ethoxy]phosphinic acid
Traditional IUPAC Name2,3-bis[(9Z,11Z)-octadeca-9,11-dienoyloxy]propoxy(2-(dimethylamino)ethoxy)phosphinic acid
Chemical FormulaC43H78NO8P
SMILES[H]C(COC(=O)CCCCCCC\C=C/C=C\CCCCCC)(COP(O)(=O)OCCN(C)C)OC(=O)CCCCCCC\C=C/C=C\CCCCCC
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
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • 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 Solubility4.8e-05 g/LALOGPS
logP8.81ALOGPS
logP11.13ChemAxon
logS-7.2ALOGPS
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 Count40ChemAxon
Refractivity223.94 m³·mol⁻¹ChemAxon
Polarizability94.58 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
Lysolipid incorporation into ER PC(18:2(9Z,11Z)/18:2(9Z,11Z))PW002789 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(18:2(9Z,11Z)/18:2(9Z,11Z))PW002797 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PE-NMe(18:2(9Z,11Z)/18:2(9Z,11Z)) + S-Adenosyl-L-methionine → PE-NMe2(18:2(9Z,11Z)/18:2(9Z,11Z)) + S-Adenosylhomocysteine + hydron
PE-NMe2(18:2(9Z,11Z)/18:2(9Z,11Z)) + S-Adenosyl-L-methionine → S-Adenosylhomocysteine + hydron + PC(18:2(9Z,11Z)/18:2(9Z,11Z))
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, Positivesplash10-00di-9020210100-58a94a840c5310e19746JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9021001000-8ac1b291a6f061b5c9d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9034022000-48f9bc5792b95b2b6c4dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02di-1190211200-eb1a59f73e36d8e68ba8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5390100000-1e1037c5ec42a47405e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-5e3b205d65a13c7d033dJSpectraViewer
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 IDNot Available
Pubchem Compound IDNot Available
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.