PE-NMe(18:0/18:1(9Z)) (YMDB13998)

Identification
YMDB IDYMDB13998
NamePE-NMe(18:0/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE-NMe(18:0/18:1(9Z)) is a monomethylphosphatidylethanolamine. It is a glycerophospholipid, and is formed by sequential methylation of phosphatidylethanolamine as part of a mechanism for biosynthesis of phosphatidylcholine. Monomethylphosphatidylethanolamines 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-NMe(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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Monomethylphosphatidylethanolamine
  • Monomethylphosphatidylethanolamine(18:0/18:1(9Z))
CAS numberNot Available
WeightAverage: 760.091
Monoisotopic: 759.577805602
InChI KeyFTQVYYIOBHBJOV-VZCXRCSSSA-N
InChIInChI=1S/C42H82NO8P/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43-3)51-42(45)35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h19,21,40,43H,4-18,20,22-39H2,1-3H3,(H,46,47)/b21-19-
IUPAC Name[2-(methylamino)ethoxy]({2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy})phosphinic acid
Traditional IUPAC Name2-(methylamino)ethoxy(2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy)phosphinic acid
Chemical FormulaC42H82NO8P
SMILES[H]C(COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCC\C=C/CCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as monomethylphosphatidylethanolamines. These are lipids with a structure containing a glycerol moiety linked at its terminal C3 atom to a N-methylphosphoethanolamine 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 ParentMonomethylphosphatidylethanolamines
Alternative Parents
Substituents
  • Monomethylphosphatidylethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary amine
  • Secondary aliphatic amine
  • 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
logP9.13ALOGPS
logP12.09ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)10.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.39 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity215.3 m³·mol⁻¹ChemAxon
Polarizability95.18 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(18:0/18:1(9Z))PW002945 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PE(18:0/18:1(9Z)) + S-Adenosyl-L-methionine → PE-NMe(18:0/18:1(9Z)) + hydron + S-Adenosylhomocysteine
PE-NMe(18:0/18:1(9Z)) + S-Adenosyl-L-methionine → PE-NMe2(18:0/18:1(9Z)) + S-Adenosylhomocysteine + hydron
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_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-1300000900-25970a1fe09af54eddb8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-5981710400-da8ab3880599521d3b88JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9630000000-1458272b04d99c31446aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4100003900-674ab4e15eb567732632JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200026300-0cfe4608cb24142d45c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6910000000-ae59a52c2324f40462ecJSpectraViewer
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 IDHMDB0112970
Pubchem Compound ID131820086
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot 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.
Protein Details
2. 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.