PE-NMe(15:1(9Z)/20:0) (YMDB13983)

Identification
YMDB IDYMDB13983
NamePE-NMe(15:1(9Z)/20:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE-NMe(15:1(9Z)/20:0) 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(15:1(9Z)/20:0), in particular, consists of one 9Z-pentadecenoyl chain to the C-1 atom, and one eicosanoyl 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
SynonymsNot Available
CAS numberNot Available
WeightAverage: 746.064
Monoisotopic: 745.562155538
InChI KeyXUAANAHWBKGMCD-SQFISAMPSA-N
InChIInChI=1S/C41H80NO8P/c1-4-6-8-10-12-14-16-18-19-20-21-22-24-26-28-30-32-34-41(44)50-39(38-49-51(45,46)48-36-35-42-3)37-47-40(43)33-31-29-27-25-23-17-15-13-11-9-7-5-2/h13,15,39,42H,4-12,14,16-38H2,1-3H3,(H,45,46)/b15-13-
IUPAC Name[2-(icosanoyloxy)-3-[(9Z)-pentadec-9-enoyloxy]propoxy][2-(methylamino)ethoxy]phosphinic acid
Traditional IUPAC Name2-(icosanoyloxy)-3-[(9Z)-pentadec-9-enoyloxy]propoxy(2-(methylamino)ethoxy)phosphinic acid
Chemical FormulaC41H80NO8P
SMILES[H]C(COC(=O)CCCCCCC\C=C/CCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCCCCCCCCCCCCCC
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
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Secondary amine
  • Secondary aliphatic amine
  • 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 Solubility4.3e-05 g/LALOGPS
logP8.97ALOGPS
logP11.65ChemAxon
logS-7.2ALOGPS
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 Count42ChemAxon
Refractivity210.7 m³·mol⁻¹ChemAxon
Polarizability93.04 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(15:1(9Z)/20:0)PW002930 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PE(15:1(9Z)/20:0) + S-Adenosyl-L-methionine → PE-NMe(15:1(9Z)/20:0) + hydron + S-Adenosylhomocysteine
PE-NMe(15:1(9Z)/20:0) + S-Adenosyl-L-methionine → PE-NMe2(15:1(9Z)/20:0) + 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_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9040110100-01eed1408b8f1de21f27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9140001000-13bcccd93a49c017fddaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9170010000-719538fc3b2fd24b03ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-007c-1192201200-7184d95b06fd694cde31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fg9-6491100000-74f16cdfea29f3271922JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-5ee962c954c0e2275425JSpectraViewer
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. 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.