PE-NMe(14:0/14:0) (YMDB13860)

Identification
YMDB IDYMDB13860
NamePE-NMe(14:0/14:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE-NMe(14:0/14:0) 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(14:0/14:0), in particular, consists of two tetradecanoyl 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: 649.891
Monoisotopic: 649.468255152
InChI KeyJYWNCNMWXJZGME-UHFFFAOYSA-N
InChIInChI=1S/C34H68NO8P/c1-4-6-8-10-12-14-16-18-20-22-24-26-33(36)40-30-32(31-42-44(38,39)41-29-28-35-3)43-34(37)27-25-23-21-19-17-15-13-11-9-7-5-2/h32,35H,4-31H2,1-3H3,(H,38,39)
IUPAC Name[2,3-bis(tetradecanoyloxy)propoxy][2-(methylamino)ethoxy]phosphinic acid
Traditional IUPAC Name2,3-bis(tetradecanoyloxy)propoxy(2-(methylamino)ethoxy)phosphinic acid
Chemical FormulaC34H68NO8P
SMILES[H]C(COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCCCCCCCC
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 Solubility0.00011 g/LALOGPS
logP7.48ALOGPS
logP8.9ChemAxon
logS-6.8ALOGPS
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 Count36ChemAxon
Refractivity177.37 m³·mol⁻¹ChemAxon
Polarizability79.52 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(14:0/14:0)PW002807 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PE(14:0/14:0) + S-Adenosyl-L-methionine → PE-NMe(14:0/14:0) + hydron + S-Adenosylhomocysteine
PE-NMe(14:0/14:0) + S-Adenosyl-L-methionine → PE-NMe2(14:0/14:0) + 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_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0200019000-68e842baeece205f3f05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fi1-6971715000-407f587878191560a26dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9631000000-9a81f6c76f8a2906d08eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-4000139000-7765339b541478add2deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100181000-9a36e3d87621ba1c6eabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6930000000-cf7763efe93c2dfb1738JSpectraViewer
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 IDHMDB0112935
Pubchem Compound ID9547028
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.