PE-NMe(15:0/16:1(9Z)) (YMDB13913)

Identification
YMDB IDYMDB13913
NamePE-NMe(15:0/16:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE-NMe(15:0/16:1(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(15:0/16:1(9Z)), in particular, consists of one pentadecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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(15:0/16:1(9Z))
CAS numberNot Available
WeightAverage: 689.956
Monoisotopic: 689.49955528
InChI KeyJADURDCKRVMCGD-PEZBUJJGSA-N
InChIInChI=1S/C37H72NO8P/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-37(40)46-35(34-45-47(41,42)44-32-31-38-3)33-43-36(39)29-27-25-23-21-19-17-15-13-11-9-7-5-2/h14,16,35,38H,4-13,15,17-34H2,1-3H3,(H,41,42)/b16-14-
IUPAC Name{2-[(9Z)-hexadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy}[2-(methylamino)ethoxy]phosphinic acid
Traditional IUPAC Name2-[(9Z)-hexadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy(2-(methylamino)ethoxy)phosphinic acid
Chemical FormulaC37H72NO8P
SMILES[H]C(COC(=O)CCCCCCCCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCC\C=C/CCCCCC
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 Solubility6.9e-05 g/LALOGPS
logP8.16ALOGPS
logP9.87ChemAxon
logS-7ALOGPS
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 Count38ChemAxon
Refractivity192.29 m³·mol⁻¹ChemAxon
Polarizability84.48 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(15:0/16:1(9Z))PW002860 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PE(15:0/16:1(9Z)) + S-Adenosyl-L-methionine → PE-NMe(15:0/16:1(9Z)) + hydron + S-Adenosylhomocysteine
PE-NMe(15:0/16:1(9Z)) + S-Adenosyl-L-methionine → PE-NMe2(15:0/16:1(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, Positivesplash10-0006-3000029000-13a4502c7f09a4a1e5c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9100064000-85b6abd3177d01c7f47bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6920000000-40517de298a1e0be7326JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f79-1300009000-eeb368e57214b126ec4bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugu-5890504000-8e053af3afe91a878403JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9630000000-2335f3ffd1ec3f09337aJSpectraViewer
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 IDHMDB0112945
Pubchem Compound ID131820061
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.