PE-NMe(16:1(9Z)/20:1(13Z)) (YMDB13990)

Identification
YMDB IDYMDB13990
NamePE-NMe(16:1(9Z)/20:1(13Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPE-NMe(16:1(9Z)/20:1(13Z)) 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(16:1(9Z)/20:1(13Z)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 13Z-eicosenoyl 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: 758.075
Monoisotopic: 757.562155538
InChI KeyDHFHCDDOVGDUCI-RYOQUFEFSA-N
InChIInChI=1S/C42H80NO8P/c1-4-6-8-10-12-14-16-18-19-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43-3)38-48-41(44)34-32-30-28-26-24-22-17-15-13-11-9-7-5-2/h14-17,40,43H,4-13,18-39H2,1-3H3,(H,46,47)/b16-14-,17-15-
IUPAC Name{3-[(9Z)-hexadec-9-enoyloxy]-2-[(13Z)-icos-13-enoyloxy]propoxy}[2-(methylamino)ethoxy]phosphinic acid
Traditional IUPAC Name3-[(9Z)-hexadec-9-enoyloxy]-2-[(13Z)-icos-13-enoyloxy]propoxy(2-(methylamino)ethoxy)phosphinic acid
Chemical FormulaC42H80NO8P
SMILES[H]C(COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCCCCCC\C=C/CCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.1e-05 g/LALOGPS
logP8.93ALOGPS
logP11.73ChemAxon
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 Count42ChemAxon
Refractivity216.42 m³·mol⁻¹ChemAxon
Polarizability93.43 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(16:1(9Z)/20:1(13Z))PW002937 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PE(16:1(9Z)/20:1(13Z)) + S-Adenosyl-L-methionine → PE-NMe(16:1(9Z)/20:1(13Z)) + hydron + S-Adenosylhomocysteine
PE-NMe(16:1(9Z)/20:1(13Z)) + S-Adenosyl-L-methionine → PE-NMe2(16:1(9Z)/20:1(13Z)) + 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, Positivesplash10-0a4i-9040100100-fab8e41adfec0448782dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9040001000-02abc74d6111fd8f1572JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9172011000-5fa6998df2fad1aa7696JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zg0-1192201200-41b70736026d19026c06JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-5390100000-c769ccee84756cd335fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-0e09798595efb5b89e5bJSpectraViewer
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.