Record Information
Version1.0
Creation Date2016-10-03 18:09:25 UTC
Update Date2020-05-21 16:26:23 UTC
BMDB IDBMDB0010568
Secondary Accession Numbers
  • BMDB10568
Metabolite Identification
Common NamePE-NMe2(16:0/18:1(9Z))
DescriptionPE-NMe2(16:0/18:1(9Z)) is a dimethylphosphatidylethanolamine. It is a glycerophospholipid, and is formed by sequential methylation of phosphatidylethanolamine as part of a mechanism for biosynthesis of phosphatidylcholine. Dimethylphosphatidylethanolamines 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-NMe2(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl 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
Synonyms
ValueSource
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine-N,N-dimethylHMDB
DMPE(16:0/18:1(9Z))HMDB
Chemical FormulaC41H80NO8P
Average Molecular Weight746.0496
Monoisotopic Molecular Weight745.562155053
IUPAC Name[2-(dimethylamino)ethoxy][(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional Name2-(dimethylamino)ethoxy((2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C41H80NO8P/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-41(44)50-39(38-49-51(45,46)48-36-35-42(3)4)37-47-40(43)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2/h19-20,39H,5-18,21-38H2,1-4H3,(H,45,46)/b20-19-/t39-/m1/s1
InChI KeyZSVMWQMKUKDZTH-DPTAKULKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dimethylphosphatidylethanolamines. These are lipids with a structure containing a glycerol moiety linked at its terminal C3 atom to a N,N-dimethylphosphoethanolamine 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 ParentDimethylphosphatidylethanolamines
Alternative Parents
Substituents
  • Dimethylphosphatidylethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • 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 Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.82ALOGPS
logP11.33ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area111.6 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity211.39 m³·mol⁻¹ChemAxon
Polarizability91.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3100003900-7d8615065fd068d7f42aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100005100-709960db218f34954e7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-4900000000-18eabef8825efde48e9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0300000900-991cde4747473733b66bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-4490400300-04ccefb44620af1a21d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-9850100000-37c2c1ac6be9bc9708f2View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0010568
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027718
KNApSAcK IDNot Available
Chemspider ID7825968
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547018
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in phosphatidylethanolamine N-methyltransferas
Specific function:
Catalyzes the three sequential steps of the methylation pathway of phosphatidylcholine biosynthesis, the SAM-dependent methylation of phosphatidylethanolamine (PE) to phosphatidylmonomethylethanolamine (PMME), PMME to phosphatidyldimethylethanolamine (PDME), and PDME to phosphatidylcholine (PC).
Gene Name:
PEMT
Uniprot ID:
Q7YRH6
Molecular weight:
22018.0
Reactions
PE-NMe(16:0/18:1(9Z)) + S-Adenosylmethionine → PE-NMe2(16:0/18:1(9Z)) + S-Adenosylhomocysteinedetails
S-Adenosylmethionine + PE-NMe2(16:0/18:1(9Z)) → S-Adenosylhomocysteine + PC(16:0/18:1(9Z))details