Showing metabocard for PE-NMe(18:1(9Z)/18:1(9Z)) (BMDB0010565)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:09:21 UTC
Update Date2020-05-21 16:26:30 UTC
BMDB IDBMDB0010565
Secondary Accession Numbers
  • BMDB10565
Metabolite Identification
Common NamePE-NMe(18:1(9Z)/18:1(9Z))
DescriptionPE-NMe(18:1(9Z)/18:1(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(18:1(9Z)/18:1(9Z)), in particular, consists of two 9Z-octadecenoyl 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
Synonyms
ValueSource
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-methylethanolamineChEBI
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-methylethanolamine zwitterionChEBI
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine-N-methylChEBI
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine-N-monomethylHMDB
MMPE(18:1(9Z)/18:1(9Z))HMDB
1,2-DOPE-meHMDB
N-Methyl-1,2-dioleoylphosphatidylethanolamineHMDB
N-Methyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamineHMDB
Chemical FormulaC42H80NO8P
Average Molecular Weight758.0603
Monoisotopic Molecular Weight757.562155053
IUPAC Name[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy][2-(methylamino)ethoxy]phosphinic acid
Traditional Name(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy(2-(methylamino)ethoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C42H80NO8P/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43-3)51-42(45)35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h18-21,40,43H,4-17,22-39H2,1-3H3,(H,46,47)/b20-18-,21-19-/t40-/m1/s1
InChI KeyLPXFOQGBESUDAX-NLEYBKGJSA-N
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 Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
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
logP8.95ALOGPS
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
Polarizability92.11 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, Positivesplash10-0a4i-4100005900-24e92de493bfebdc29afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200027200-b26298cbf5753a3524bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5910000000-820cfdf69166f9b6c594View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-1400001900-1bf2d0cd056b3c06f448View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kdi-5943710300-0421c4df034a85c40527View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9730100000-9687bb219258fda4d1abView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0010565
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027715
KNApSAcK IDNot Available
Chemspider ID7825982
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547032
PDB IDNot Available
ChEBI ID85679
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phosphatidylethanolamine N-methyltransferase
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
S-Adenosylmethionine + PE(18:1(9Z)/18:1(9Z)) → S-Adenosylhomocysteine + PE-NMe(18:1(9Z)/18:1(9Z))details
PE-NMe(18:1(9Z)/18:1(9Z)) + S-Adenosylmethionine → PE-NMe2(18:1(9Z)/18:1(9Z)) + S-Adenosylhomocysteinedetails