Showing metabocard for PE(16:0/16:0) (BMDB0008923)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:32:08 UTC
Update Date2020-05-21 16:28:41 UTC
BMDB IDBMDB0008923
Secondary Accession Numbers
  • BMDB08923
Metabolite Identification
Common NamePE(16:0/16:0)
DescriptionPE(16:0/16:0), also known as pe(16:0/16:0) or PE(32:0), belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages. Thus, PE(16:0/16:0) is considered to be a glycerophosphoethanolamine lipid molecule. PE(16:0/16:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(16:0/16:0) exists in all living species, ranging from bacteria to humans. PE(16:0/16:0) participates in a number of enzymatic reactions, within cattle. In particular, Cytidine monophosphate and PE(16:0/16:0) can be biosynthesized from CDP-ethanolamine and DG(16:0/16:0/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In addition, PE(16:0/16:0) can be biosynthesized from PS(16:0/16:0) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PE(16:0/16:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:0/16:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Dihexadecanoyl-sn-glycero-3-phosphoethanolamineChEBI
1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
2-Ammonioethyl (2R)-2,3-bis(palmitoyloxy)propyl phosphateChEBI
2-Ammonioethyl (2R)-2,3-bis(palmitoyloxy)propyl phosphoric acidGenerator
1,2-Dipalmitoyl-rac-glycerophosphoethanolamineHMDB
DHPEHMDB
DPPEHMDB
1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamineHMDB
1,2-Dipalmitoyl-3-phosphatidylethanolamineHMDB
1,2-Dipalmitoyl-3-phosphatidylethanolamine, (+-)-isomerHMDB
1,2-Dipalmitoyl-3-phosphatidylethanolamine, ion(1-)HMDB
Dipalmitoyl cephalinHMDB
Phosphatidylethanolamine dipalmitoateHMDB
1,2-Dipalmitoyl-3-phosphatidylethanolamine, (R)-isomerHMDB
Dipalmitoyl phosphatidylethanolamineHMDB
PE(32:0)HMDB
Phophatidylethanolamine(16:0/16:0)HMDB
1,2-Dipalmitoyl-rac-glycero-3-phosphoethanolamineHMDB
GPEtn(32:0)HMDB
Phophatidylethanolamine(32:0)HMDB
1,2-Dihexadecanoyl-rac-glycero-3-phosphoethanolamineHMDB
GPEtn(16:0/16:0)HMDB
1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(16:0/16:0)Lipid Annotator
1,2-Dipalmitoyl-glycero-3-phosphoethanolamineHMDB
Chemical FormulaC37H74NO8P
Average Molecular Weight691.972
Monoisotopic Molecular Weight691.515205345
IUPAC Name(2-aminoethoxy)[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphinic acid
Traditional NameDPPE
CAS Registry Number923-61-5
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C37H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35H,3-34,38H2,1-2H3,(H,41,42)/t35-/m1/s1
InChI KeySLKDGVPOSSLUAI-PGUFJCEWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentPhosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • 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
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Primary amine
  • 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
logP8.08ALOGPS
logP10.45ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity191 m³·mol⁻¹ChemAxon
Polarizability85.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-Ion Trap , Negativesplash10-0a4i-0090100000-78393dc4e019ebd83091View in MoNA
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0udi-0000090000-069925af450b3d115abbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-0udi-0000092000-56ad77c14f3dd6abfc2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-0006-0000029000-27be419812bef5a711b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 26V, positivesplash10-0udi-0000091000-bcc33889face46932592View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-0udi-0000090000-c5fc59cd33b54d2b0ca9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 48V, positivesplash10-0udi-0000090000-705a17812444ed5b05d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0010009000-a6e178ef3224d9865bffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0010009000-a6e178ef3224d9865bffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-0390306000-ad2b7adbfe5f6633b9d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000019000-814aefc198261f6d39f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0001397000-5c50d43804f2de04b695View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0001393000-fa8208f710210c1fb8b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000010900-bb7978dcbee6464346dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0000022900-6efdc1241c22750b2501View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0100119100-d1161af391f6b033c241View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0010009000-0eb6e92cae6cb86893c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0010009000-0eb6e92cae6cb86893c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-0390306000-ed49698119adb877ef12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000019000-9ed53d8418cab57ddd34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0001397000-861b87a9fc2981fd8bdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0001393000-5efc530efdb379be340dView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008923
DrugBank IDDB01728
Phenol Explorer Compound IDNot Available
FooDB IDFDB026113
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound445468
PDB IDPEF
ChEBI ID73005
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Ethanolaminephosphotransferase 1
General function:
Involved in ethanolaminephosphotransferase activity
Specific function:
Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the foramtion of phosphatidylethanolamine via 'Kennedy' pathway (By similarity).
Gene Name:
SELENOI
Uniprot ID:
Q17QM4
Molecular weight:
45214.0
Reactions
CDP-Ethanolamine + DG(16:0/16:0/0:0) → Cytidine monophosphate + PE(16:0/16:0)details
Enzyme Details
2. 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(16:0/16:0) → S-Adenosylhomocysteine + PE-NMe(16:0/16:0)details
PE(16:0/16:0) → PC(16:0/16:0)details
Enzyme Details
3. Cytosolic phospholipase A2
General function:
Involved in calcium ion binding
Specific function:
Has primarily calcium-dependent phospholipase and lysophospholipase activities, with a major role in membrane lipid remodeling and biosynthesis of lipid mediators of the inflammatory response (By similarity). Plays an important role in embryo implantation and parturition through its ability to trigger prostanoid production (By similarity). Preferentially hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity). Selectively hydrolyzes sn-2 arachidonoyl group from membrane phospholipids, providing the precursor for eicosanoid biosynthesis via the cyclooxygenase pathway. In an alternative pathway of eicosanoid biosynthesis, hydrolyzes sn-2 fatty acyl chain of eicosanoid lysophopholipids to release free bioactive eicosanoids. Hydrolyzes the ester bond of the fatty acyl group attached at sn-1 position of phospholipids (phospholipase A1 activity) only if an ether linkage rather than an ester linkage is present at the sn-2 position. This hydrolysis is not stereospecific. Has calcium-independent phospholipase A2 and lysophospholipase activities in the presence of phosphoinositides. Has O-acyltransferase activity. Catalyzes the transfer of fatty acyl chains from phospholipids to a primary hydroxyl group of glycerol (sn-1 or sn-3), potentially contributing to monoacylglycerol synthesis (By similarity).
Gene Name:
PLA2G4A
Uniprot ID:
A4IFJ5
Molecular weight:
85350.0
Reactions
PE(16:0/16:0) → LysoPE(16:0/0:0)details
Enzyme Details
4. Phospholipase D2
General function:
Lipid transport and metabolism
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis.
Gene Name:
PLD2
Uniprot ID:
Q0V8L6
Molecular weight:
105766.0
Reactions
PA(16:0/16:0) → PE(16:0/16:0)details