Showing metabocard for PE(18:1(9Z)/18:1(9Z)) (BMDB0009059)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:34:55 UTC
Update Date2020-05-21 16:28:15 UTC
BMDB IDBMDB0009059
Secondary Accession Numbers
  • BMDB09059
Metabolite Identification
Common NamePE(18:1(9Z)/18:1(9Z))
DescriptionPE(18:1(9Z)/18:1(9Z)), also known as Pe(18:1(9z)/18:1(9z)) or pe(18:1(9z)/18:1(9z)), 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(18:1(9Z)/18:1(9Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(18:1(9Z)/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(18:1(9Z)/18:1(9Z)) exists in all living species, ranging from bacteria to humans. PE(18:1(9Z)/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(18:1(9Z)/18:1(9Z)) can be biosynthesized from PS(18:1(9Z)/18:1(9Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(18:1(9Z)/18:1(9Z)) can be biosynthesized from CDP-ethanolamine and DG(18:1(9Z)/18:1(9Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(18:1(9Z)/18:1(9Z)) can be biosynthesized from CDP-ethanolamine and DG(18:1(9Z)/18:1(9Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PE(18:1(9Z)/18:1(9Z)) can be biosynthesized from PS(18:1(9Z)/18:1(9Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PE(18:1(9Z)/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:1(9Z)/18:1(9Z)) pathway and phosphatidylcholine biosynthesis PC(18:1(9Z)/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineChEBI
1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylethanolamine zwitterionChEBI
1,2-DioleoylphosphatidylethanolamineHMDB
1,2-DOPEHMDB
1,2-DielaidoylphosphatidylethanolamineHMDB
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamineHMDB
1-2-DOPEHMDB
LipofectinHMDB
Dioleoyl cephalinHMDB
1,2-Dioleoylglycero-3-phosphoethanolamineHMDB
1-2-Di-(9-octadecenoyl)-sn-glycero-3-phosphoethethanolamineHMDB
1,2-Dioleoyl-rac-glycero-3-phosphoethanolamineHMDB
PE(18:1/18:1)HMDB
GPEtn(18:1/18:1)HMDB
Phophatidylethanolamine(36:2)HMDB
Phophatidylethanolamine(18:1/18:1)HMDB
GPEtn(36:2)HMDB
1,2-Di(9Z-octadecenoyl)-rac-glycero-3-phosphoethanolamineHMDB
PE(36:2)HMDB
PE(18:1(9Z)/18:1(9Z))Lipid Annotator
Chemical FormulaC41H78NO8P
Average Molecular Weight744.048
Monoisotopic Molecular Weight743.546505474
IUPAC Name(2-aminoethoxy)[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional Name1,2-dioleoyl-sn-gl
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C41H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,39H,3-16,21-38,42H2,1-2H3,(H,45,46)/b19-17-,20-18-/t39-/m1/s1
InChI KeyMWRBNPKJOOWZPW-NYVOMTAGSA-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
logP8.81ALOGPS
logP11.51ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity211.64 m³·mol⁻¹ChemAxon
Polarizability90.54 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 (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-001l-0090100400-2e505f9bbb1be20750d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 2V, positivesplash10-0006-0000001900-5c8d87e0015e6e5d1cb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0006-0000003900-f9393f34f408d3df66f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 6V, positivesplash10-0f6x-0000005900-0c0762234af9b7f2c3b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 8V, positivesplash10-0f6x-0001007900-cadb26b1db0ca86589e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 14V, positivesplash10-0udi-0101009200-7fcb84a56ede0e704634View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 16V, positivesplash10-0udi-0001009100-5aeac3a5eb6fed78d9a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-0udi-0000009200-86abb6550ab0e0c580fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0006-0000002900-af4784d2becf4f36e733View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-0udi-0000009200-240a0652b33b213f4a7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 43V, positivesplash10-0udi-0000009000-fcccd79c5013049d21a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 55V, positivesplash10-0udi-1111009000-a46540873bbf27bb32fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 65V, positivesplash10-0uxs-9831005000-b52b90c60bc5216ef312View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 77V, positivesplash10-015a-9600000000-d5b92aa6c5d21aff830aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 87V, positivesplash10-00ls-9500000000-aa5703b09a2b4982f7e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 99V, positivesplash10-015a-9300000000-c887c51891d1740cd6f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 110V, positivesplash10-015a-9200000000-97aea4999fbe0d5dd12aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 132V, positivesplash10-067i-9100000000-4ba5915c8412373ceb4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 52V, positivesplash10-0udi-0000009000-90677bb4d4cb194d7bb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0010000900-994357b6692ae6b01544View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0010000900-994357b6692ae6b01544View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-0390300600-ac1e6f12f1f2dd8e7274View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-cbb310d334ec991a7d65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0001309700-eeb33a57ed592ba6ec54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0001309300-02a1479ca6e84ae12d27View in MoNA
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 IDHMDB0009059
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026249
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9546757
PDB IDNot Available
ChEBI ID74986
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(18:1(9Z)/18:1(9Z)/0:0) → Cytidine monophosphate + PE(18:1(9Z)/18:1(9Z))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(18:1(9Z)/18:1(9Z)) → S-Adenosylhomocysteine + PE-NMe(18:1(9Z)/18:1(9Z))details
Enzyme Details
3. Phosphatidylserine decarboxylase proenzyme, mitochondrial
General function:
Not Available
Specific function:
Catalyzes the formation of phosphatidylethanolamine (PtdEtn) from phosphatidylserine (PtdSer). Plays a central role in phospholipid metabolism and in the interorganelle trafficking of phosphatidylserine.
Gene Name:
PISD
Uniprot ID:
Q58DH2
Molecular weight:
47244.0
Reactions
PS(18:1(9Z)/18:1(9Z)) → PE(18:1(9Z)/18:1(9Z)) + Carbon dioxidedetails