Record Information
Version1.0
Created at2020-03-30 18:01:32 UTC
Updated at2020-12-07 19:07:55 UTC
CannabisDB IDCDB001069
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePE(18:0/20:0)
DescriptionPE(18:0/20:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PE(18:0/20:0), in particular, consists of one octadecanoyl chain to the C-1 atom, and one eicosanoyl to the C-2 atom. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. This compound is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
Phophatidylethanolamine(18:0/20:0)HMDB
GPEtn(18:0/20:0)HMDB
1-Stearoyl-2-arachidonyl-sn-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(38:0)HMDB
GPEtn(38:0)HMDB
1-Octadecanoyl-2-eicosanoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(38:0)HMDB
PE(18:0/20:0)Lipid Annotator
Chemical FormulaC43H86NO8P
Average Molecular Weight776.13
Monoisotopic Molecular Weight775.6091
IUPAC Name(2-aminoethoxy)[(2R)-2-(icosanoyloxy)-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2-(icosanoyloxy)-3-(octadecanoyloxy)propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C43H86NO8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-43(46)52-41(40-51-53(47,48)50-38-37-44)39-49-42(45)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h41H,3-40,44H2,1-2H3,(H,47,48)/t41-/m1/s1
InChI KeyTZINTCMFTOUPSN-VQJSHJPSSA-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
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.2ALOGPS
logP13.12ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.38 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity218.61 m³·mol⁻¹ChemAxon
Polarizability97.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPE(18:0/20:0), TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0011000900-4b0862622120ab996c712017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000900-4b0862622120ab996c712017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03lr-0399410600-88923c0936b3cdd8fb632017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000001900-996a5650ae3eef48ad472017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0003419700-422ddc13e256003640d42017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0003419300-d7605597e8ce67bf3e952017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000001900-299d3d516bc91c900ff92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0000001900-5b9159548ba9c942e5672021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0100201900-7ab1be3fbddeff2374152021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000001900-0b1fcb7771147698de922021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0003419700-f928cce44e52cfc25fc52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0003419300-46b44531606a166ba6fc2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0011000900-a044e06b5d24a28c67b92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000900-a044e06b5d24a28c67b92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03lr-0399410600-1375b4136333737217352021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Calcium-dependent phospholipase A2PLA2G51p36-p34P39877 details
Group IIF secretory phospholipase A2PLA2G2F1p35Q9BZM2 details
Cytosolic phospholipase A2PLA2G4A1q25P47712 details
Phospholipase A2PLA2G1B12q23-q24.1P04054 details
Group XIIB secretory phospholipase A2-like proteinPLA2G12BQ9BX93 details
Group 10 secretory phospholipase A2PLA2G1016p13.1-p12O15496 details
Group IIE secretory phospholipase A2PLA2G2E1p36.13Q9NZK7 details
85/88 kDa calcium-independent phospholipase A2PLA2G622q13.1O60733 details
Group IID secretory phospholipase A2PLA2G2D1p36.12Q9UNK4 details
Phospholipase D2PLD217p13.1O14939 details
Phosphatidylethanolamine N-methyltransferasePEMT17p11.2Q9UBM1 details
Phospholipase D1PLD13q26Q13393 details
Group 3 secretory phospholipase A2PLA2G322q12.2Q9NZ20 details
Probable phospholipid-transporting ATPase IGATP11CQ8NB49 details
Probable phospholipid-transporting ATPase IHATP11A13q34P98196 details
Probable phospholipid-transporting ATPase VAATP10A15q11.2O60312 details
Probable phospholipid-transporting ATPase ICATP8B118q21-q22|18q21.31O43520 details
Probable phospholipid-transporting ATPase IIAATP9A20q13.2O75110 details
Probable phospholipid-transporting ATPase VDATP10D4p12Q9P241 details
Probable phospholipid-transporting ATPase IBATP8A213q12Q9NTI2 details
Probable phospholipid-transporting ATPase IAATP8A14p13Q9Y2Q0 details
Probable phospholipid-transporting ATPase IMATP8B415q21.2Q8TF62 details
Probable phospholipid-transporting ATPase IFATP11B3q27Q9Y2G3 details
Probable phospholipid-transporting ATPase IKATP8B319p13.3O60423 details
Phospholipid scramblase 1PLSCR13q23O15162 details
Phosphatidylserine decarboxylase proenzymePISD22q12.2Q9UG56 details
Choline/ethanolaminephosphotransferase 1CEPT11p13.3Q9Y6K0 details
Phospholipase D3PLD319q13.2Q8IV08 details
Phospholipase D4PLD414q32.33Q96BZ4 details
Phospholipid scramblase 2PLSCR23q24Q9NRY7 details
Phospholipid scramblase 3PLSCR317p13.1Q9NRY6 details
Phospholipid scramblase 4PLSCR43q24Q9NRQ2 details
Phospholipid scramblase family member 5PLSCR53q24A0PG75 details
Probable phospholipid-transporting ATPase VBATP10B5q34O94823 details
Probable phospholipid-transporting ATPase IDATP8B21q21.3P98198 details
Abhydrolase domain-containing protein 4ABHD414q11.2Q8TB40 details
N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase DNAPEPLD7q22.1Q6IQ20 details
Phosphatidylethanolamine-binding protein 1PEBP112q24.23P30086 details
Phosphatidylethanolamine-binding protein 4PEBP48p21.3Q96S96 details
Ethanolaminephosphotransferase 1EPT12p23.3Q9C0D9 details
Cytosolic phospholipase A2 betaPLA2G4B15q11.2-q21.3P0C869 details
Phospholipase D1 variantQ59EA4 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Probable phospholipid-transporting ATPase IGATP11CQ8NB49 details
Probable phospholipid-transporting ATPase IHATP11A13q34P98196 details
Probable phospholipid-transporting ATPase VAATP10A15q11.2O60312 details
Probable phospholipid-transporting ATPase ICATP8B118q21-q22|18q21.31O43520 details
Probable phospholipid-transporting ATPase IIAATP9A20q13.2O75110 details
Probable phospholipid-transporting ATPase VDATP10D4p12Q9P241 details
Probable phospholipid-transporting ATPase IBATP8A213q12Q9NTI2 details
Probable phospholipid-transporting ATPase IAATP8A14p13Q9Y2Q0 details
Probable phospholipid-transporting ATPase IMATP8B415q21.2Q8TF62 details
Probable phospholipid-transporting ATPase IFATP11B3q27Q9Y2G3 details
Probable phospholipid-transporting ATPase IKATP8B319p13.3O60423 details
Probable phospholipid-transporting ATPase VBATP10B5q34O94823 details
Probable phospholipid-transporting ATPase IDATP8B21q21.3P98198 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Calcium-dependent phospholipase A2PLA2G51p36-p34P39877 details
Group IIF secretory phospholipase A2PLA2G2F1p35Q9BZM2 details
Phospholipase A2PLA2G1B12q23-q24.1P04054 details
Group XIIB secretory phospholipase A2-like proteinPLA2G12BQ9BX93 details
Group 10 secretory phospholipase A2PLA2G1016p13.1-p12O15496 details
Group IIE secretory phospholipase A2PLA2G2E1p36.13Q9NZK7 details
Group IID secretory phospholipase A2PLA2G2D1p36.12Q9UNK4 details
Probable phospholipid-transporting ATPase IGATP11CQ8NB49 details
Probable phospholipid-transporting ATPase IHATP11A13q34P98196 details
Probable phospholipid-transporting ATPase VAATP10A15q11.2O60312 details
Probable phospholipid-transporting ATPase ICATP8B118q21-q22|18q21.31O43520 details
Probable phospholipid-transporting ATPase IIAATP9A20q13.2O75110 details
Probable phospholipid-transporting ATPase VDATP10D4p12Q9P241 details
Probable phospholipid-transporting ATPase IBATP8A213q12Q9NTI2 details
Probable phospholipid-transporting ATPase IAATP8A14p13Q9Y2Q0 details
Probable phospholipid-transporting ATPase IMATP8B415q21.2Q8TF62 details
Probable phospholipid-transporting ATPase IFATP11B3q27Q9Y2G3 details
Probable phospholipid-transporting ATPase IKATP8B319p13.3O60423 details
Choline/ethanolaminephosphotransferase 1CEPT11p13.3Q9Y6K0 details
Probable phospholipid-transporting ATPase VBATP10B5q34O94823 details
Probable phospholipid-transporting ATPase IDATP8B21q21.3P98198 details
N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase DNAPEPLD7q22.1Q6IQ20 details
Ethanolaminephosphotransferase 1EPT12p23.3Q9C0D9 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Phospholipase A2PLA2G1B12q23-q24.1P04054 details
Phospholipase D2PLD217p13.1O14939 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Phospholipase A2PLA2G1B12q23-q24.1P04054 details
Group 10 secretory phospholipase A2PLA2G1016p13.1-p12O15496 details
Concentrations Data
Not Available
HMDB IDHMDB0008998
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB026188
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound449007
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 82 proteins in total.

Enzymes

General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Molecular weight:
16546.1
General function:
Involved in protein binding
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:
PLD2
Uniprot ID:
O14939
Molecular weight:
104656.485

Transporters

General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP11C
Uniprot ID:
Q8NB49
Molecular weight:
129476.0
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP11A
Uniprot ID:
P98196
Molecular weight:
129754.6
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP10A
Uniprot ID:
O60312
Molecular weight:
167686.6
General function:
Involved in ATP binding
Specific function:
May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids in the canicular membrane. May have a role in transport of bile acids into the canaliculus, uptake of bile acids from intestinal contents into intestinal mucosa or both
Gene Name:
ATP8B1
Uniprot ID:
O43520
Molecular weight:
143694.1
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP9A
Uniprot ID:
O75110
Molecular weight:
118581.5
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP10D
Uniprot ID:
Q9P241
Molecular weight:
160272.3
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP8A2
Uniprot ID:
Q9NTI2
Molecular weight:
129240.4
General function:
Involved in ATP binding
Specific function:
May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids, mainly in secretory vesicles
Gene Name:
ATP8A1
Uniprot ID:
Q9Y2Q0
Molecular weight:
131368.2
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP8B4
Uniprot ID:
Q8TF62
Molecular weight:
135867.0
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP11B
Uniprot ID:
Q9Y2G3
Molecular weight:
134188.6

Only showing the first 10 proteins. There are 82 proteins in total.