Bovine Metabolome Database: Showing metabocard for PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) (BMDB0009471)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:43:33 UTC

Update Date

2020-05-21 16:26:47 UTC

BMDB ID

BMDB0009471

Secondary Accession Numbers

BMDB09471

Metabolite Identification

Common Name

PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))

Description

PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)), also known as pe(20:5(5z,8z,11z,14z,17z)/22:4(7z,10z,13z,16z)) or GPEtn(20:5/22:4), 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(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) is considered to be a glycerophosphoethanolamine lipid molecule. PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from PS(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Furthermore, Cytidine monophosphate and PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Furthermore, Cytidine monophosphate and PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-ethanolamine and DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from PS(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) pathway and phosphatidylcholine biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Phophatidylethanolamine(42:9)	HMDB
GPEtn(20:5/22:4)	HMDB
Phophatidylethanolamine(20:5/22:4)	HMDB
PE(42:9)	HMDB
1-Eicosapentaenoyl-2-adrenoyl-sn-glycero-3-phosphoethanolamine	HMDB
PE(20:5/22:4)	HMDB
1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoethanolamine	HMDB
GPEtn(42:9)	HMDB
PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))	Lipid Annotator

Chemical Formula

C₄₇H₇₆NO₈P

Average Molecular Weight

814.082

Monoisotopic Molecular Weight

813.530854925

IUPAC Name

(2-aminoethoxy)[(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxy]phosphinic acid

Traditional Name

PPP

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C47H76NO8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-47(50)56-45(44-55-57(51,52)54-42-41-48)43-53-46(49)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-20,22,24-25,27-28,30-31,33,45H,3-5,7,9-10,15-16,21,23,26,29,32,34-44,48H2,1-2H3,(H,51,52)/b8-6-,13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-,33-31-/t45-/m1/s1

InChI Key

RHMBSGJXCWTXLZ-RFJIFSDASA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

Phosphatidylethanolamines

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 Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoethanolamines (LMGP02010990 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Intracellular membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	8.27	ALOGPS
logP	11.64	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	134.38 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	247.06 m³·mol⁻¹	ChemAxon
Polarizability	93.73 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0003000090-2e707c51e799308b46ee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0003000090-2e707c51e799308b46ee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0w3r-0109110030-1ad1e68687fc67dba2c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000001190-ac20c75c8da9a7d74bea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0229-0003149160-bbd5ae72e5c59af78c52	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0003149110-6458b3d5245d81f63e46	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0003000090-312b3d8260a0b5b40973	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0003000090-312b3d8260a0b5b40973	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0w3r-0109110030-046fe417d9395e90c6cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000001190-e0486f217a80785c9bea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0229-0003149160-3c6c05ce989f7096558f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0003149110-40c750ef302d681b4120	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000001090-76190049a18b0de6e280	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000002290-837682a1d8cac0d8ee03	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0100301910-8117207437619f64676c	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Brain

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
All Tissues	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0009471

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52924691

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not 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(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))	details

Showing metabocard for PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) (BMDB0009471)

Structure for BMDB0009471 (PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)))

Enzymes

Reactions