Bovine Metabolome Database: Showing metabocard for PE(16:0/16:0) (BMDB0008923)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:32:08 UTC

Update Date

2020-05-21 16:28:41 UTC

BMDB ID

BMDB0008923

Secondary Accession Numbers

BMDB08923

Metabolite Identification

Common Name

PE(16:0/16:0)

Description

PE(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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Dihexadecanoyl-sn-glycero-3-phosphoethanolamine	ChEBI
1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine zwitterion	ChEBI
2-Ammonioethyl (2R)-2,3-bis(palmitoyloxy)propyl phosphate	ChEBI
2-Ammonioethyl (2R)-2,3-bis(palmitoyloxy)propyl phosphoric acid	Generator
1,2-Dipalmitoyl-rac-glycerophosphoethanolamine	HMDB
DHPE	HMDB
DPPE	HMDB
1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamine	HMDB
1,2-Dipalmitoyl-3-phosphatidylethanolamine	HMDB
1,2-Dipalmitoyl-3-phosphatidylethanolamine, (+-)-isomer	HMDB
1,2-Dipalmitoyl-3-phosphatidylethanolamine, ion(1-)	HMDB
Dipalmitoyl cephalin	HMDB
Phosphatidylethanolamine dipalmitoate	HMDB
1,2-Dipalmitoyl-3-phosphatidylethanolamine, (R)-isomer	HMDB
Dipalmitoyl phosphatidylethanolamine	HMDB
PE(32:0)	HMDB
Phophatidylethanolamine(16:0/16:0)	HMDB
1,2-Dipalmitoyl-rac-glycero-3-phosphoethanolamine	HMDB
GPEtn(32:0)	HMDB
Phophatidylethanolamine(32:0)	HMDB
1,2-Dihexadecanoyl-rac-glycero-3-phosphoethanolamine	HMDB
GPEtn(16:0/16:0)	HMDB
1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine	HMDB
PE(16:0/16:0)	Lipid Annotator
1,2-Dipalmitoyl-glycero-3-phosphoethanolamine	HMDB

Chemical Formula

C₃₇H₇₄NO₈P

Average Molecular Weight

691.972

Monoisotopic Molecular Weight

691.515205345

IUPAC Name

(2-aminoethoxy)[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphinic acid

Traditional Name

DPPE

CAS Registry Number

923-61-5

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 Key

SLKDGVPOSSLUAI-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.

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

1,2-diacyl-sn-glycero-3-phosphoethanolamine (CHEBI:73127 )
Diacylglycerophosphoethanolamines (LMGP02010037 )

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	8.08	ALOGPS
logP	10.45	ChemAxon
logS	-6.9	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	39	ChemAxon
Refractivity	191 m³·mol⁻¹	ChemAxon
Polarizability	85.59 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-Ion Trap , Negative	splash10-0a4i-0090100000-78393dc4e019ebd83091	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-0udi-0000090000-069925af450b3d115abb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - IT 30V, positive	splash10-0udi-0000092000-56ad77c14f3dd6abfc2a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 16V, positive	splash10-0006-0000029000-27be419812bef5a711b8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 26V, positive	splash10-0udi-0000091000-bcc33889face46932592	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 37V, positive	splash10-0udi-0000090000-c5fc59cd33b54d2b0ca9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 48V, positive	splash10-0udi-0000090000-705a17812444ed5b05d9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0010009000-a6e178ef3224d9865bff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0010009000-a6e178ef3224d9865bff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-0390306000-ad2b7adbfe5f6633b9d6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000019000-814aefc198261f6d39f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udl-0001397000-5c50d43804f2de04b695	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0001393000-fa8208f710210c1fb8b5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000010900-bb7978dcbee6464346df	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03k9-0000022900-6efdc1241c22750b2501	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0100119100-d1161af391f6b033c241	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0010009000-0eb6e92cae6cb86893c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0010009000-0eb6e92cae6cb86893c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-0390306000-ed49698119adb877ef12	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000019000-9ed53d8418cab57ddd34	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udl-0001397000-861b87a9fc2981fd8bdf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0001393000-5efc530efdb379be340d	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Brain

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(16:0/16:0)		Not Available
Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)		Not Available
Phospholipid Biosynthesis		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

HMDB0008923

DrugBank ID

DB01728

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB026113

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

445468

PDB ID

PEF

ChEBI ID

73005

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(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

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

Structure for BMDB0008923 (PE(16:0/16:0))

Enzymes

Reactions

Reactions

Reactions

Reactions