Bovine Metabolome Database: Showing metabocard for DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) (BMDB0007586)

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

Record Information

Version

1.0

Creation Date

2016-09-30 23:40:19 UTC

Update Date

2020-05-21 16:26:47 UTC

BMDB ID

BMDB0007586

Secondary Accession Numbers

BMDB07586

Metabolite Identification

Common Name

DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0)

Description

DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0), also known as dg(20:5(5z,8z,11z,14z,17z)/24:0/0:0) or DG(20:5/24:0), belongs to the class of organic compounds known as 1,2-dg(20:5(5z,8z,11z,14z,17z)/24:0/0:0)s. These are dg(20:5(5z,8z,11z,14z,17z)/24:0/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) can be biosynthesized from PA(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) and tetracosanoyl-CoA can be converted into TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:0); which is catalyzed by the enzyme dg(20:5(5z,8z,11z,14z,17z)/24:0/0:0) O-acyltransferase. Furthermore, DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) can be biosynthesized from PA(20:5(5Z,8Z,11Z,14Z,17Z)/24:0); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) and nervonoyl-CoA can be converted into TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:1(15Z)) through the action of the enzyme dg(20:5(5z,8z,11z,14z,17z)/24:0/0:0) O-acyltransferase. Finally, CDP-Ethanolamine and DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) can be converted into cytidine monophosphate and PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) through the action of the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:0) pathway, de novo triacylglycerol biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:1(15Z)) pathway, and phosphatidylethanolamine biosynthesis pe(20:5(5Z,8Z,11Z,14Z,17Z)/24:0) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DG(20:5/24:0)	HMDB
1-Eicosapentaenoyl-2-lignoceroyl-sn-glycerol	HMDB
DAG(20:5/24:0)	HMDB
Diglyceride	HMDB
DG(44:5)	HMDB
Diacylglycerol	HMDB
Diacylglycerol(20:5/24:0)	HMDB
Diacylglycerol(44:5)	HMDB
1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-tetracosanoyl-sn-glycerol	HMDB
DAG(44:5)	HMDB
DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0)	Lipid Annotator

Chemical Formula

C₄₇H₈₂O₅

Average Molecular Weight

727.151

Monoisotopic Molecular Weight

726.616225734

IUPAC Name

(2S)-1-hydroxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propan-2-yl tetracosanoate

Traditional Name

diacylglycerol

CAS Registry Number

Not Available

SMILES

[H][C@](CO)(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C47H82O5/c1-3-5-7-9-11-13-15-17-19-21-22-23-24-26-28-30-32-34-36-38-40-42-47(50)52-45(43-48)44-51-46(49)41-39-37-35-33-31-29-27-25-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,20,27,29,33,35,45,48H,3-5,7,9-11,13,15-17,19,21-26,28,30-32,34,36-44H2,1-2H3/b8-6-,14-12-,20-18-,29-27-,35-33-/t45-/m0/s1

InChI Key

AXXQXIFJLVVPRJ-XTRVTAHOSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Diradylglycerols

Direct Parent

1,2-diacylglycerols

Alternative Parents

Substituents

1,2-acyl-sn-glycerol
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell 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	10.66	ALOGPS
logP	15.53	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	228.49 m³·mol⁻¹	ChemAxon
Polarizability	94.54 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_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-aa684ea5cc6c399a8aa0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-0009900900-98d1bbdc13c57086af36	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a93-0009900900-e1650b35c09fe2d59e7d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fb9-3009124600-86728821bd055a4256f1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-3019122000-c40fe3562333b948b61d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-7968100000-8f6c5ae9c96931512ec9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-b0329d2fbde3d7843971	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-0008800900-18abe8944031c759929e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a93-0008800900-cebffc9a47ce467bb1fc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000000900-b2fdc7efe6f34978ef3b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000000900-b2fdc7efe6f34978ef3b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-0009600100-a0d5a0f9b4175a183753	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1018000900-c0900e22ec001abf9109	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0l6r-3019100100-45fb7212a8bbc474d77e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uxr-3039000000-82e51d222e4441aac47f	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:1(15Z))		Not Available
Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)		Not Available
Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)		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

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0007586

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

53478357

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)/24:0/0:0) → Cytidine monophosphate + PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)	details

Showing metabocard for DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0) (BMDB0007586)

Structure for BMDB0007586 (DG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/0:0))

Enzymes

Reactions