Bovine Metabolome Database: Showing metabocard for DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) (BMDB0007556)

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 23:39:43 UTC

Update Date

2020-05-21 16:26:46 UTC

BMDB ID

BMDB0007556

Secondary Accession Numbers

BMDB07556

Metabolite Identification

Common Name

DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)

Description

DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), also known as DAG(20:4/22:6) or dg(20:4(8z,11z,14z,17z)/22:6(4z,7z,10z,13z,16z,19z)/0:0), belongs to the class of organic compounds known as 1,2-dg(20:4(8z,11z,14z,17z)/22:6(4z,7z,10z,13z,16z,19z)/0:0)s. These are dg(20:4(8z,11z,14z,17z)/22:6(4z,7z,10z,13z,16z,19z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) can be converted into cytidine monophosphate and PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) can be biosynthesized from PA(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) can be biosynthesized from PA(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme phosphatidate phosphatase. Finally, DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) and docosahexaenoyl-CoA can be converted into TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme dg(20:4(8z,11z,14z,17z)/22:6(4z,7z,10z,13z,16z,19z)/0:0) O-acyltransferase. In cattle, DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is involved in a few metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway, de novo triacylglycerol biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0) pathway, and de novo triacylglycerol biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DAG(20:4/22:6)	HMDB
Diacylglycerol(42:10)	HMDB
Diglyceride	HMDB
Diacylglycerol(20:4/22:6)	HMDB
DAG(42:10)	HMDB
DG(42:10)	HMDB
DG(20:4/22:6)	HMDB
Diacylglycerol	HMDB
1-(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol	HMDB
1-Eicsoatetraenoyl-2-docosahexaenoyl-sn-glycerol	HMDB
DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)	Lipid Annotator

Chemical Formula

C₄₅H₆₈O₅

Average Molecular Weight

689.0184

Monoisotopic Molecular Weight

688.506675286

IUPAC Name

(2S)-1-hydroxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

Traditional Name

diacylglycerol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C45H68O5/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-45(48)50-43(41-46)42-49-44(47)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,22,24-25,27-28,30,34,36,43,46H,3-4,9-10,15-16,21,23,26,29,31-33,35,37-42H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-,36-34-/t43-/m0/s1

InChI Key

YCNDIMXDDFVUAL-ZZJJVMTHSA-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	8.41	ALOGPS
logP	12.83	ChemAxon
logS	-7.4	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	34	ChemAxon
Refractivity	224.87 m³·mol⁻¹	ChemAxon
Polarizability	82.81 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	splash10-0a4i-0000000900-4d54919a524ef91c6f8f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01w0-0009003000-225871fffc4b1f421c18	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06ri-0009001300-28e926a8025653e5fc7d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-4f89aa3e58d4acf53579	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000900-4f89aa3e58d4acf53579	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a60-0009600100-71fbbc04fd538d749494	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-e9c6fca1c39c4d12b999	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01w0-0009003000-95abc25472df64058c02	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06ri-0009001300-f7494571f964e7e8c01f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0024029000-14a913c88fe352ba0af0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2059012000-19eb0731f22f8c842131	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0189010000-3f76d9d8d4d6e3f6b276	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0019007000-c5deac7d282c74a5cfcd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uki-4029000000-0989bf3400d0aac71b50	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zi0-5139000000-8b919593182995e4cbf9	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))		Not Available
Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))		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

HMDB0007556

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

53478334

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(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) → Cytidine monophosphate + PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))	details

Showing metabocard for DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) (BMDB0007556)

Structure for BMDB0007556 (DG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0))

Enzymes

Reactions