Bovine Metabolome Database: Showing metabocard for DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) (BMDB0007698)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:42:36 UTC

Update Date

2020-05-21 16:28:07 UTC

BMDB ID

BMDB0007698

Secondary Accession Numbers

BMDB07698

Metabolite Identification

Common Name

DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0)

Description

DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0), also known as DAG(22:4/22:4) or dg(22:4(7z,10z,13z,16z)/22:4(7z,10z,13z,16z)/0:0), belongs to the class of organic compounds known as 1,2-dg(22:4(7z,10z,13z,16z)/22:4(7z,10z,13z,16z)/0:0)s. These are dg(22:4(7z,10z,13z,16z)/22:4(7z,10z,13z,16z)/0:0)s containing a glycerol acylated at positions 1 and 2. Thus, DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) can be converted into cytidine monophosphate and PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Furthermore, CDP-Choline and DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) can be converted into cytidine monophosphate and PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) through the action of the enzyme choline/ethanolaminephosphotransferase. Furthermore, DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) can be biosynthesized from PA(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) and adrenoyl-CoA can be converted into TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)); which is mediated by the enzyme dg(22:4(7z,10z,13z,16z)/22:4(7z,10z,13z,16z)/0:0) O-acyltransferase. Furthermore, DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) can be biosynthesized from PA(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)); which is mediated by the enzyme phosphatidate phosphatase. Finally, DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) and nervonoyl-CoA can be converted into TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z)); which is mediated by the enzyme dg(22:4(7z,10z,13z,16z)/22:4(7z,10z,13z,16z)/0:0) O-acyltransferase. In cattle, DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) is involved in a few metabolic pathways, which include phosphatidylcholine biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) pathway, de novo triacylglycerol biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) pathway, and de novo triacylglycerol biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DAG(22:4/22:4)	ChEBI
DAG(22:4N6/22:4N6)	ChEBI
DAG(22:4W6/22:4W6)	ChEBI
DAG(44:8)	ChEBI
DG(22:4/22:4)	ChEBI
DG(22:4/22:4/0:0)	ChEBI
DG(22:4N6/22:4N6)	ChEBI
DG(22:4W6/22:4W6)	ChEBI
DG(44:8)	ChEBI
Diacylglycerol(22:4/22:4)	ChEBI
Diacylglycerol(22:4n6/22:4n6)	ChEBI
Diacylglycerol(22:4W6/22:4W6)	ChEBI
1,2-Diadrenoyl-rac-glycerol	HMDB
Diacylglycerol	HMDB
Diacylglycerol(44:8)	HMDB
Diglyceride	HMDB
1,2-Di(7Z,10Z,13Z,16Z-docosatetraenoyl)-rac-glycerol	HMDB
DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0)	Lipid Annotator

Chemical Formula

C₄₇H₇₆O₅

Average Molecular Weight

721.1033

Monoisotopic Molecular Weight

720.569275542

IUPAC Name

(2S)-1-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-hydroxypropan-2-yl (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoate

Traditional Name

1,2-diadrenoyl-rac-glycerol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C47H76O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-46(49)51-44-45(43-48)52-47(50)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,45,48H,3-10,15-16,21-22,27-28,33-44H2,1-2H3/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-/t45-/m0/s1

InChI Key

HHYKAFPKWFOYAT-AWFPJDAOSA-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

1,2-diacyl-sn-glycerol (CHEBI:84440 )
Diacylglycerols (LMGL02010298 )

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	9.34	ALOGPS
logP	14.44	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	38	ChemAxon
Refractivity	231.84 m³·mol⁻¹	ChemAxon
Polarizability	89.32 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	splash10-00y0-1009110400-4b1af64ac59d9b0e895d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ri-2039242100-f62dcd6ccd8c818a4f75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00y0-3089375000-4f017e4076de3ffdcc01	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02ar-0009100300-56ddc37e827b3f699e84	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-1009100000-e811561e6641f7f100e7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2019000000-009c245ff6ef5a9cccbf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-edaee7c17dfb50139248	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-0008000900-04885c04edf74c958a55	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0008000900-13ff2a764698cda249b3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-6314234900-fc42ff4409e5d24dfce6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0670-2019121000-b67b6e7ae2d15b22f9cf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-017r-1329030000-cf6f85cb2be7b251dca1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-fbd6dbf6d07360c0bc22	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000900-fbd6dbf6d07360c0bc22	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0001900100-5e4e5bf88d053b863c61	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009100700-b6202c408d4a78361e1c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-3009000000-5f2b617a61ddcf04cfcf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-3009000000-96893c0adaadeed24315	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/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

HMDB0007698

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024891

KNApSAcK ID

Not Available

Chemspider ID

7822913

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9543963

PDB ID

Not Available

ChEBI ID

84440

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(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))	details

Enzyme Details

2. Diacylglycerol O-acyltransferase 1

General function:: Not Available
Specific function:: Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:: DGAT1
Uniprot ID:: Q8MK44
Molecular weight:: 55602.0

Reactions

DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) + Clupanodonyl CoA → TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme A	details

Showing metabocard for DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0) (BMDB0007698)

Structure for BMDB0007698 (DG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/0:0))

Enzymes

Reactions

Reactions