Bovine Metabolome Database: Showing metabocard for DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0) (BMDB0007550)

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 23:39:36 UTC

Update Date

2020-05-21 16:28:04 UTC

BMDB ID

BMDB0007550

Secondary Accession Numbers

BMDB07550

Metabolite Identification

Common Name

DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0)

Description

DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0), also known as dg(20:4(8z,11z,14z,17z)/22:0/0:0) or DG(20:4/22:0), belongs to the class of organic compounds known as 1,2-dg(20:4(8z,11z,14z,17z)/22:0/0:0)s. These are dg(20:4(8z,11z,14z,17z)/22:0/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0) can be biosynthesized from PA(20:4(8Z,11Z,14Z,17Z)/22:0) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0) and docosanoyl-CoA can be converted into TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:0); which is catalyzed by the enzyme dg(20:4(8z,11z,14z,17z)/22:0/0:0) O-acyltransferase. Furthermore, DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0) can be biosynthesized from PA(20:4(8Z,11Z,14Z,17Z)/22:0) through the action of the enzyme phosphatidate phosphatase. Finally, DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0) and clupanodonoyl-CoA can be converted into TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme dg(20:4(8z,11z,14z,17z)/22:0/0:0) O-acyltransferase. In cattle, DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:0) pathway and de novo triacylglycerol biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Eicsoatetraenoyl-2-behenoyl-sn-glycerol	HMDB
Diacylglycerol(20:4/22:0)	HMDB
Diacylglycerol(42:4)	HMDB
Diglyceride	HMDB
DG(20:4/22:0)	HMDB
DAG(42:4)	HMDB
Diacylglycerol	HMDB
DAG(20:4/22:0)	HMDB
1-(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-docosanoyl-sn-glycerol	HMDB
DG(42:4)	HMDB
DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0)	Lipid Annotator

Chemical Formula

C₄₅H₈₀O₅

Average Molecular Weight

701.1137

Monoisotopic Molecular Weight

700.60057567

IUPAC Name

(2S)-1-hydroxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propan-2-yl docosanoate

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)CCCCCCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C45H80O5/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/h6,8,12,14,18,20,25,27,43,46H,3-5,7,9-11,13,15-17,19,21-24,26,28-42H2,1-2H3/b8-6-,14-12-,20-18-,27-25-/t43-/m0/s1

InChI Key

WVOUKCXPAOBTMU-KWVLUJTGSA-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	10.6	ALOGPS
logP	15	ChemAxon
logS	-7.9	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	40	ChemAxon
Refractivity	218.18 m³·mol⁻¹	ChemAxon
Polarizability	91.1 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	splash10-014i-0000000900-3824d5719eb36140e8d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03eb-0009003100-f41ca5ea108e223be1fb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03xt-0009000300-3ce8181fbda9d49cd2db	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1009008000-ab8fd78147852ff8be38	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fki-3009000000-759e59393d0024c73655	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udr-3019000000-1b4c7bbbec505b7408fe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000900-19b8554ce51aad925d79	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03eb-0009003100-de3f8b300886885ed58f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03xt-0009000300-d41b5571614fa145dc10	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000900-a37a4a3b9d1bd59ad7af	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000000900-a37a4a3b9d1bd59ad7af	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0160-0009600100-56cf5e67302cb0441275	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-3009023300-8bd13e752d9480502a71	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-3019011000-7751d2dd3dff0fcf367f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0089-7649000000-8478fa43f4e8f45c1510	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)/22:0/22:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:1(13Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:2(13Z,16Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:4(7Z,10Z,13Z,16Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(4Z,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

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0007550

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

53478328

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)/22:0/0:0) → Cytidine monophosphate + PE(20:4(8Z,11Z,14Z,17Z)/22:0)	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(20:4(8Z,11Z,14Z,17Z)/22:0/0:0) + Clupanodonyl CoA → TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme A	details

Showing metabocard for DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0) (BMDB0007550)

Structure for BMDB0007550 (DG(20:4(8Z,11Z,14Z,17Z)/22:0/0:0))

Enzymes

Reactions

Reactions