Bovine Metabolome Database: Showing metabocard for DG(16:0/16:0/0:0) (BMDB0007098)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:30:33 UTC

Update Date

2020-05-21 16:28:42 UTC

BMDB ID

BMDB0007098

Secondary Accession Numbers

BMDB07098

Metabolite Identification

Common Name

DG(16:0/16:0/0:0)

Description

DG(16:0/16:0/0:0), also known as DAG(16:0/16:0) or dg(16:0/16:0/0:0), belongs to the class of organic compounds known as 1,2-dg(16:0/16:0/0:0)s. These are dg(16:0/16:0/0:0)s containing a glycerol acylated at positions 1 and 2. Thus, DG(16:0/16:0/0:0) is considered to be a diradylglycerol lipid molecule. DG(16:0/16:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(16:0/16:0/0:0) exists in all living species, ranging from bacteria to humans. In cattle, DG(16:0/16:0/0:0) is involved in the metabolic pathway called the glycerolipid metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-1-(Hydroxymethyl)ethane-1,2-diyl dipalmitate	ChEBI
1,2-Dihexadecanoyl-sn-glycerol	ChEBI
DAG(16:0/16:0)	ChEBI
DAG(32:0)	ChEBI
DG(16:0/16:0)	ChEBI
DG(32:0)	ChEBI
Diacylglycerol(16:0/16:0)	ChEBI
Diacylglycerol(32:0)	ChEBI
(S)-1-(Hydroxymethyl)ethane-1,2-diyl dipalmitic acid	Generator
1,2-Dipalmitoyl-rac-glycerol	HMDB
Diacylglycerol	HMDB
Diglyceride	HMDB
1,2-Dihexadecanoyl-rac-glycerol	HMDB
DG(16:0/16:0/0:0)	Lipid Annotator

Chemical Formula

C₃₅H₆₈O₅

Average Molecular Weight

568.9114

Monoisotopic Molecular Weight

568.506675286

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

30334-71-5

SMILES

Not Available

InChI Identifier

InChI=1S/C35H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33,36H,3-32H2,1-2H3/t33-/m0/s1

InChI Key

JEJLGIQLPYYGEE-XIFFEERXSA-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:82929 )
1,2-dipalmitoylglycerol (CHEBI:82929 )
Diacylglycerols (LMGL02010009 )

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

Not Available

Spectra

Spectrum Type	Description	Splash Key

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:1(9Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(11Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(9Z))		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

HMDB0007098

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024292

KNApSAcK ID

Not Available

Chemspider ID

559127

KEGG Compound ID

C00165

BioCyc ID

DIACYLGLYCEROL

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

4255

PubChem Compound

644078

PDB ID

Not Available

ChEBI ID

82929

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Hepatic triacylglycerol lipase

General function:: Involved in heparin binding
Specific function:: Hepatic lipase has the capacity to catalyze hydrolysis of phospholipids, mono-, di-, and triglycerides, and acyl-CoA thioesters. It is an important enzyme in HDL metabolism. Hepatic lipase binds heparin (By similarity).
Gene Name:: LIPC
Uniprot ID:: Q3SZ79
Molecular weight:: 56826.0

Reactions

TG(16:0/16:0/16:0)[iso] + Water → DG(16:0/16:0/0:0) + Palmitic acid	details
DG(16:0/16:0/0:0) + Water → Palmitic acid + MG(0:0/16:0/0:0)	details

Enzyme Details

2. Cholinephosphotransferase 1

General function:: Lipid transport and metabolism
Specific function:: Catalyzes phosphatidylcholine biosynthesis from CDP-choline. It thereby plays a central role in the formation and maintenance of vesicular membranes (By similarity).
Gene Name:: CHPT1
Uniprot ID:: Q1LZE6
Molecular weight:: 45249.0

Reactions

Citicoline → PC(16:0/16:0) + DG(16:0/16:0/0:0)	details

Enzyme Details

3. 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

4. Diacylglycerol kinase alpha

General function:: Involved in calcium ion binding
Specific function:: Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity.
Gene Name:: DGKA
Uniprot ID:: A0JN54
Molecular weight:: 82672.0

Reactions

DG(16:0/16:0/0:0) → PA(16:0/16:0)	details
DG(16:0/16:0/0:0) + Adenosine triphosphate → PA(16:0/16:0) + ADP	details

Enzyme Details

5. Lipin 1

General function:: Not Available
Specific function:: Not Available
Gene Name:: LPIN1
Uniprot ID:: E1BPE8
Molecular weight:: 102857.0

Reactions

PA(16:0/16:0) + Water → DG(16:0/16:0/0:0) + Hydrogen phosphate	details

Enzyme Details

6. 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(16:0/16:0/0:0) + Palmityl-CoA → TG(16:0/16:0/16:0)[iso] + Coenzyme A	details
DG(16:0/16:0/0:0) + Palmitoleyl CoA → TG(16:0/16:0/16:1(9Z)) + Coenzyme A	details
DG(16:0/16:0/0:0) + Stearoyl-CoA → TG(16:0/16:0/18:0)[iso3] + Coenzyme A	details
DG(16:0/16:0/0:0) + Oleoyl-CoA → TG(16:0/16:0/18:1(9Z)) + Coenzyme A	details
DG(16:0/16:0/0:0) + Gamma-linolenoyl-CoA → TG(16:0/16:0/18:3(6Z,9Z,12Z))[iso3] + Coenzyme A	details
DG(16:0/16:0/0:0) + Eicosanoyl-CoA → TG(16:0/16:0/20:0)[iso3] + Coenzyme A	details
DG(16:0/16:0/0:0) + Gondoyl-CoA → TG(16:0/16:0/20:1(11Z)) + Coenzyme A	details
DG(16:0/16:0/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:0/16:0/20:4(5Z,8Z,11Z,14Z)) + Coenzyme A	details
DG(16:0/16:0/0:0) + Docosanoyl-CoA → TG(16:0/16:0/22:0) + Coenzyme A	details
DG(16:0/16:0/0:0) + Erucoyl-CoA → TG(16:0/16:0/22:1(13Z)) + Coenzyme A	details
DG(16:0/16:0/0:0) + Clupanodonyl CoA → TG(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))[iso3] + Coenzyme A	details
DG(16:0/16:0/0:0) + Tetracosanoyl-CoA → TG(16:0/16:0/24:0) + Coenzyme A	details

Enzyme Details

7. Phospholipid phosphatase 2

General function:: Not Available
Specific function:: Magnesium-independent phospholipid phosphatase that catalyzes the dephosphorylation of a variety of glycerolipid and sphingolipid phosphate esters including phosphatidate/PA, lysophosphatidate/LPA, sphingosine 1-phosphate/S1P and ceramide 1-phosphate/C1P. Has no apparent extracellular phosphatase activity and therefore most probably acts intracellularly. Also acts on N-oleoyl ethanolamine phosphate/N-(9Z-octadecenoyl)-ethanolamine phosphate, a potential physiological compound. Through dephosphorylation of these bioactive lipid mediators produces new bioactive compounds and may regulate signal transduction in different cellular processes (By similarity). Indirectly regulates, for instance, cell cycle G1/S phase transition through its phospholipid phosphatase activity (By similarity).
Gene Name:: PLPP2
Uniprot ID:: Q2HJ61
Molecular weight:: 32328.0

Reactions

PA(16:0/16:0) → DG(16:0/16:0/0:0) + Hydrogen phosphate	details

Showing metabocard for DG(16:0/16:0/0:0) (BMDB0007098)

Structure for BMDB0007098 (DG(16:0/16:0/0:0))

Enzymes

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