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

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	Lipid Annotator, HMDB
Diglyceride	Lipid Annotator, HMDB
Diacylglycerol	Lipid Annotator, HMDB
DG(16:0/16:0/0:0)	Lipid Annotator
1,2-dihexadecanoyl-rac-glycerol	Lipid Annotator, HMDB

Chemical Formula

C₃₅H₆₈O₅

Average Molecular Weight

568.9114

Monoisotopic Molecular Weight

568.506675286

IUPAC Name

(2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl hexadecanoate

Traditional Name

diacylglycerol

CAS Registry Number

30334-71-5

SMILES

[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC

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

Property	Value	Source
logP	9.91	ALOGPS
logP	12	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	167.7 m³·mol⁻¹	ChemAxon
Polarizability	75.44 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 (1 TMS) - 70eV, Positive	splash10-0079-6359564000-2102dfe43fc5237291c4	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("DG(16:0/16:0/0:0),1TMS,#1" TMS) - 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	splash10-000i-0000090000-a6675419407dc9ffb69c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-0009090000-0478d1b0b5fd64fb5417	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-0009090000-16d28a11ff66f8962cde	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000090000-83d3342f154c7f0771aa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000090000-83d3342f154c7f0771aa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0019010000-421057e3c0bc72207de0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000090000-2d16a013111540b8e126	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-0008090000-edcaa6212db303a0cd31	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-0008090000-ac3e6604283616c64aa7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02t9-1058090000-6a6e8437c83167cdf120	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-4296130000-5ced98b657cb3473b85e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059i-9872000000-2be02712c2db933cdcae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1055090000-3d1e60ad379348a1a41a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-1091000000-78e78390731db63b8a58	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-0090000000-e4ea24e9dbd60f401937	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer

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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