DG(16:0/16:0/0:0) (YMDB01127)

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Identification

YMDB ID

YMDB01127

Name

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

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

DG(16:0/16:0/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(16:0/16:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(+)-D-Dipalmitin
1,2-dipalmitoyl-rac-glycerol
DAG(16:0/16:0)
DAG(32:0)
DG(16:0/16:0)
DG(32:0)
di-O-acylglycerols
Diacylglycerol
Diacylglycerol(16:0/16:0)
Diacylglycerol(32:0)
diacylglycerols
Diglyceride
diglycerides
Hexadecanoic acid, 1-(hydroxymethyl)-1,2-ethanediyl ester
Palmitin, 1,2-di-
(S)-1-(Hydroxymethyl)ethane-1,2-diyl dipalmitate
1,2-Dihexadecanoyl-sn-glycerol
(S)-1-(Hydroxymethyl)ethane-1,2-diyl dipalmitic acid
1,2-Dihexadecanoyl-rac-glycerol
DG(16:0/16:0/0:0)

CAS number

30334-71-5

Weight

Average: 568.9114
Monoisotopic: 568.506675286

InChI Key

JEJLGIQLPYYGEE-MGBGTMOVSA-N

InChI

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-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

diacylglycerol

Chemical Formula

C₃₅H₆₈O₅

SMILES

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

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 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	2.0e-05 g/L	ALOGPS
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	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

mitochondrion
lipid particle
endoplasmic reticulum
nucleus
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Choline metabolism	PW002494
Glycerophospholipid metabolism	PW002493
Lysolipid incorporation into ER PC(16:0/16:0)	PW002784
Triacylglycerol metabolism	PW002695
Triacylglycerol metabolism TG(16:0/16:0/16:0)	PW007758

KEGG Pathways

Glycerophospholipid metabolism

ec00564

SMPDB Reactions

KEGG Reactions

CDP-Ethanolamine + DG(16:0/16:0/0:0) ↔ PE(14:0/16:1(9Z)) + Cytidine monophosphate + hydron

Citicoline + DG(16:0/16:0/0:0) → phosphatidylcholine + Cytidine monophosphate

acyl-CoA + DG(16:0/16:0/0:0) ↔ hydron + TG(18:0/18:0/18:0) + Coenzyme A

LPA(16:0/0:0) + water ↔ DG(16:0/16:0/0:0) + phosphate + hydron

PE(14:0/16:1(9Z)) + 6-O-{alpha-D-mannosyl-(1->2)-alpha-D-mannosyl-(1->6)-2-O-[(2-aminoethyl)phosphoryl]-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl}-O-acyl-1-phosphatidyl-1D-myo-inositol ↔ DG(16:0/16:0/0:0) + 6-[6-(2-aminoethylphosphoryl)-alpha-mannosyl-(1->6)-2-(2-aminoethylphosphoryl)-alpha-mannosyl-(1->6)-alpha-2-(2-aminoethylphosphoryl)mannosyl-(1->4)-alpha-glucosaminyl]-O-acyl-1-phosphatidyl-1D-myo-inositol

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
12500 ± 50 umol/L	SD media with 2% raffinose	37 oC	BY4741	PMID: 19174513
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0079-6359564000-2102dfe43fc5237291c4	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("DG(16:0/16:0/0:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000090000-a6675419407dc9ffb69c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-0009090000-0478d1b0b5fd64fb5417	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-0009090000-16d28a11ff66f8962cde	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000090000-83d3342f154c7f0771aa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000090000-83d3342f154c7f0771aa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0019010000-421057e3c0bc72207de0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000090000-2d16a013111540b8e126	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-0008090000-edcaa6212db303a0cd31	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-0008090000-ac3e6604283616c64aa7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02t9-1058090000-6a6e8437c83167cdf120	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-4296130000-5ced98b657cb3473b85e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059i-9872000000-2be02712c2db933cdcae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1055090000-3d1e60ad379348a1a41a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-1091000000-78e78390731db63b8a58	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-0090000000-e4ea24e9dbd60f401937	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	18035
HMDB ID	HMDB07098
Pubchem Compound ID	99931
Kegg ID	C00165
ChemSpider ID	559127
FOODB ID	FDB024292
Wikipedia ID	Not Available
BioCyc ID	DIACYLGLYCEROL

Enzymes

Protein Details

1. Diacylglycerol O-acyltransferase 1

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for storage lipid synthesis. May be involved in lipid particle synthesis from the endoplasmic reticulum and ergosterol biosynthesis
Gene Name:: DGA1
Uniprot ID:: Q08650
Molecular weight:: 47710.89844

Reactions

Acyl-CoA + 1,2-diacylglycerol → CoA + triacylglycerol.

Protein Details

2. Probable 1-acyl-sn-glycerol-3-phosphate acyltransferase

General function:: Involved in acyltransferase activity
Specific function:: May be an acyltransferase with an altered substrate specificity that enables it to use a C-26-CoA in place of the C-16 or C-18-CoAs used by the wild-type protein
Gene Name:: SLC1
Uniprot ID:: P33333
Molecular weight:: 33886.69922

Reactions

Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate → CoA + 1,2-diacyl-sn-glycerol 3-phosphate.

Protein Details

3. Lysophospholipid acyltransferase

General function:: Involved in 1-acylglycerol-3-phosphate O-acyltransferas
Specific function:: Membrane-bound O-acyltransferase that mediates the incorporation of unsaturated acyl chains into the sn-2 position of phopholipids. Preferentially acylates lysophosphocholine, but also lysophosphoethanolamine and lysophosphatidylglycerol
Gene Name:: ALE1
Uniprot ID:: Q08548
Molecular weight:: 72227.39844

Reactions

Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate → CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Acyl-CoA + 1-acyl-sn-glycero-3-phosphocholine → CoA + 1,2-diacyl-sn-glycero-3-phosphocholine.
Acyl-CoA + 1-acyl-sn-glycero-3-phosphoethanolamine → CoA + 1,2-diacyl-sn-glycero-3-phosphoethanolamine.

Protein Details

4. CTP-dependent diacylglycerol kinase 1

General function:: Involved in transferase activity, transferring phosphorus-containing groups
Specific function:: Involved in pre-tRNA splicing. CTP- dependent diacylglycerol kinase that catalyzes the phosphorylation of diacylglycerol (DAG) to phosphatidate (PA). Controls phosphatidate levels at the nuclear envelope. Counteracts the activity of PAH1/SMP2. Involved in the resistance to nickel chloride and nalidixic acid. May be involved in vesicle trafficking between the endoplasmic reticulum and the Golgi apparatus
Gene Name:: DGK1
Uniprot ID:: Q12382
Molecular weight:: 32839.80078

Reactions

CTP + 1,2-diacyl-sn-glycerol → CDP + 1,2-diacyl-sn-glycerol 3-phosphate.

Protein Details

5. Cholinephosphotransferase 1

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the cholinephosphotransferase might participate in the transport process
Gene Name:: CPT1
Uniprot ID:: P17898
Molecular weight:: 44829.0

Reactions

CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.

Protein Details

6. Phosphatidate cytidylyltransferase

General function:: Involved in transferase activity, transferring phosphorus-containing groups
Specific function:: Supplies CDP-diacylglycerol, which may play an important role as both a precursor to phosphoinositide biosynthesis in the plasma membrane and as a negative effector of phosphatidylinositol 4-kinase activity, thereby exerting an effect on cell proliferation via a lipid-dependent signal transduction cascade
Gene Name:: CDS1
Uniprot ID:: P38221
Molecular weight:: 51822.39844

Reactions

CTP + phosphatidate → diphosphate + CDP-diacylglycerol.

Protein Details

7. Sterol esterase TGL1

General function:: Involved in lipid metabolic process
Specific function:: Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism. May have weak lipase activity toward triglycerides upon some conditions, however, the relevance of such activity is unclear in vivo
Gene Name:: TGL1
Uniprot ID:: P34163
Molecular weight:: 62978.39844

Reactions

A steryl ester + H(2)O → a sterol + a fatty acid.

Protein Details

8. Lipase 2

General function:: Involved in hydrolase activity, acting on ester bonds
Specific function:: Lipolytic activity towards triacylglycerols and diacylglycerols with short-chain fatty acids
Gene Name:: TGL2
Uniprot ID:: P54857
Molecular weight:: 37499.89844

Reactions

Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.

Protein Details

9. Lipase 3

General function:: Involved in metabolic process
Specific function:: Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process
Gene Name:: TGL3
Uniprot ID:: P40308
Molecular weight:: 73611.79688

Reactions

Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.

Protein Details

10. Lipase 5

General function:: Involved in metabolic process
Specific function:: Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:: TGL5
Uniprot ID:: Q12043
Molecular weight:: 84715.10156

Reactions

Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.

Protein Details

11. Lipase 4

General function:: Involved in metabolic process
Specific function:: Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:: TGL4
Uniprot ID:: P36165
Molecular weight:: 102716.0

Reactions

Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.

Protein Details

12. Phosphatidic acid phosphohydrolase 1

General function:: vacuole fusion, non-autophagic
Specific function:: Mg(2+)-dependent phosphatidate (PA) phosphatase which catalyzes the dephosphorylation of PA to yield diacylglycerol. Required for de novo lipid synthesis and formation of lipid droplets. Controles transcription of phospholipid biosynthetic genes and nuclear structure by regulating the amount of membrane present at the nuclear envelope. Involved in plasmid maintenance, in respiration and in cell proliferation.
Gene Name:: PAH1
Uniprot ID:: P32567
Molecular weight:: 95029.985

Reactions

Protein Details

13. Phosphatidate cytidylyltransferase, mitochondrial

General function:: CDP-diacylglycerol biosynthetic process
Specific function:: Catalyzes the formation of CDP-diacylglycerol (CDP-DAG) from phosphatidic acid (PA) in the mitochondrial inner membrane. Required for the biosynthesis of the dimeric phospholipid cardiolipin, which stabilizes supercomplexes of the mitochondrial respiratory chain in the mitochondrial inner membrane.
Gene Name:: TAM41
Uniprot ID:: P53230
Molecular weight:: 44199.33

Reactions

Protein Details

14. Lysophosphatidic acid:oleoyl-CoA acyltransferase 1

General function:: lipid particle organization
Specific function:: Acyl-CoA-dependent lysophosphatidic acid acyltransferase with preference for oleoyl-CoA. Involved in triacylglyceride homeostasis and lipid droplet formation. Involved in vacuolar protein sorting.
Gene Name:: LOA1
Uniprot ID:: Q06508
Molecular weight:: 33815.635

Reactions

Structure for #<Compound:0x9bd922a4>

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