DG(14:0/14:0/0:0) (YMDB12737)

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Identification

YMDB ID

YMDB12737

Name

DG(14:0/14:0/0:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

DG(14:0/14:0/0:0) 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(14:0/14:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2,3-Dimyristin
2,3-Ditetradecanoyl-sn-glycerol
DG 0:0/14:0/14:0

CAS number

Not Available

Weight

Average: 512.816
Monoisotopic: 512.444075032

InChI Key

JFBCSFJKETUREV-GDLZYMKVSA-N

InChI

InChI=1S/C31H60O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-30(33)35-28-29(27-32)36-31(34)26-24-22-20-18-16-14-12-10-8-6-4-2/h29,32H,3-28H2,1-2H3/t29-/m1/s1

IUPAC Name

(2R)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl tetradecanoate

Traditional IUPAC Name

(2R)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl tetradecanoate

Chemical Formula

C₃₁H₆₀O₅

SMILES

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

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

2,3-diacyl-sn-glycerol (CHEBI:77392 )

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	2.8e-05 g/L	ALOGPS
logP	9.19	ALOGPS
logP	10.22	ChemAxon
logS	-7.3	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	30	ChemAxon
Refractivity	149.29 m³·mol⁻¹	ChemAxon
Polarizability	67.49 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

Cytoplasm
Endoplasmic reticulum

Organoleptic Properties

Not Available

SMPDB Pathways

Lysolipid incorporation into ER	PW002532
Lysolipid incorporation into ER PC(14:0/14:0)	PW002783
Lysolipid incorporation into ER PC(18:2(9Z,11Z)/18:2(9Z,11Z))	PW002789
Triacylglycerol metabolism TG(14:0/14:0/14:0)	PW007615
Triacylglycerol metabolism TG(14:0/14:0/25:0)	PW007819

KEGG Pathways

Not Available

SMPDB Reactions

Citicoline + DG(14:0/14:0/0:0) → Cytidine monophosphate + hydron + PC(14:0/14:0)

Citicoline + DG(14:0/14:0/0:0) → Cytidine monophosphate + hydron + PC(18:2(9Z,11Z)/18:2(9Z,11Z))

PA(14:0/14:0) + water → DG(14:0/14:0/0:0) + phosphate

DG(14:0/14:0/0:0) + Cytidine triphosphate → PA(14:0/14:0) + hydron + CDP

long-chain fatty acyl-CoA + DG(14:0/14:0/0:0) → Coenzyme A + Trimyristin

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0092050000-42e5100db3d0672cfdb2	JSpectraViewer

References

References:

Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	77392
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

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. 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

3. 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

4. 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

5. 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

6. 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

7. 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

8. 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

9. 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

Structure for #<Compound:0xae9c2e54>

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