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DG(16:0/16:0/0:0) (YMDB01127)
| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| 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 |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms |
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| 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 |
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| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations |
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| Organoleptic Properties | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways |
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| KEGG Pathways |
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| SMPDB Reactions | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Reactions |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Intracellular Concentrations |
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| Extracellular Concentrations | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra |
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| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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Enzymes
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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
- 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
- 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