Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-21 13:25:20 UTC |
---|
Update Date | 2022-11-30 19:10:24 UTC |
---|
HMDB ID | HMDB0056197 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | DG(18:1n9/0:0/18:1n9) |
---|
Description | DG(18:1n9/0:0/18:1n9) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at the C-1 C-2, or C-3 positions. DG(18:1n9/0:0/18:1n9), in particular, consists of two chains of oleic acid at the C-1 and C-3 positions. The oleic acid moieties are derived from vegetable oils, especially olive and canola oil. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol. Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-3 position. |
---|
Structure | [H]C(O)(COC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-35-37(40)36-44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18- |
---|
Synonyms | Value | Source |
---|
1,3-Di-(9Z-octadecenoyl)-glycerol | ChEBI | 1,3-Diolein | ChEBI | 2-Hydroxy-1,3-propanediyl dioleate | ChEBI | DAG(18:1/0:0/18:1) | ChEBI | DAG(18:1OMEGA9/0:0/18:1OMEGA9) | ChEBI | DAG(36:2) | ChEBI | DG(18:1(OMEGA-9)/0:0/18:1(OMEGA-9)) | ChEBI | DG(18:1/0:0/18:1) | ChEBI | DG(18:1OMEGA9/0:0/18:1OMEGA9) | ChEBI | DG(36:2) | ChEBI | Diacylglycerol(18:1/0:0/18:1) | ChEBI | Diacylglycerol(18:1omega9/0:0/18:1omega9) | ChEBI | Diacylglycerol(36:2) | ChEBI | 2-Hydroxy-1,3-propanediyl dioleic acid | Generator | 1,3-Di-(9Z)-octadecenoylglycerol | HMDB | 1,3-Di-(cis-9-octadecenoyl)glycerol | HMDB | Diacylglycerol(18:1W9/0:0/18:1W9) | HMDB | 1-Oleoyl-3-oleoyl-sn-glycerol | HMDB | DAG(18:1W9/0:0/18:1W9) | HMDB | Diglyceride | HMDB | DG(18:1W9/0:0/18:1W9) | HMDB | Diacylglycerol(18:1n9/0:0/18:1n9) | HMDB | Diacylglycerol | HMDB | 1-(9Z-Octadecenoyl)-3-(9Z-octadecenoyl)-sn-glycerol | HMDB | DAG(18:1N9/0:0/18:1N9) | HMDB | DG(18:1n9/0:0/18:1n9) | Lipid Annotator |
|
---|
Chemical Formula | C39H72O5 |
---|
Average Molecular Weight | 620.986 |
---|
Monoisotopic Molecular Weight | 620.537975414 |
---|
IUPAC Name | 2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl (9Z)-octadec-9-enoate |
---|
Traditional Name | 2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl (9Z)-octadec-9-enoate |
---|
CAS Registry Number | Not Available |
---|
SMILES | [H]C(O)(COC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC |
---|
InChI Identifier | InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-35-37(40)36-44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18- |
---|
InChI Key | DRAWQKGUORNASA-CLFAGFIQSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as 1,3-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 3. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Glycerolipids |
---|
Sub Class | Diradylglycerols |
---|
Direct Parent | 1,3-diacylglycerols |
---|
Alternative Parents | |
---|
Substituents | - 1,3-acyl-sn-glycerol
- Fatty acid ester
- Fatty acyl
- Dicarboxylic acid or derivatives
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular 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 |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
---|
Spectra |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - DG(18:1n9/0:0/18:1n9) GC-MS (1 TMS) - 70eV, Positive | splash10-00tr-9351102000-e3d6976a4eb65131936f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - DG(18:1n9/0:0/18:1n9) GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - DG(18:1n9/0:0/18:1n9) GC-MS ("DG(18:1n9/0:0/18:1n9),1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-11-02 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:1n9/0:0/18:1n9) 10V, Negative-QTOF | splash10-014i-1046009000-49c32aef4a0fca79c16c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:1n9/0:0/18:1n9) 20V, Negative-QTOF | splash10-02mr-3079002000-56f631186d8b17f3cbc9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:1n9/0:0/18:1n9) 40V, Negative-QTOF | splash10-001i-2092000000-2aaab2f3f640e2baac09 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:1n9/0:0/18:1n9) 10V, Positive-QTOF | splash10-00dr-2057229000-d19de0ed9adc16ccea02 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:1n9/0:0/18:1n9) 20V, Positive-QTOF | splash10-05tr-5359232000-bd0cd90772f66480e4f9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:1n9/0:0/18:1n9) 40V, Positive-QTOF | splash10-0a4i-7449100000-daa8d4c560dcdb9923ed | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum |
|
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | Not Available |
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| Not Available |
---|
Abnormal Concentrations |
---|
| Not Available |
---|
Predicted Concentrations |
---|
| |
Blood | 2.666 +/- 0.998 uM | Adult (>18 years old) | Both | Normal (Most Probable) | Calculated using MetaboAnalyst | Blood | 7.783 +/- 1.455 uM | Adult (>18 years old) | Both | Normal (Upper Limit) | Calculated using MetaboAnalyst |
|
---|
Associated Disorders and Diseases |
---|
Disease References | None |
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | Not Available |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 5497165 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 75735 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | Not Available |
---|
Good Scents ID | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
|
---|