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Record Information |
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Version | 4.0 |
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Status | Detected but not Quantified |
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Creation Date | 2008-09-12 01:14:10 UTC |
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Update Date | 2020-02-26 21:27:07 UTC |
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HMDB ID | HMDB0007079 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | DG(15:0/20:1(11Z)/0:0) |
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Description | DG(15:0/20:1(11Z)/0:0) 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 both the C-1 and C-2 positions. DG(15:0/20:1(11Z)/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of eicosenoic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the eicosenoic acid moiety is derived from vegetable oils and cod oils. 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-2 position. |
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Structure | |
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Synonyms | Value | Source |
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1-Pentadecanoyl-2-eicosenoyl-sn-glycerol | HMDB | DG(35:1) | HMDB | DAG(35:1) | HMDB | Diacylglycerol(35:1) | HMDB | Diglyceride | HMDB | Diacylglycerol(15:0/20:1) | HMDB | DAG(15:0/20:1) | HMDB | Diacylglycerol | HMDB | DG(15:0/20:1) | HMDB | 1-Pentadecanoyl-2-(11-eicosenoyl)-sn-glycerol | HMDB | DG(15:0/20:1(11Z)/0:0) | Lipid Annotator |
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Chemical Formula | C38H72O5 |
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Average Molecular Weight | 608.9753 |
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Monoisotopic Molecular Weight | 608.537975414 |
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IUPAC Name | (2S)-1-hydroxy-3-(pentadecanoyloxy)propan-2-yl (11Z)-icos-11-enoate |
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Traditional Name | diacylglycerol |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](CO)(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCCCC |
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InChI Identifier | InChI=1S/C38H72O5/c1-3-5-7-9-11-13-15-17-18-19-20-21-23-25-27-29-31-33-38(41)43-36(34-39)35-42-37(40)32-30-28-26-24-22-16-14-12-10-8-6-4-2/h17-18,36,39H,3-16,19-35H2,1-2H3/b18-17-/t36-/m0/s1 |
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InChI Key | DICYCLUXEYFAQX-ORMHLZIJSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerolipids |
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Sub Class | Diradylglycerols |
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Direct Parent | 1,2-diacylglycerols |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0fxt-4961346000-0cbbb2b3f62744ba7a88 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0000009000-8cfdee1586e79af1e938 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014n-0099063000-668ffefe3ae6df211278 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-016t-0099017000-43a99ed50df6099020b4 | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Inflammatory bowel disease | | details |
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Predicted Concentrations |
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Blood | 0.002 +/- 0.001 uM | Adult (>18 years old) | Both | Normal (Most Probable) | Calculated using MetaboAnalyst | Blood | 0.200 uM | Adult (>18 years old) | Both | Normal (Upper Limit) | Calculated using MetaboAnalyst |
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Associated Disorders and Diseases |
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Disease References | Inflammatory bowel disease |
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- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 53478008 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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