Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-09-12 01:17:15 UTC |
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Update Date | 2022-03-07 02:49:41 UTC |
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HMDB ID | HMDB0007263 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) |
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Description | DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/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(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of adrenic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the adrenic acid moiety is derived from animal fats. 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 | [H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C43H72O5/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(46)48-41(39-44)40-47-42(45)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-23,26,28,41,44H,3-10,15-16,20,24-25,27,29-40H2,1-2H3/b13-11-,14-12-,19-17-,22-21-,23-18-,28-26-/t41-/m0/s1 |
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Synonyms | Value | Source |
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1-Linoleoyl-2-adrenoyl-sn-glycerol | HMDB | DAG(18:2/22:4) | HMDB | DAG(18:2N6/22:4N6) | HMDB | DAG(18:2W6/22:4W6) | HMDB | DAG(40:6) | HMDB | DG(18:2/22:4) | HMDB | DG(18:2N6/22:4N6) | HMDB | DG(18:2W6/22:4W6) | HMDB | DG(40:6) | HMDB | Diacylglycerol | HMDB | Diacylglycerol(18:2/22:4) | HMDB | Diacylglycerol(18:2n6/22:4n6) | HMDB | Diacylglycerol(18:2W6/22:4W6) | HMDB | Diacylglycerol(40:6) | HMDB | Diglyceride | HMDB | 1-(9Z,12Z-Octadecadienoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerol | HMDB | DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) | Lipid Annotator |
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Chemical Formula | C43H72O5 |
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Average Molecular Weight | 669.0288 |
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Monoisotopic Molecular Weight | 668.537975414 |
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IUPAC Name | (2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoate |
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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)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C43H72O5/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(46)48-41(39-44)40-47-42(45)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-23,26,28,41,44H,3-10,15-16,20,24-25,27,29-40H2,1-2H3/b13-11-,14-12-,19-17-,22-21-,23-18-,28-26-/t41-/m0/s1 |
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InChI Key | REWOPMLGNOGDCI-IUTJGAPQSA-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 | |
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Disposition | |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0014470)
- Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0015310)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/18:2(9Z,12Z)) (PathBank: SMP0024328)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0024329)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0024330)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:2(13Z,16Z)) (PathBank: SMP0024331)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0024332)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0024333)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0024334)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0024335)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0024336)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0024337)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0024338)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0024339)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/20:2(11Z,14Z)) (PathBank: SMP0033287)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0033288)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:0) (PathBank: SMP0066840)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z)) (PathBank: SMP0066841)
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) | [H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 4952.1 | Standard polar | 33892256 | DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) | [H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 4307.8 | Standard non polar | 33892256 | DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) | [H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 4832.9 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) GC-MS (Non-derivatized) - 70eV, Positive | splash10-01p9-1296033000-3ac47e97b83e4b1ced2b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 10V, Positive-QTOF | splash10-014r-1049004000-69e88c226b4581f57deb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 20V, Positive-QTOF | splash10-02g9-2098031000-463928e03cdfe4b74975 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 40V, Positive-QTOF | splash10-00ri-1092030000-2aa3514206cd69c4cf6c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 10V, Negative-QTOF | splash10-040r-0096003000-d3d9fd0d9300fb80d0f2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 20V, Negative-QTOF | splash10-01t9-1093000000-e6d7446760d428feb96e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 40V, Negative-QTOF | splash10-03gi-4095000000-5f035f28cd9807de8ea0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 10V, Negative-QTOF | splash10-014i-1047009000-08cda64530360e2b16d1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 20V, Negative-QTOF | splash10-0200-6097001000-31c6f7c6ea448e5f9df3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 40V, Negative-QTOF | splash10-06w9-6196000000-de1e95182e12940ff4d6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 10V, Positive-QTOF | splash10-014i-3129046000-ebcabde4c1f09cc4242e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 20V, Positive-QTOF | splash10-0670-2249000000-c640c87b6533562dd92a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 40V, Positive-QTOF | splash10-00kr-1449100000-b3568968a2be23b01080 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 10V, Positive-QTOF | splash10-000i-0000009000-e2329eb25be3f42c3a5d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 20V, Positive-QTOF | splash10-000i-0009004000-8f85c25bd00937eb2ce0 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 40V, Positive-QTOF | splash10-000i-0009004000-21e4faf10fefcf3a55fa | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 10V, Positive-QTOF | splash10-0006-0000009000-d8fc180957e9e2b5f8d1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 20V, Positive-QTOF | splash10-0006-0000009000-d8fc180957e9e2b5f8d1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) 40V, Positive-QTOF | splash10-0bt9-0009601000-ff2f39827158b8213e71 | 2021-09-24 | Wishart Lab | View 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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Blood | Detected and Quantified | 0.254 +/- 0.032 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Not Specified | Premature neonates | | details |
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Predicted Concentrations |
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Blood | 0.003 +/- 0.003 uM | Adult (>18 years old) | Both | Normal (Most Probable) | Calculated using MetaboAnalyst | Blood | 0.067 +/- 0.058 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 | None |
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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 | FDB024456 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 7822829 |
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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 | 9543879 |
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PDB ID | Not Available |
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ChEBI ID | 89176 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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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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