Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 21:26:45 UTC |
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Update Date | 2022-03-07 02:54:52 UTC |
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HMDB ID | HMDB0036315 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dimethyl ent-16alpha-kaurane-17,19-dioate |
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Description | Dimethyl ent-16alpha-kaurane-17,19-dioate belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Dimethyl ent-16alpha-kaurane-17,19-dioate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | COC(=O)C1CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(=O)OC InChI=1S/C22H34O4/c1-20-9-5-10-21(2,19(24)26-4)16(20)8-11-22-12-14(6-7-17(20)22)15(13-22)18(23)25-3/h14-17H,5-13H2,1-4H3 |
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Synonyms | Value | Source |
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Dimethyl ent-16a-kaurane-17,19-dioate | Generator | Dimethyl ent-16a-kaurane-17,19-dioic acid | Generator | Dimethyl ent-16alpha-kaurane-17,19-dioic acid | Generator | Dimethyl ent-16α-kaurane-17,19-dioate | Generator | Dimethyl ent-16α-kaurane-17,19-dioic acid | Generator | 5,14-Dimethyl 5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,14-dicarboxylic acid | Generator |
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Chemical Formula | C22H34O4 |
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Average Molecular Weight | 362.503 |
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Monoisotopic Molecular Weight | 362.245709576 |
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IUPAC Name | 5,14-dimethyl 5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,14-dicarboxylate |
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Traditional Name | 5,14-dimethyl 5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,14-dicarboxylate |
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CAS Registry Number | Not Available |
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SMILES | COC(=O)C1CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(=O)OC |
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InChI Identifier | InChI=1S/C22H34O4/c1-20-9-5-10-21(2,19(24)26-4)16(20)8-11-22-12-14(6-7-17(20)22)15(13-22)18(23)25-3/h14-17H,5-13H2,1-4H3 |
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InChI Key | USASLHCCADYMNF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Diterpenoids |
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Direct Parent | Kaurane diterpenoids |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Not Available | Not Available |
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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 | 165 - 166 °C | 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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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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 - Dimethyl ent-16alpha-kaurane-17,19-dioate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ugj-0369000000-617e87531b3418b9971f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | 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 - Dimethyl ent-16alpha-kaurane-17,19-dioate 10V, Positive-QTOF | splash10-03e9-0009000000-12e64ea9c1fdffecf145 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 20V, Positive-QTOF | splash10-0gx0-0229000000-ab45a56de228c0d9f8b3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 40V, Positive-QTOF | splash10-006x-0291000000-3ef051b11d8fbd1720a4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 10V, Negative-QTOF | splash10-03di-0009000000-301bc8093aad403f77d9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 20V, Negative-QTOF | splash10-03di-0019000000-8f61217c9f00cc3f2bcb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 40V, Negative-QTOF | splash10-00kb-2098000000-30fb29e6546517573507 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 10V, Negative-QTOF | splash10-03di-0009000000-d67feeb1f80dc228b73b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 20V, Negative-QTOF | splash10-03di-0009000000-7af1566facff01863663 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 40V, Negative-QTOF | splash10-0r01-0059000000-28ebc3eefeedc1a0ee30 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 10V, Positive-QTOF | splash10-0w90-0049000000-74e821a9c48feabe432f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 20V, Positive-QTOF | splash10-0303-1976000000-04882e183e2cc242356c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl ent-16alpha-kaurane-17,19-dioate 40V, Positive-QTOF | splash10-000i-0912000000-b1f1d249e886fb293436 | 2021-09-23 | Wishart Lab | View Spectrum |
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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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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