Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-22 15:33:38 UTC |
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Update Date | 2021-09-14 15:40:57 UTC |
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HMDB ID | HMDB0061114 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Atractyligenin |
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Description | Atractyligenin 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. Based on a literature review a significant number of articles have been published on Atractyligenin. |
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Structure | C[C@H]1C(=C)C2CC11CCC3[C@@H](C[C@@H](O)C[C@@]3(C)C1CC2)C(O)=O InChI=1S/C20H30O3/c1-11-12(2)20-7-6-16-15(18(22)23)8-14(21)10-19(16,3)17(20)5-4-13(11)9-20/h12-17,21H,1,4-10H2,2-3H3,(H,22,23)/t12-,13?,14+,15+,16?,17?,19+,20?/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C20H30O3 |
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Average Molecular Weight | 318.4504 |
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Monoisotopic Molecular Weight | 318.219494826 |
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IUPAC Name | (5R,7R,9R,15S)-7-hydroxy-9,15-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid |
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Traditional Name | (5R,7R,9R,15S)-7-hydroxy-9,15-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | C[C@H]1C(=C)C2CC11CCC3[C@@H](C[C@@H](O)C[C@@]3(C)C1CC2)C(O)=O |
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InChI Identifier | InChI=1S/C20H30O3/c1-11-12(2)20-7-6-16-15(18(22)23)8-14(21)10-19(16,3)17(20)5-4-13(11)9-20/h12-17,21H,1,4-10H2,2-3H3,(H,22,23)/t12-,13?,14+,15+,16?,17?,19+,20?/m0/s1 |
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InChI Key | DKWHHGKUVUGDBR-LREIXEELSA-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 | |
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Substituents | - Kaurane diterpenoid
- Cyclic alcohol
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homopolycyclic compound
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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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Atractyligenin,1TMS,isomer #1 | C=C1C2CCC3C(CCC4[C@H](C(=O)O)C[C@@H](O[Si](C)(C)C)C[C@]43C)(C2)[C@H]1C | 2707.2 | Semi standard non polar | 33892256 | Atractyligenin,1TMS,isomer #2 | C=C1C2CCC3C(CCC4[C@H](C(=O)O[Si](C)(C)C)C[C@@H](O)C[C@]43C)(C2)[C@H]1C | 2573.1 | Semi standard non polar | 33892256 | Atractyligenin,2TMS,isomer #1 | C=C1C2CCC3C(CCC4[C@H](C(=O)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@]43C)(C2)[C@H]1C | 2598.8 | Semi standard non polar | 33892256 | Atractyligenin,1TBDMS,isomer #1 | C=C1C2CCC3C(CCC4[C@H](C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]43C)(C2)[C@H]1C | 2949.0 | Semi standard non polar | 33892256 | Atractyligenin,1TBDMS,isomer #2 | C=C1C2CCC3C(CCC4[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@]43C)(C2)[C@H]1C | 2823.1 | Semi standard non polar | 33892256 | Atractyligenin,2TBDMS,isomer #1 | C=C1C2CCC3C(CCC4[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]43C)(C2)[C@H]1C | 3075.3 | 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 - Atractyligenin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-0192000000-c93a805a1cf1e53c4b50 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Atractyligenin GC-MS (2 TMS) - 70eV, Positive | splash10-0002-5126900000-26221ea29a313c31095d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Atractyligenin 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 - Atractyligenin 10V, Positive-QTOF | splash10-0uxr-0049000000-5e3504e5f452d0fd8b5e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 20V, Positive-QTOF | splash10-0zgi-0194000000-7c7a7920913840e33658 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 40V, Positive-QTOF | splash10-0udi-2590000000-1199e9bd6ba6e9ca4740 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 10V, Negative-QTOF | splash10-014i-0069000000-d4c633e1c17779518cda | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 20V, Negative-QTOF | splash10-0601-0093000000-b1dcb2dabb7ee7e78f9f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 40V, Negative-QTOF | splash10-0a4i-2091000000-bc83e171c3d3cf1cdf9d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 10V, Negative-QTOF | splash10-014i-0009000000-062ad2a35e11d303cf23 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 20V, Negative-QTOF | splash10-014i-0039000000-3ae3cc49c6d2f3a258de | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 40V, Negative-QTOF | splash10-014i-2049000000-c097bb7477be55c213a7 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 10V, Positive-QTOF | splash10-014i-0009000000-b251663f66d06178e9ca | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 20V, Positive-QTOF | splash10-0gb9-0294000000-a185e7a647359ea37c3d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Atractyligenin 40V, Positive-QTOF | splash10-0zfs-4961000000-6c9118625fc79165d931 | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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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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| Not Available |
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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 | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 35031849 |
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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 | 131770032 |
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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 | 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 | - 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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