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 18:07:07 UTC |
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Update Date | 2022-03-07 02:53:41 UTC |
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HMDB ID | HMDB0033400 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Annoglabasin A |
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Description | Annoglabasin A 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. Annoglabasin A is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | COC(=O)C1(CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3)OC(C)=O InChI=1S/C23H34O5/c1-15(25)28-23(19(26)27-4)13-22-11-8-17-20(2,14-24)9-5-10-21(17,3)18(22)7-6-16(23)12-22/h14,16-18H,5-13H2,1-4H3 |
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Synonyms | Value | Source |
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Methyl ent-16a-acetoxy-19-oxo-17-kauranoate | HMDB | Methyl 14-(acetyloxy)-5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylic acid | Generator |
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Chemical Formula | C23H34O5 |
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Average Molecular Weight | 390.5131 |
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Monoisotopic Molecular Weight | 390.240624198 |
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IUPAC Name | methyl 14-(acetyloxy)-5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylate |
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Traditional Name | methyl 14-(acetyloxy)-5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylate |
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CAS Registry Number | 205312-85-2 |
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SMILES | COC(=O)C1(CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3)OC(C)=O |
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InChI Identifier | InChI=1S/C23H34O5/c1-15(25)28-23(19(26)27-4)13-22-11-8-17-20(2,14-24)9-5-10-21(17,3)18(22)7-6-16(23)12-22/h14,16-18H,5-13H2,1-4H3 |
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InChI Key | GBAYHCBQSSWKTG-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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Physiological effect | Not Available |
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Disposition | |
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Process | |
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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 | 138 - 140 °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 - Annoglabasin A GC-MS (Non-derivatized) - 70eV, Positive | splash10-0535-3098000000-37d3409c9c9e398a6c33 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annoglabasin A 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 - Annoglabasin A 10V, Positive-QTOF | splash10-0006-0019000000-350bfe7878f2b82daec0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 20V, Positive-QTOF | splash10-000w-1159000000-beed1fb8e851b80dfae6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 40V, Positive-QTOF | splash10-059f-2692000000-74e0363e88e1fe8354cc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 10V, Negative-QTOF | splash10-000i-1009000000-8a0195cd11b6875c2e39 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 20V, Negative-QTOF | splash10-0a4s-4019000000-e768cb1bcdedf3684fa8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 40V, Negative-QTOF | splash10-0a4r-9031000000-a17f52a873e831848248 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 10V, Positive-QTOF | splash10-0nmi-0009000000-9fd5e90654ef0152d4fb | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 20V, Positive-QTOF | splash10-114i-0849000000-31b33e4479cf41b0aa14 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 40V, Positive-QTOF | splash10-06yd-3941000000-099162ac37757ed447af | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 10V, Negative-QTOF | splash10-000i-0009000000-4387b01c6ff0b13fcaea | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 20V, Negative-QTOF | splash10-0adi-5059000000-71a6aac12ba7bc286b2f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annoglabasin A 40V, Negative-QTOF | splash10-0a4i-9020000000-7a6e2a9a0597e52aca95 | 2021-09-25 | 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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