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 22:01:06 UTC |
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Update Date | 2022-03-07 02:55:05 UTC |
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HMDB ID | HMDB0036839 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (ent-15beta)-15-Hydroxy-19-trachylobanoic acid |
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Description | (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 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 (ent-15beta)-15-Hydroxy-19-trachylobanoic acid. |
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Structure | CC12C3CC4(CCC5C(C)(CCCC5(C)C(O)=O)C4CC13)C2O InChI=1S/C20H30O3/c1-17-6-4-7-18(2,16(22)23)13(17)5-8-20-10-12-11(9-14(17)20)19(12,3)15(20)21/h11-15,21H,4-10H2,1-3H3,(H,22,23) |
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Synonyms | Value | Source |
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(ent-15b)-15-Hydroxy-19-trachylobanoate | Generator | (ent-15b)-15-Hydroxy-19-trachylobanoic acid | Generator | (ent-15beta)-15-Hydroxy-19-trachylobanoate | Generator | (ent-15Β)-15-hydroxy-19-trachylobanoate | Generator | (ent-15Β)-15-hydroxy-19-trachylobanoic acid | Generator | 16-Hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylate | Generator |
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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 | 16-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid |
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Traditional Name | 16-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid |
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CAS Registry Number | 83404-76-6 |
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SMILES | CC12C3CC4(CCC5C(C)(CCCC5(C)C(O)=O)C4CC13)C2O |
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InChI Identifier | InChI=1S/C20H30O3/c1-17-6-4-7-18(2,16(22)23)13(17)5-8-20-10-12-11(9-14(17)20)19(12,3)15(20)21/h11-15,21H,4-10H2,1-3H3,(H,22,23) |
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InChI Key | MHVNHDYWKUKRRJ-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 | |
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Substituents | - Atisane diterpenoid
- Kaurane diterpenoid
- Villanovane, atisane, trachylobane or helvifulvane diterpenoid
- Alkaloid or derivatives
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- 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 | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 265 - 267 °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 | | 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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(ent-15beta)-15-Hydroxy-19-trachylobanoic acid,1TMS,isomer #1 | CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C1CCC13CC4C(CC21)C4(C)C3O | 2603.1 | Semi standard non polar | 33892256 | (ent-15beta)-15-Hydroxy-19-trachylobanoic acid,1TMS,isomer #2 | CC1(C(=O)O)CCCC2(C)C1CCC13CC4C(CC21)C4(C)C3O[Si](C)(C)C | 2706.4 | Semi standard non polar | 33892256 | (ent-15beta)-15-Hydroxy-19-trachylobanoic acid,2TMS,isomer #1 | CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C1CCC13CC4C(CC21)C4(C)C3O[Si](C)(C)C | 2534.6 | Semi standard non polar | 33892256 | (ent-15beta)-15-Hydroxy-19-trachylobanoic acid,1TBDMS,isomer #1 | CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C1CCC13CC4C(CC21)C4(C)C3O | 2881.8 | Semi standard non polar | 33892256 | (ent-15beta)-15-Hydroxy-19-trachylobanoic acid,1TBDMS,isomer #2 | CC1(C(=O)O)CCCC2(C)C1CCC13CC4C(CC21)C4(C)C3O[Si](C)(C)C(C)(C)C | 2952.1 | Semi standard non polar | 33892256 | (ent-15beta)-15-Hydroxy-19-trachylobanoic acid,2TBDMS,isomer #1 | CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C1CCC13CC4C(CC21)C4(C)C3O[Si](C)(C)C(C)(C)C | 3047.5 | 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 - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-5394000000-337b088c7f7925f09afc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid GC-MS (2 TMS) - 70eV, Positive | splash10-006t-9036600000-cf300ccc616e3c8efc26 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 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 - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 10V, Positive-QTOF | splash10-0uxr-0049000000-61f9f606707e152dff0e | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 20V, Positive-QTOF | splash10-0zgi-0295000000-c3f9644e7a9625bc3396 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 40V, Positive-QTOF | splash10-0aor-5970000000-092246a2ed6e70b95e1d | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 10V, Negative-QTOF | splash10-014i-0069000000-99df82d2accafd9a25bc | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 20V, Negative-QTOF | splash10-06dj-0093000000-347444462e602f772ad5 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 40V, Negative-QTOF | splash10-0a4i-1091000000-783cd1b640f4e40d1765 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 10V, Negative-QTOF | splash10-014i-0009000000-062ad2a35e11d303cf23 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 20V, Negative-QTOF | splash10-014i-0009000000-062ad2a35e11d303cf23 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 40V, Negative-QTOF | splash10-014i-1009000000-ccc99b100decfcf42277 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 10V, Positive-QTOF | splash10-01b9-0098000000-acc22a07ab5e6edf097e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 20V, Positive-QTOF | splash10-01di-0093000000-8efb5bd4f03a205c7835 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-15beta)-15-Hydroxy-19-trachylobanoic acid 40V, Positive-QTOF | splash10-0a4i-7960000000-c6b172908bef2f473a18 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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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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Abnormal Concentrations |
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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 | FDB021672 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 35014269 |
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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 | 131752061 |
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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 ]
- (). 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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