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 21:53:42 UTC |
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Update Date | 2022-03-07 02:55:02 UTC |
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HMDB ID | HMDB0036725 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | ent-17-Oxo-15-kauren-19-oic acid |
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Description | ent-17-Oxo-15-kauren-19-oic 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. ent-17-Oxo-15-kauren-19-oic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC12CCCC(C)(C1CCC13CC(CCC21)C(C=O)=C3)C(O)=O InChI=1S/C20H28O3/c1-18-7-3-8-19(2,17(22)23)15(18)6-9-20-10-13(4-5-16(18)20)14(11-20)12-21/h11-13,15-16H,3-10H2,1-2H3,(H,22,23) |
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Synonyms | Value | Source |
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ent-17-oxo-15-Kauren-19-Oate | Generator | 14-Formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylate | Generator |
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Chemical Formula | C20H28O3 |
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Average Molecular Weight | 316.4345 |
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Monoisotopic Molecular Weight | 316.203844762 |
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IUPAC Name | 14-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid |
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Traditional Name | 14-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid |
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CAS Registry Number | 77887-58-2 |
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SMILES | CC12CCCC(C)(C1CCC13CC(CCC21)C(C=O)=C3)C(O)=O |
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InChI Identifier | InChI=1S/C20H28O3/c1-18-7-3-8-19(2,17(22)23)15(18)6-9-20-10-13(4-5-16(18)20)14(11-20)12-21/h11-13,15-16H,3-10H2,1-2H3,(H,22,23) |
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InChI Key | DIURMAFIAYOVGU-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 | 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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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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-17-Oxo-15-kauren-19-oic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0uei-0391000000-9f5662fe055af96d3c0e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00di-5298000000-ed82181793c5a887758b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - ent-17-Oxo-15-kauren-19-oic 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-17-Oxo-15-kauren-19-oic acid 10V, Positive-QTOF | splash10-014i-0197000000-d7d8c1f0876a89d1fcd4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 20V, Positive-QTOF | splash10-00xs-0291000000-8a1e428e84fb7a5db71e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 40V, Positive-QTOF | splash10-0fvl-3691000000-b9dbc7d0d75f456cf8c0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 10V, Negative-QTOF | splash10-014i-0049000000-525410a8e3d3ac56c297 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 20V, Negative-QTOF | splash10-00xr-0094000000-2e311ddb2e99e0b75f9f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 40V, Negative-QTOF | splash10-0597-1090000000-cb22c4c564128858033e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 10V, Negative-QTOF | splash10-014i-0009000000-d337ec43015bf5d00be6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 20V, Negative-QTOF | splash10-014i-0029000000-b0acbb4d62e0cc1b7d69 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 40V, Negative-QTOF | splash10-014i-2095000000-5beeae7ffd887102a862 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 10V, Positive-QTOF | splash10-00di-0092000000-efd3617b3566b35162ff | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 20V, Positive-QTOF | splash10-010r-0391000000-c4c88ca77bcfe07ec2b6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - ent-17-Oxo-15-kauren-19-oic acid 40V, Positive-QTOF | splash10-0ldi-2972000000-6636db821ebcfe5fb350 | 2021-09-24 | 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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