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 21:56:06 UTC |
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Update Date | 2022-03-07 02:55:03 UTC |
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HMDB ID | HMDB0036761 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 7,18-Dihydroxykaurenolide |
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Description | 7,18-Dihydroxykaurenolide belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 7,18-Dihydroxykaurenolide is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC12CCCC3(CO)C1C(OC3=O)C(O)C13CC(CCC21)C(=C)C3 InChI=1S/C20H28O4/c1-11-8-20-9-12(11)4-5-13(20)18(2)6-3-7-19(10-21)15(18)14(16(20)22)24-17(19)23/h12-16,21-22H,1,3-10H2,2H3 |
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Synonyms | Value | Source |
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7beta,18-Dihydroxykaurenolide | HMDB | ent-7a,18-Dihydroxy-16-kauren-19,6b-olide | HMDB |
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Chemical Formula | C20H28O4 |
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Average Molecular Weight | 332.4339 |
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Monoisotopic Molecular Weight | 332.198759384 |
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IUPAC Name | 9-hydroxy-13-(hydroxymethyl)-1-methyl-6-methylidene-11-oxapentacyclo[8.6.1.1⁵,⁸.0²,⁸.0¹³,¹⁷]octadecan-12-one |
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Traditional Name | 9-hydroxy-13-(hydroxymethyl)-1-methyl-6-methylidene-11-oxapentacyclo[8.6.1.1⁵,⁸.0²,⁸.0¹³,¹⁷]octadecan-12-one |
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CAS Registry Number | 7758-47-6 |
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SMILES | CC12CCCC3(CO)C1C(OC3=O)C(O)C13CC(CCC21)C(=C)C3 |
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InChI Identifier | InChI=1S/C20H28O4/c1-11-8-20-9-12(11)4-5-13(20)18(2)6-3-7-19(10-21)15(18)14(16(20)22)24-17(19)23/h12-16,21-22H,1,3-10H2,2H3 |
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InChI Key | RDUNXXWNAKBVER-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. |
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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 | Terpene lactones |
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Direct Parent | Diterpene lactones |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aliphatic heteropolycyclic 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 | 215 - 217 °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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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7,18-Dihydroxykaurenolide,1TMS,isomer #1 | C=C1CC23CC1CCC2C1(C)CCCC2(CO[Si](C)(C)C)C(=O)OC(C21)C3O | 2743.2 | Semi standard non polar | 33892256 | 7,18-Dihydroxykaurenolide,1TMS,isomer #2 | C=C1CC23CC1CCC2C1(C)CCCC2(CO)C(=O)OC(C21)C3O[Si](C)(C)C | 2732.7 | Semi standard non polar | 33892256 | 7,18-Dihydroxykaurenolide,2TMS,isomer #1 | C=C1CC23CC1CCC2C1(C)CCCC2(CO[Si](C)(C)C)C(=O)OC(C21)C3O[Si](C)(C)C | 2758.2 | Semi standard non polar | 33892256 | 7,18-Dihydroxykaurenolide,1TBDMS,isomer #1 | C=C1CC23CC1CCC2C1(C)CCCC2(CO[Si](C)(C)C(C)(C)C)C(=O)OC(C21)C3O | 3036.1 | Semi standard non polar | 33892256 | 7,18-Dihydroxykaurenolide,1TBDMS,isomer #2 | C=C1CC23CC1CCC2C1(C)CCCC2(CO)C(=O)OC(C21)C3O[Si](C)(C)C(C)(C)C | 2981.0 | Semi standard non polar | 33892256 | 7,18-Dihydroxykaurenolide,2TBDMS,isomer #1 | C=C1CC23CC1CCC2C1(C)CCCC2(CO[Si](C)(C)C(C)(C)C)C(=O)OC(C21)C3O[Si](C)(C)C(C)(C)C | 3267.3 | Semi standard non polar | 33892256 |
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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 - 7,18-Dihydroxykaurenolide GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-0935000000-f317179e4544589bd7e4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 7,18-Dihydroxykaurenolide GC-MS (2 TMS) - 70eV, Positive | splash10-0229-4361900000-5c2f58bef333616e6152 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 7,18-Dihydroxykaurenolide 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 - 7,18-Dihydroxykaurenolide 10V, Positive-QTOF | splash10-0159-0019000000-59fd99e9649356b71cac | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 20V, Positive-QTOF | splash10-014i-0459000000-f608335d3702dae32ab8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 40V, Positive-QTOF | splash10-014l-4891000000-aeb00047f00d90752e3e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 10V, Negative-QTOF | splash10-001i-0019000000-a2625dde60e5a56cd00b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 20V, Negative-QTOF | splash10-0lzi-0089000000-20b3b32ca85b67014f36 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 40V, Negative-QTOF | splash10-0a4r-0090000000-4757313d2f4d8b8f4fa3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 10V, Negative-QTOF | splash10-001i-0009000000-bd69facddc36af19b908 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 20V, Negative-QTOF | splash10-001i-0097000000-b88ace95a4232db1bf14 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 40V, Negative-QTOF | splash10-001i-0097000000-a01ad5fab860f74d9b9a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 10V, Positive-QTOF | splash10-001i-0009000000-e2fa0bbe5e36e88183dd | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 20V, Positive-QTOF | splash10-001r-0039000000-9ea056e515814b5b0921 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7,18-Dihydroxykaurenolide 40V, Positive-QTOF | splash10-007n-0948000000-90d1d790c06bfb351def | 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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