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 21:56:03 UTC |
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Update Date | 2022-03-07 02:55:03 UTC |
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HMDB ID | HMDB0036760 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid |
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Description | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid, also known as 1,2-bis(4-methoxyphenyl)-1,3-butanediol, 9CI, 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 small amount of articles have been published on (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid. |
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Structure | CC1(CCCC2(C)C1CCC13CC(CC=C21)C(O)(CO)C3)C(O)=O InChI=1S/C20H30O4/c1-17-7-3-8-18(2,16(22)23)14(17)6-9-19-10-13(4-5-15(17)19)20(24,11-19)12-21/h5,13-14,21,24H,3-4,6-12H2,1-2H3,(H,22,23) |
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Synonyms | Value | Source |
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(ent-16BetaOH)-16,17-dihydroxy-9(11)-kauren-19-Oate | Generator | 1,2-Bis(4-methoxyphenyl)-1,3-butanediol, 9ci | HMDB | 14-Hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-10-ene-5-carboxylate | HMDB |
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Chemical Formula | C20H30O4 |
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Average Molecular Weight | 334.4498 |
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Monoisotopic Molecular Weight | 334.214409448 |
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IUPAC Name | 14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-10-ene-5-carboxylic acid |
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Traditional Name | 14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-10-ene-5-carboxylic acid |
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CAS Registry Number | 55483-24-4 |
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SMILES | CC1(CCCC2(C)C1CCC13CC(CC=C21)C(O)(CO)C3)C(O)=O |
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InChI Identifier | InChI=1S/C20H30O4/c1-17-7-3-8-18(2,16(22)23)14(17)6-9-19-10-13(4-5-15(17)19)20(24,11-19)12-21/h5,13-14,21,24H,3-4,6-12H2,1-2H3,(H,22,23) |
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InChI Key | QSJIZGQGHYROGD-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 | - Kaurane diterpenoid
- Tertiary alcohol
- Cyclic alcohol
- 1,2-diol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- 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 | |
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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 | 184 - 185 °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-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,1TMS,isomer #1 | CC1(C(=O)O)CCCC2(C)C3=CCC4CC3(CCC12)CC4(CO)O[Si](C)(C)C | 2923.4 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,1TMS,isomer #2 | CC1(C(=O)O)CCCC2(C)C3=CCC4CC3(CCC12)CC4(O)CO[Si](C)(C)C | 2933.5 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,1TMS,isomer #3 | CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C3=CCC4CC3(CCC12)CC4(O)CO | 2833.7 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,2TMS,isomer #1 | CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C3=CCC4CC3(CCC12)CC4(CO)O[Si](C)(C)C | 2793.5 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,2TMS,isomer #2 | CC1(C(=O)O)CCCC2(C)C3=CCC4CC3(CCC12)CC4(CO[Si](C)(C)C)O[Si](C)(C)C | 2898.3 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,2TMS,isomer #3 | CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C3=CCC4CC3(CCC12)CC4(O)CO[Si](C)(C)C | 2799.6 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,3TMS,isomer #1 | CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C3=CCC4CC3(CCC12)CC4(CO[Si](C)(C)C)O[Si](C)(C)C | 2787.0 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,1TBDMS,isomer #1 | CC1(C(=O)O)CCCC2(C)C3=CCC4CC3(CCC12)CC4(CO)O[Si](C)(C)C(C)(C)C | 3176.3 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,1TBDMS,isomer #2 | CC1(C(=O)O)CCCC2(C)C3=CCC4CC3(CCC12)CC4(O)CO[Si](C)(C)C(C)(C)C | 3190.2 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,1TBDMS,isomer #3 | CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C3=CCC4CC3(CCC12)CC4(O)CO | 3110.0 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,2TBDMS,isomer #1 | CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C3=CCC4CC3(CCC12)CC4(CO)O[Si](C)(C)C(C)(C)C | 3298.9 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,2TBDMS,isomer #2 | CC1(C(=O)O)CCCC2(C)C3=CCC4CC3(CCC12)CC4(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3398.5 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,2TBDMS,isomer #3 | CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C3=CCC4CC3(CCC12)CC4(O)CO[Si](C)(C)C(C)(C)C | 3302.0 | Semi standard non polar | 33892256 | (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid,3TBDMS,isomer #1 | CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C3=CCC4CC3(CCC12)CC4(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3511.3 | 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 - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0cdi-2398000000-db160aa52fa0588c28b1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid GC-MS (3 TMS) - 70eV, Positive | splash10-000i-3004490000-bc6803d30a9f1ac81b7b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-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-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 10V, Positive-QTOF | splash10-000i-0049000000-1d19bb5fd019b04d0f85 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 20V, Positive-QTOF | splash10-01bj-0294000000-50cf9b6744e26de796ab | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 40V, Positive-QTOF | splash10-00xr-4691000000-3be672e5dc86cf8aeb71 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 10V, Negative-QTOF | splash10-001i-0039000000-7370478cb2b6bf551259 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 20V, Negative-QTOF | splash10-0ka9-0096000000-3c3d8ac7ddd3d2f1e42f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 40V, Negative-QTOF | splash10-0a4i-0092000000-d96aa01fdbc3ca860b8d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 10V, Negative-QTOF | splash10-001i-0009000000-fd5cd126f4d2eefd9030 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 20V, Negative-QTOF | splash10-001i-0009000000-ff6b61413fede893ddef | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 40V, Negative-QTOF | splash10-001i-1049000000-49d590eef34f9c62c1e9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 10V, Positive-QTOF | splash10-000i-0095000000-f5ab328850da8c4c2683 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 20V, Positive-QTOF | splash10-01w0-0191000000-2129098f456d4a9d68cc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid 40V, Positive-QTOF | splash10-0a5i-2930000000-20e0bac61dc8d2f5d5d4 | 2021-09-23 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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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 | FDB015701 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 35014237 |
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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 | 74029190 |
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PDB ID | Not Available |
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ChEBI ID | 191672 |
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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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