Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-23 19:31:38 UTC |
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Update Date | 2021-09-23 19:31:38 UTC |
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HMDB ID | HMDB0302664 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | (-)-Kaur-16-en-19-oic acid |
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Description | (-)-kaur-16-en-19-oic acid, also known as ent-kaurenoic acid or ent-kaur-16-en-19-oate, is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids 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 (-)-kaur-16-en-19-oic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (-)-kaur-16-en-19-oic acid can be found in sugar apple and sunflower, which makes (-)-kaur-16-en-19-oic acid a potential biomarker for the consumption of these food products. |
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Structure | [H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CCC[C@@]21C)C(O)=O InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15+,16+,18-,19-,20-/m1/s1 |
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Synonyms | Value | Source |
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(-)-Kaur-16-en-19-Oic acid | ChEBI | (5beta,8alpha,9beta,10alpha,13alpha)-Kaur-16-en-18-Oic acid | ChEBI | ent-Kaur-16(17)-en-19-Oic acid | ChEBI | ent-Kaurenoic acid | ChEBI | Kaur-16-en-18-Oic acid | ChEBI | Kauren-19-Oic acid | ChEBI | Kaurenic acid | ChEBI | Kaurenoic acid | ChEBI | ent-Kaur-16-en-19-Oate | Kegg | (-)-Kaur-16-en-19-Oate | Generator | (5b,8a,9b,10a,13a)-Kaur-16-en-18-Oate | Generator | (5b,8a,9b,10a,13a)-Kaur-16-en-18-Oic acid | Generator | (5beta,8alpha,9beta,10alpha,13alpha)-Kaur-16-en-18-Oate | Generator | (5Β,8α,9β,10α,13α)-kaur-16-en-18-Oate | Generator | (5Β,8α,9β,10α,13α)-kaur-16-en-18-Oic acid | Generator | ent-Kaur-16(17)-en-19-Oate | Generator | ent-Kaurenoate | Generator | Kaur-16-en-18-Oate | Generator | Kauren-19-Oate | Generator | Kaurenate | Generator | Kaurenoate | Generator | ent-Kaur-16-en-18-Oic acid | MeSH | 3beta-Hydroxy-kaurenoic acid | MeSH | ent-Kaur-16-en-19-Oic acid | KEGG |
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Chemical Formula | C20H30O2 |
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Average Molecular Weight | 302.458 |
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Monoisotopic Molecular Weight | 302.224580206 |
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IUPAC Name | (1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid |
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Traditional Name | (1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CCC[C@@]21C)C(O)=O |
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InChI Identifier | InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15+,16+,18-,19-,20-/m1/s1 |
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InChI Key | NIKHGUQULKYIGE-OTCXFQBHSA-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
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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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 | |
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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 | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available | Show more...
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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 - (-)-Kaur-16-en-19-oic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2022-08-08 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | Not Available | 2022-08-06 | Not Available | 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 - (-)-Kaur-16-en-19-oic acid 10V, Positive-QTOF | splash10-0udi-0189000000-e32ee1de5a9c608c2a44 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 20V, Positive-QTOF | splash10-0a4r-0391000000-e394ed814c12150daac8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 40V, Positive-QTOF | splash10-00kr-4980000000-a62048379e0c65cfa374 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 10V, Negative-QTOF | splash10-0udi-0049000000-7e4d4b429d5eff18ab7e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 20V, Negative-QTOF | splash10-0pb9-0094000000-8f1bdf9553eed92d0c8c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 40V, Negative-QTOF | splash10-052o-1090000000-0d495a6257dc2d019e9c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 10V, Positive-QTOF | splash10-0zfr-0089000000-c65698a8dba37e012d50 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 20V, Positive-QTOF | splash10-0zmr-0943000000-2ffd59d91ab4e2b79ac4 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 40V, Positive-QTOF | splash10-014u-9720000000-930c6014a094be91c659 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 10V, Negative-QTOF | splash10-0udi-0009000000-16d58525184e918518fa | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 20V, Negative-QTOF | splash10-0udi-0009000000-16d58525184e918518fa | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-Kaur-16-en-19-oic acid 40V, Negative-QTOF | splash10-0udj-0097000000-208d1681517a7ae9b6f9 | 2021-10-21 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-18 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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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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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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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 | FDB005672 |
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KNApSAcK ID | C00000881 |
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Chemspider ID | 21258059 |
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KEGG Compound ID | C11874 |
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BioCyc ID | CPD1F-132 |
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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 | Not Available |
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PDB ID | Not Available |
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ChEBI ID | 15417 |
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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 | rw1893841 |
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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 | Not Available |
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