| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-03-17 23:26:13 UTC |
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| Update date | 2019-11-26 03:20:41 UTC |
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| Primary ID | FDB021671 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Kaurenoic acid |
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| Description | Kaurenoic acid, also known as kaur-16-en-18-oic acid or kaurenoate, 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. Kaurenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Kaurenoic acid can be found in sunflower, which makes kaurenoic acid a potential biomarker for the consumption of this food product. |
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| CAS Number | 6730-83-2 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C20H30O2 |
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| IUPAC name | 5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid |
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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) |
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| InChI Key | NIKHGUQULKYIGE-UHFFFAOYSA-N |
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| Isomeric SMILES | CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3)C(O)=O |
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| Average Molecular Weight | 302.451 |
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| Monoisotopic Molecular Weight | 302.224580204 |
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| Classification |
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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 | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Kaurenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00ri-0390000000-2d35434664ad835a2ef9 | Spectrum | | Predicted GC-MS | Kaurenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Kaurenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Kaurenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Kaurenoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udr-0096000000-7f9038e4c1bf589f909b | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4r-0291000000-283ba5a9e04421592523 | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014r-4970000000-4fb81048c244660a4124 | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0049000000-c76464aa0ddcf412fdd8 | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0pb9-0094000000-49d912d0b06756cbaccd | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052o-0090000000-619c75dd5a7b5fe256f5 | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0pb9-0095000000-c1e4b304133d29afa12c | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0pvi-0392000000-dded88183d0b426edc9f | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kr-2910000000-82a99d67c952ebd533a4 | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0009000000-16d58525184e918518fa | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0009000000-16d58525184e918518fa | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-2039000000-dbbba85020ea7ca040a5 | 2021-10-12 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | Not Available |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | Not Available |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | JFQ29-S:KFS37-O |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | (-)-ENT-KAUR-16-EN-19-OIC-ACID |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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