1.0 2011-03-17 23:26:13 UTC 2025-11-19 02:38:59 UTC FDB021671 Kaurenoic acid 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. (-)-16-Kauren-19-oic acid Cunabic acid ent-16-Kauren-19-oic acid ent-Kaurenoic acid Kaurenoic acid C20H30O2 302.451 302.224580204 5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid 5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid 6730-83-2 CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3)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) NIKHGUQULKYIGE-UHFFFAOYSA-N 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. Kaurane diterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Diterpenoids Aliphatic homopolycyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Kaurane diterpenoid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound logp 4.13 ALOGPS logs -5.80 ALOGPS solubility 4.78e-04 g/l ALOGPS melting_point Mp 179-181? logp 4.81 ChemAxon pka_strongest_acidic 4.84 ChemAxon iupac 5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid ChemAxon average_mass 302.451 ChemAxon mono_mass 302.224580204 ChemAxon smiles CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3)C(O)=O ChemAxon formula C20H30O2 ChemAxon inchi 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) ChemAxon inchikey NIKHGUQULKYIGE-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 87.36 ChemAxon polarizability 35.26 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 104914 Specdb::CMs 116942 Specdb::CMs 119795 Specdb::CMs 130210 Specdb::CMs 829331 Specdb::MsMs 1326670 Specdb::MsMs 1326671 Specdb::MsMs 1326672 Specdb::MsMs 1441015 Specdb::MsMs 1441016 Specdb::MsMs 1441017 Specdb::MsMs 3409622 Specdb::MsMs 3409623 Specdb::MsMs 3409624 Specdb::MsMs 3409625 Specdb::MsMs 3409626 Specdb::MsMs 3409627 Sunflower Type 1 specific Helianthus annuus 4232