1.0 2010-04-08 22:11:32 UTC 2025-11-19 00:50:40 UTC FDB014907 Limonexic acid Constituent of Citrus subspecies Limonexic acid is found in sweet orange and citrus. Limonexin Shihulimonin A C26H30O10 502.5104 502.18389718 19-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione 19-(2-hydroxy-5-oxo-2H-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione 99026-99-0 CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=CC(=O)OC1O InChI=1S/C26H30O10/c1-22(2)13-8-14(27)24(4)12(25(13)10-32-16(28)9-15(25)35-22)5-6-23(3)18(11-7-17(29)33-20(11)30)34-21(31)19-26(23,24)36-19/h7,12-13,15,18-20,30H,5-6,8-10H2,1-4H3 RTPPVNISJHFPFX-UHFFFAOYSA-N belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Limonoids Organic compounds Lipids and lipid-like molecules Prenol lipids Triterpenoids Aliphatic heteropolycyclic compounds 1,4-dioxepanes 11-oxosteroids Butenolides Delta valerolactones Dialkyl ethers Enoate esters Epoxides Hemiacetals Hydrocarbon derivatives Ketones Naphthalenes Naphthopyrans Organic oxides Oxacyclic compounds Oxanes Pyrans Steroid lactones Tetrahydrofurans Tricarboxylic acids and derivatives 1,4-dioxepane 11-oxosteroid 2-furanone 2-oxosteroid Aliphatic heteropolycyclic compound Alpha,beta-unsaturated carboxylic ester Carbonyl group Carboxylic acid derivative Carboxylic acid ester Delta valerolactone Delta_valerolactone Dialkyl ether Dihydrofuran Dioxepane Enoate ester Ether Hemiacetal Hydrocarbon derivative Ketone Lactone Limonoid skeleton Naphthalene Naphthopyran Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Oxirane Oxosteroid Pyran Steroid Steroid lactone Tetrahydrofuran Tricarboxylic acid or derivatives logp 1.83 ALOGPS logs -3.57 ALOGPS solubility 1.37e-01 g/l ALOGPS melting_point Mp 285-286° dec. logp 1.25 ChemAxon pka_strongest_acidic 5.3 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac 19-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione ChemAxon average_mass 502.5104 ChemAxon mono_mass 502.18389718 ChemAxon smiles CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=CC(=O)OC1O ChemAxon formula C26H30O10 ChemAxon inchi InChI=1S/C26H30O10/c1-22(2)13-8-14(27)24(4)12(25(13)10-32-16(28)9-15(25)35-22)5-6-23(3)18(11-7-17(29)33-20(11)30)34-21(31)19-26(23,24)36-19/h7,12-13,15,18-20,30H,5-6,8-10H2,1-4H3 ChemAxon inchikey RTPPVNISJHFPFX-UHFFFAOYSA-N ChemAxon polar_surface_area 137.96 ChemAxon refractivity 117.67 ChemAxon polarizability 49.48 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 7 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 19402 Specdb::CMs 44713 Specdb::MsMs 103647 Specdb::MsMs 103648 Specdb::MsMs 103649 Specdb::MsMs 169746 Specdb::MsMs 169747 Specdb::MsMs 169748 Specdb::MsMs 2712641 Specdb::MsMs 2712642 Specdb::MsMs 2712643 Specdb::MsMs 2965464 Specdb::MsMs 2965465 Specdb::MsMs 2965466 HMDB36075 #<Reference:0x000055ce307acdb8> Citrus Unknown generic Sweet orange Type 1 specific Citrus sinensis 2711