1.0 2020-04-02 17:47:17 UTC 2025-11-19 03:07:48 UTC FDB097307 Limonin (17-beta-D-glucoside-) C56H100O6 869.41 868.75199094 (1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid (1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-furan-3-yl({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC InChI=1S/C56H100O6/c1-4-7-10-13-16-19-22-24-26-27-28-30-31-34-37-40-43-46-49-55(58)61-52-53(51-60-54(57)48-45-42-39-36-33-21-18-15-12-9-6-3)62-56(59)50-47-44-41-38-35-32-29-25-23-20-17-14-11-8-5-2/h8,11,15,17-18,20,25,29,53H,4-7,9-10,12-14,16,19,21-24,26-28,30-52H2,1-3H3/b11-8-,18-15-,20-17-,29-25-/t53-/m0/s1 YCBCZIKALKDHRL-ZLSCYYNLSA-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 Aromatic heteropolycyclic compounds Acetals Carboxylic acid esters Carboxylic acids Delta valerolactones Dialkyl ethers Dicarboxylic acids and derivatives Furans Heteroaromatic compounds Hexoses Hydrocarbon derivatives Ketones O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Oxirane carboxylic acids Polyols Primary alcohols Secondary alcohols Tetrahydrofurans Acetal Alcohol Aromatic heteropolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Delta valerolactone Delta_valerolactone Dialkyl ether Dicarboxylic acid or derivatives Ether Furan Glycosyl compound Heteroaromatic compound Hexose monosaccharide Hydrocarbon derivative Ketone Lactone Limonoid skeleton Monosaccharide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Oxirane Oxirane carboxylic acid Oxirane carboxylic acid or derivatives Polyol Primary alcohol Secondary alcohol Tetrahydrofuran Limonoids beta-D-glucoside logp 1.07 ALOGPS logs -2.81 ALOGPS solubility 1.01e+00 g/l ALOGPS logp 0.022 ChemAxon pka_strongest_acidic 3.97 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac (1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid ChemAxon average_mass 869.41 ChemAxon mono_mass 868.75199094 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC ChemAxon formula C56H100O6 ChemAxon inchi InChI=1S/C56H100O6/c1-4-7-10-13-16-19-22-24-26-27-28-30-31-34-37-40-43-46-49-55(58)61-52-53(51-60-54(57)48-45-42-39-36-33-21-18-15-12-9-6-3)62-56(59)50-47-44-41-38-35-32-29-25-23-20-17-14-11-8-5-2/h8,11,15,17-18,20,25,29,53H,4-7,9-10,12-14,16,19,21-24,26-28,30-52H2,1-3H3/b11-8-,18-15-,20-17-,29-25-/t53-/m0/s1 ChemAxon inchikey YCBCZIKALKDHRL-ZLSCYYNLSA-N ChemAxon polar_surface_area 214.95 ChemAxon refractivity 150.62 ChemAxon polarizability 64.26 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 240928 Specdb::MsMs 240929 Specdb::MsMs 240930 Specdb::MsMs 242983 Specdb::MsMs 242984 Specdb::MsMs 242985 Specdb::MsMs 3610027 Specdb::MsMs 3610028 Specdb::MsMs 3610029 Specdb::MsMs 3610030 Specdb::MsMs 3610031 Specdb::MsMs 3610032 Grapefruit Type 1 specific Citrus X paradisi 37656 Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 Milk (Cow) Type 2 specific 10.671667 32.0 0.23 uM Sweet orange Type 1 specific Citrus sinensis 2711