1.0 2010-04-08 22:06:31 UTC 2025-11-18 22:58:10 UTC FDB005061 Obacunone 17-O-beta-D-glucoside Obacunone 17-o-beta-d-glucoside is a member of the class of compounds known as limonoids. Limonoids 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. Obacunone 17-o-beta-d-glucoside is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Obacunone 17-o-beta-d-glucoside can be found in lemon, mandarin orange (clementine, tangerine), and sweet orange, which makes obacunone 17-o-beta-d-glucoside a potential biomarker for the consumption of these food products. C32H42O13 634.6681 634.26254143 9-[furan-3-yl({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-5,5a,6,7,7a,9,10,11,11a,11b-decahydro-3H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid 9-[furan-3-yl({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-6,10,11,11a-tetrahydro-5aH-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid CC1(CCC2C3(C)C=CC(=O)OC(C)(C)C3CC(=O)C2(C)C11OC1C(O)=O)C(OC1OC(CO)C(O)C(O)C1O)C1=COC=C1 InChI=1S/C32H42O13/c1-28(2)18-12-19(34)31(5)17(29(18,3)9-7-20(35)44-28)6-10-30(4,32(31)25(45-32)26(39)40)24(15-8-11-41-14-15)43-27-23(38)22(37)21(36)16(13-33)42-27/h7-9,11,14,16-18,21-25,27,33,36-38H,6,10,12-13H2,1-5H3,(H,39,40) MXZVBPOYCKIXHN-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 Aromatic heteropolycyclic compounds Acetals Carboxylic acids Dialkyl ethers Dicarboxylic acids and derivatives Enoate esters Furans Heteroaromatic compounds Hexoses Hydrocarbon derivatives Ketones Lactones O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Oxirane carboxylic acids Polyols Primary alcohols Secondary alcohols Acetal Alcohol Alpha,beta-unsaturated carboxylic ester Aromatic heteropolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Dialkyl ether Dicarboxylic acid or derivatives Enoate ester 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 logp 1.62 ALOGPS logs -3.42 ALOGPS solubility 2.40e-01 g/l ALOGPS logp 1.45 ChemAxon pka_strongest_acidic 4.04 ChemAxon pka_strongest_basic -3 ChemAxon iupac 9-[furan-3-yl({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-5,5a,6,7,7a,9,10,11,11a,11b-decahydro-3H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid ChemAxon average_mass 634.6681 ChemAxon mono_mass 634.26254143 ChemAxon smiles CC1(CCC2C3(C)C=CC(=O)OC(C)(C)C3CC(=O)C2(C)C11OC1C(O)=O)C(OC1OC(CO)C(O)C(O)C1O)C1=COC=C1 ChemAxon formula C32H42O13 ChemAxon inchi InChI=1S/C32H42O13/c1-28(2)18-12-19(34)31(5)17(29(18,3)9-7-20(35)44-28)6-10-30(4,32(31)25(45-32)26(39)40)24(15-8-11-41-14-15)43-27-23(38)22(37)21(36)16(13-33)42-27/h7-9,11,14,16-18,21-25,27,33,36-38H,6,10,12-13H2,1-5H3,(H,39,40) ChemAxon inchikey MXZVBPOYCKIXHN-UHFFFAOYSA-N ChemAxon polar_surface_area 205.72 ChemAxon refractivity 152.09 ChemAxon polarizability 63.57 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 11 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 96090 Specdb::MsMs 96091 Specdb::MsMs 96092 Specdb::MsMs 160503 Specdb::MsMs 160504 Specdb::MsMs 160505 Specdb::MsMs 3601322 Specdb::MsMs 3601323 Specdb::MsMs 3601324 Specdb::MsMs 3601325 Specdb::MsMs 3601326 Specdb::MsMs 3601327 Lemon Type 1 specific Citrus limon 2708 Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 Sweet orange Type 1 specific Citrus sinensis 2711