1.0 2010-04-08 22:06:31 UTC 2025-11-18 22:58:09 UTC FDB005058 Nomilinic acid 17-O-beta-D-glucoside Nomilinic acid 17-o-beta-d-glucoside is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Nomilinic acid 17-o-beta-d-glucoside can be found in lemon, mandarin orange (clementine, tangerine), and sweet orange, which makes nomilinic acid 17-o-beta-d-glucoside a potential biomarker for the consumption of these food products. C34H48O16 712.742 712.294235466 (2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-1-(acetyloxy)-2-carboxyethyl]-2-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid (2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-1-(acetyloxy)-2-carboxyethyl]-2-[(R)-furan-3-yl({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid [H][C@](CC(O)=O)(OC(C)=O)[C@@]1(C)[C@@]([H])(CC(=O)[C@]2(C)[C@]1([H])CC[C@@](C)([C@@]([H])(O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)C1=COC=C1)C21O[C@]1([H])C(O)=O)C(C)(C)O InChI=1S/C34H48O16/c1-15(36)47-21(12-22(38)39)32(5)18-7-9-31(4,34(27(50-34)28(43)44)33(18,6)20(37)11-19(32)30(2,3)45)26(16-8-10-46-14-16)49-29-25(42)24(41)23(40)17(13-35)48-29/h8,10,14,17-19,21,23-27,29,35,40-42,45H,7,9,11-13H2,1-6H3,(H,38,39)(H,43,44)/t17-,18-,19+,21-,23-,24+,25-,26+,27-,29+,31+,32-,33+,34?/m1/s1 MUZNNCNJBAPYJF-UNWTYGGYSA-N belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. Saccharolipids Organic compounds Lipids and lipid-like molecules Saccharolipids Aromatic heteropolycyclic compounds Acetals Carbocyclic fatty acids Carboxylic acid esters Carboxylic acids Dialkyl ethers Furans Heteroaromatic compounds Hydrocarbon derivatives Hydroxy fatty acids Ketones Monosaccharides O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Oxirane carboxylic acids Polyols Primary alcohols Secondary alcohols Sesquiterpenoids Terpene glycosides Tertiary alcohols Tricarboxylic acids and derivatives Acetal Alcohol Aromatic heteropolycyclic compound Carbocyclic fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Dialkyl ether Ether Fatty acyl Furan Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydroxy fatty acid Ketone 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 Saccharolipid Secondary alcohol Sesquiterpenoid Terpene glycoside Tertiary alcohol Tricarboxylic acid or derivatives logp 1.12 ALOGPS logs -2.92 ALOGPS solubility 8.51e-01 g/l ALOGPS logp -0.082 ChemAxon pka_strongest_acidic 3.68 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac (2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-1-(acetyloxy)-2-carboxyethyl]-2-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid ChemAxon average_mass 712.742 ChemAxon mono_mass 712.294235466 ChemAxon smiles [H][C@](CC(O)=O)(OC(C)=O)[C@@]1(C)[C@@]([H])(CC(=O)[C@]2(C)[C@]1([H])CC[C@@](C)([C@@]([H])(O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)C1=COC=C1)C21O[C@]1([H])C(O)=O)C(C)(C)O ChemAxon formula C34H48O16 ChemAxon inchi InChI=1S/C34H48O16/c1-15(36)47-21(12-22(38)39)32(5)18-7-9-31(4,34(27(50-34)28(43)44)33(18,6)20(37)11-19(32)30(2,3)45)26(16-8-10-46-14-16)49-29-25(42)24(41)23(40)17(13-35)48-29/h8,10,14,17-19,21,23-27,29,35,40-42,45H,7,9,11-13H2,1-6H3,(H,38,39)(H,43,44)/t17-,18-,19+,21-,23-,24+,25-,26+,27-,29+,31+,32-,33+,34?/m1/s1 ChemAxon inchikey MUZNNCNJBAPYJF-UNWTYGGYSA-N ChemAxon polar_surface_area 263.25 ChemAxon refractivity 165 ChemAxon polarizability 69.67 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 14 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 79038 Specdb::MsMs 79039 Specdb::MsMs 79040 Specdb::MsMs 139536 Specdb::MsMs 139537 Specdb::MsMs 139538 Specdb::MsMs 3601316 Specdb::MsMs 3601317 Specdb::MsMs 3601318 Specdb::MsMs 3601319 Specdb::MsMs 3601320 Specdb::MsMs 3601321 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