1.0 2011-09-21 01:24:50 UTC 2015-07-21 06:59:07 UTC FDB027468 Acetaminophen glucuronide Acetaminophen glucuronide is a natural human metabolite of Acetaminophen generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. [HMDB] 4-(acetylamino)phenyl beta-D-glucopyranosiduronic acid 4-(acetylamino)phenyl beta-delta-glucopyranosiduronic acid 4-acetamidophenol glucuronide 4-acetamidophenyl b-D-glucopyranosiduronic acid 4-acetamidophenyl b-delta-glucopyranosiduronic acid 4-acetamidophenyl beta-D-glucopyranosiduronic acid 4-acetamidophenyl beta-delta-glucopyranosiduronic acid P-Acetamidophenyl β-D-glucuronide paracetamol glucuronide C14H17NO8 327.2867 327.095416525 (2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid acetaminophen glucuronide 16110-10-4 CC(=O)NC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1 InChI=1S/C14H17NO8/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21)/t9-,10-,11+,12-,14+/m0/s1 IPROLSVTVHAQLE-BYNIDDHOSA-N belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Phenolic glycosides Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aromatic heteromonocyclic compounds Acetals Beta hydroxy acids and derivatives Carbonyl compounds Carboximidic acids Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Monosaccharides O-glucuronides O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Phenol ethers Phenoxy compounds Polyols Propargyl-type 1,3-dipolar organic compounds Pyrans Secondary alcohols 1-o-glucuronide Acetal Alcohol Aromatic heteromonocyclic compound Benzenoid Beta-hydroxy acid Carbonyl group Carboximidic acid Carboximidic acid derivative Carboxylic acid Carboxylic acid derivative Glucuronic acid or derivatives Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives Monocyclic benzene moiety Monosaccharide O-glucuronide O-glycosyl compound Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Phenol ether Phenolic glycoside Phenoxy compound Polyol Propargyl-type 1,3-dipolar organic compound Pyran Secondary alcohol beta-D-glucosiduronic acid Solid logp -0.68 ALOGPS logs -1.07 ALOGPS solubility 2.77e+01 g/l ALOGPS logp -1 ChemAxon pka_strongest_acidic 3.17 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid ChemAxon average_mass 327.2867 ChemAxon mono_mass 327.095416525 ChemAxon smiles CC(=O)NC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1 ChemAxon formula C14H17NO8 ChemAxon inchi InChI=1S/C14H17NO8/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21)/t9-,10-,11+,12-,14+/m0/s1 ChemAxon inchikey IPROLSVTVHAQLE-BYNIDDHOSA-N ChemAxon polar_surface_area 145.55 ChemAxon refractivity 74.91 ChemAxon polarizability 30.69 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21028 Specdb::CMs 30468 Specdb::CMs 39441 Specdb::CMs 99948 Specdb::CMs 130709 Specdb::CMs 138443 Specdb::MsMs 102993 Specdb::MsMs 102994 Specdb::MsMs 102995 Specdb::MsMs 168912 Specdb::MsMs 168913 Specdb::MsMs 168914 Specdb::MsMs 439970 Specdb::MsMs 450263 Specdb::MsMs 450264 Specdb::MsMs 2237914 Specdb::MsMs 2239641 Specdb::MsMs 2244233 Specdb::MsMs 2244825 Specdb::MsMs 2245314 Specdb::MsMs 2245854 Specdb::MsMs 2246345 Specdb::MsMs 2246915 Specdb::MsMs 2247346 Specdb::MsMs 2247956 Specdb::MsMs 2248307 Specdb::MsMs 2249066 Specdb::MsMs 2249350 Specdb::MsMs 2250059 Specdb::MsMs 2250368 Specdb::MsMs 2252032 Specdb::NmrOneD 92232 Specdb::NmrOneD 92233 Specdb::NmrOneD 92234 Specdb::NmrOneD 92235 Specdb::NmrOneD 92236 Specdb::NmrOneD 92237 Specdb::NmrOneD 92238 Specdb::NmrOneD 92239 Specdb::NmrOneD 92240 Specdb::NmrOneD 92241 Specdb::NmrOneD 92242 Specdb::NmrOneD 92243 Specdb::NmrOneD 92244 Specdb::NmrOneD 92245 Specdb::NmrOneD 92246 Specdb::NmrOneD 92247 Specdb::NmrOneD 92248 Specdb::NmrOneD 92249 Specdb::NmrOneD 92250 Specdb::NmrOneD 92251 HMDB10316 32636 #<Reference:0x000055ce3214e190> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Beta-glucuronidase P08236 GUSB UDP-glucuronosyltransferase 1-1 P22309 UGT1A1 UDP-glucuronosyltransferase 1-4 P22310 UGT1A4 UDP-glucuronosyltransferase 1-6 P19224 UGT1A6 UDP-glucuronosyltransferase 1-9 O60656 UGT1A9 UDP-glucuronosyltransferase 2B4 P06133 UGT2B4 UDP-glucuronosyltransferase 2B7 P16662 UGT2B7