1.0 2011-09-21 00:28:06 UTC 2015-07-21 06:57:38 UTC FDB023323 D-Urobilinogen Urobilinogen is a colourless product of bilirubin reduction. It is formed in the intestines by bacterial action. Some urobilinogen is reabsorbed, taken up by the hepatocytes into the circulation and excreted by the kidney. This constitutes the normal "intrahepatic urobilinogen cycle". Increased amounts of bilirubin are formed in haemolysis which generates increased urobilinogen in the gut. In liver disease (such as hepatitis) the intrahepatic urobilinogen cycle is inhibited also increasing urobilinogen levels. Urobilinogen is converted to the yellow pigmented urobilin apparent in urine. The urobilinogen remaining in the intestine (stercobilinogen) is oxidized to brown stercobilin which gives the feces their characteristic color. In biliary obstruction, below normal amounts of conjugated bilirubin reach the intestine for conversion to urobilinogen. With limited urobilinogen available for reabsorption and excretion, the amount of urobilin found in the urine is low. [HMDB] D-Urobilinogen Urobilinogen C33H42N4O6 590.7098 590.310435096 3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(3-ethyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid 3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-1,2-dihydropyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(3-ethyl-4-methyl-5-oxo-1,2-dihydropyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid 17208-65-0 CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(CC3NC(=O)C(C=C)=C3C)N2)N1 InChI=1S/C33H42N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h8,26-27,34-35H,2,7,9-15H2,1,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41) KSQFFJKKJAEKTB-UHFFFAOYSA-N belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Bilirubins Organic compounds Organoheterocyclic compounds Tetrapyrroles and derivatives Bilirubins Aromatic heteromonocyclic compounds Azacyclic compounds Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Heteroaromatic compounds Hydrocarbon derivatives Lactams Organic oxides Organonitrogen compounds Organopnictogen compounds Pyrrolines Secondary carboxylic acid amides Substituted pyrroles Aromatic heteromonocyclic compound Azacycle Bilirubin skeleton Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Heteroaromatic compound Hydrocarbon derivative Lactam Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyrrole Pyrroline Secondary carboxylic acid amide Substituted pyrrole biladienes Solid logp 2.77 ALOGPS logs -4.46 ALOGPS solubility 2.05e-02 g/l ALOGPS logp 3.46 ChemAxon pka_strongest_acidic 4.06 ChemAxon pka_strongest_basic -0.038 ChemAxon iupac 3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(3-ethyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid ChemAxon average_mass 590.7098 ChemAxon mono_mass 590.310435096 ChemAxon smiles CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(CC3NC(=O)C(C=C)=C3C)N2)N1 ChemAxon formula C33H42N4O6 ChemAxon inchi InChI=1S/C33H42N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h8,26-27,34-35H,2,7,9-15H2,1,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41) ChemAxon inchikey KSQFFJKKJAEKTB-UHFFFAOYSA-N ChemAxon polar_surface_area 164.38 ChemAxon refractivity 166.09 ChemAxon polarizability 65.82 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Porphyrin Metabolism SMP00024 map00860 Specdb::CMs 17684 Specdb::CMs 38724 Specdb::MsMs 28445 Specdb::MsMs 28446 Specdb::MsMs 28447 Specdb::MsMs 35003 Specdb::MsMs 35004 Specdb::MsMs 35005 Specdb::MsMs 452026 Specdb::MsMs 2664469 Specdb::MsMs 2664470 Specdb::MsMs 2664471 Specdb::MsMs 3017805 Specdb::MsMs 3017806 Specdb::MsMs 3017807 Specdb::NmrOneD 258648 Specdb::NmrOneD 258649 Specdb::NmrOneD 258650 Specdb::NmrOneD 258651 Specdb::NmrOneD 258652 Specdb::NmrOneD 258653 Specdb::NmrOneD 258654 Specdb::NmrOneD 258655 Specdb::NmrOneD 258656 Specdb::NmrOneD 258657 Specdb::NmrOneD 258658 Specdb::NmrOneD 258659 Specdb::NmrOneD 258660 Specdb::NmrOneD 258661 Specdb::NmrOneD 258662 Specdb::NmrOneD 258663 Specdb::NmrOneD 258664 Specdb::NmrOneD 258665 Specdb::NmrOneD 258666 Specdb::NmrOneD 258667 HMDB04158 #<Reference:0x000055ce31981890> 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