1.0 2011-09-21 00:28:02 UTC 2025-11-19 02:43:46 UTC FDB023322 L-Urobilinogen Urobilinogen is an uribiniloid, the product of bilirubin reduction in multiple sequential reactions. Urobilinogens are colorless chromogens that may in turn be oxidized to respective yellow oxidation products, urobilins. Under normal conditions only small amounts of bilirubin can be found in stools of adults while urobilinoids are predominant bile pigments (50-250 mg/day). Only negligible amounts of fecal urobilinoids are present in the intestinal lumen of infants during the first months of their life, due to undeveloped intestinal microflora capable of reducing bilirubin. This presumably contributes importantly to the pathogenesis of neonatal jaundice. In adults, the urobilinoid production is highly efficient. (PMID: 16504607) [HMDB] (-)-2,17-diethyl-1,2,3,4,5,10,15,16,17,18,19,22,23,24-tetradecahydro-3,7,13,18-tetramethyl-1,19-dioxo-Biline-8,12-dipropionic acid (-)-Stercobilinogen L-Stercobilinogen Stercobilinogen Stercobilinogen ixalpha C33H48N4O6 596.7574 596.357385288 3-(2-{[3-(2-carboxyethyl)-5-[(3-ethyl-5-hydroxy-4-methyl-3,4-dihydro-2H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(4-ethyl-5-hydroxy-3-methyl-3,4-dihydro-2H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid 3-(2-{[3-(2-carboxyethyl)-5-[(3-ethyl-5-hydroxy-4-methyl-3,4-dihydro-2H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(4-ethyl-5-hydroxy-3-methyl-3,4-dihydro-2H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid 17095-63-5 CCC1C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(CC3NC(=O)C(CC)C3C)N2)N1 InChI=1S/C33H48N4O6/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/h16,19-21,26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41) VKGRRZVYCXLHII-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 Pyrrolidine-2-ones Secondary carboxylic acid amides Substituted pyrroles 2-pyrrolidone 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 Pyrrolidine Pyrrolidone Secondary carboxylic acid amide Substituted pyrrole bilanes Solid logp 3.03 ALOGPS logs -5.28 ALOGPS solubility 3.10e-03 g/l ALOGPS logp 4.36 ChemAxon pka_strongest_acidic 3.49 ChemAxon pka_strongest_basic 4.71 ChemAxon iupac 3-(2-{[3-(2-carboxyethyl)-5-[(3-ethyl-5-hydroxy-4-methyl-3,4-dihydro-2H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(4-ethyl-5-hydroxy-3-methyl-3,4-dihydro-2H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid ChemAxon average_mass 596.7574 ChemAxon mono_mass 596.357385288 ChemAxon smiles CCC1C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(CC3NC(=O)C(CC)C3C)N2)N1 ChemAxon formula C33H48N4O6 ChemAxon inchi InChI=1S/C33H48N4O6/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/h16,19-21,26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41) ChemAxon inchikey VKGRRZVYCXLHII-UHFFFAOYSA-N ChemAxon polar_surface_area 171.36 ChemAxon refractivity 166.02 ChemAxon polarizability 68.01 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 24756 Specdb::CMs 38723 Specdb::MsMs 320803 Specdb::MsMs 320804 Specdb::MsMs 320805 Specdb::MsMs 368272 Specdb::MsMs 368273 Specdb::MsMs 368274 HMDB04157 #<Reference:0x000055ce31dab3d0>