1.0 2011-09-21 00:18:33 UTC 2015-07-21 06:57:20 UTC FDB022727 Mesobilirubinogen 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. At times, it is re-excreted in the urine, where it may be later oxidized to urobilin. (PMID: 16504607) [HMDB] 2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate 2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid 2,17-diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-Biline-8,12-dipropionic acid 8,12-Bis(2-carboxyethyl)-3,18-diethyl-2,7,13,17-tetramethylbilane-1,19(4H,16H)-dione i-Urobilinogen Mesobilirubinogen ixalpha Urobilinogen ixalpha C33H44N4O6 592.7257 592.32608516 3-(2-{[3-(2-carboxyethyl)-5-[(4-ethyl-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 urobilinogen 14684-37-8 CCC1=C(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/C33H44N4O6/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/h26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41) OBHRVMZSZIDDEK-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 bilanes Solid logp 3.11 ALOGPS logs -4.53 ALOGPS solubility 1.74e-02 g/l ALOGPS logp 3.77 ChemAxon pka_strongest_acidic 4.06 ChemAxon pka_strongest_basic -0.018 ChemAxon iupac 3-(2-{[3-(2-carboxyethyl)-5-[(4-ethyl-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 592.7257 ChemAxon mono_mass 592.32608516 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(CC)=C3C)N2)N1 ChemAxon formula C33H44N4O6 ChemAxon inchi InChI=1S/C33H44N4O6/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/h26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41) ChemAxon inchikey OBHRVMZSZIDDEK-UHFFFAOYSA-N ChemAxon polar_surface_area 164.38 ChemAxon refractivity 166.04 ChemAxon polarizability 67.38 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 296355 Specdb::NmrOneD 296356 Specdb::NmrOneD 296357 Specdb::NmrOneD 296358 Specdb::NmrOneD 296359 Specdb::NmrOneD 296360 Specdb::NmrOneD 296361 Specdb::NmrOneD 296362 Specdb::NmrOneD 296363 Specdb::NmrOneD 296364 Specdb::NmrOneD 296365 Specdb::NmrOneD 296366 Specdb::NmrOneD 296367 Specdb::NmrOneD 296368 Specdb::NmrOneD 296369 Specdb::NmrOneD 296370 Specdb::NmrOneD 296371 Specdb::NmrOneD 296372 Specdb::NmrOneD 296373 Specdb::NmrOneD 296374 Specdb::MsMs 290059 Specdb::MsMs 290060 Specdb::MsMs 290061 Specdb::MsMs 329662 Specdb::MsMs 329663 Specdb::MsMs 329664 Specdb::MsMs 438663 Specdb::MsMs 3061175 Specdb::MsMs 3061176 Specdb::MsMs 3061177 Specdb::MsMs 3109101 Specdb::MsMs 3109102 Specdb::MsMs 3109103 Specdb::CMs 10927 Specdb::CMs 38176 Specdb::CMs 282915 Specdb::CMs 424529 Specdb::CMs 424530 Specdb::CMs 424531 Specdb::CMs 424532 Specdb::CMs 424533 Specdb::CMs 424534 Specdb::CMs 424535 Specdb::CMs 424536 Specdb::CMs 424537 Specdb::CMs 424538 Specdb::CMs 424539 Specdb::CMs 424540 Specdb::CMs 424541 Specdb::CMs 424542 Specdb::CMs 424543 Specdb::CMs 424544 Specdb::CMs 424545 Specdb::CMs 424546 Specdb::CMs 424547 Specdb::CMs 424548 Specdb::CMs 424549 Specdb::CMs 424550 HMDB01898 #<Reference:0x000055ce307ac200> 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