1.0 2011-09-21 00:28:07 UTC 2015-07-21 06:57:38 UTC FDB023324 L-Urobilin L-Urobilin or Stercobilin is a byproduct of bilirubin degradation. It is a tetrapyrrole chemical compound, responsible for the typical brown color of human feces. It is created by bacterial action on bilirubin and subsequent oxidation. In plasma virtually all the bilirubin is tightly bound to plasma proteins, largely albumin, because it is only sparingly soluble in aqueous solutions at physiological pH. In the sinusoids unconjugated bilirubin dissocates from albumin, enters the liver cells across the cell membrane through non-ionic diffusion to the smooth endoplasmatic reticulum, where it is converted to a water-soluble ester glucuronide by bilirubin UDP-glucuronyl transferase. Following conjugation, bilirubin is transferred rapidly across the canalicular membrane into the bile canaliculi. In the intestinal tract bilirubin is reduced to urobilinogen, which is subsequently reabsorbed to some extent into the enterohepatic circulation, removed from plasma by the liver and excreted unchanged in the bile. The residual part of urobilinogen is further reduced to urobilin, stercobilin and dipyrrolmethenes and excreted in the feces. [HMDB] L-Stercobilin Stercobilin Urobilin C33H46N4O6 594.7415 594.341735224 3-(2-{[3-(2-carboxyethyl)-5-[(3-ethyl-5-hydroxy-4-methyl-3,4-dihydro-2H-pyrrol-2-yl)methyl]-4-methyl-2H-pyrrol-2-ylidene]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-methylpyrrol-2-ylidene]methyl}-5-[(4-ethyl-5-hydroxy-3-methyl-3,4-dihydro-2H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid 34217-90-8 CCC1C(CC2=NC(=CC3=C(CCC(O)=O)C(C)=C(CC4NC(=O)C(CC)C4C)N3)C(CCC(O)=O)=C2C)NC(=O)C1C InChI=1S/C33H46N4O6/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/h15-16,19-21,26-27,34H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41) TYOWQSLRVAUSMI-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 Dipyrrins Heteroaromatic compounds Hydrocarbon derivatives Ketimines Lactams Organic oxides Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Pyrrolidine-2-ones Secondary carboxylic acid amides 2-pyrrolidone Aromatic heteromonocyclic compound Azacycle Bilirubin skeleton Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Dipyrrin Heteroaromatic compound Hydrocarbon derivative Imine Ketimine Lactam Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound Pyrrole Pyrrolidine Pyrrolidone Secondary carboxylic acid amide Substituted pyrrole Solid logp 3.21 ALOGPS logs -4.73 ALOGPS solubility 1.11e-02 g/l ALOGPS logp 2.2 ChemAxon pka_strongest_acidic 4.13 ChemAxon pka_strongest_basic 6.49 ChemAxon iupac 3-(2-{[3-(2-carboxyethyl)-5-[(3-ethyl-5-hydroxy-4-methyl-3,4-dihydro-2H-pyrrol-2-yl)methyl]-4-methyl-2H-pyrrol-2-ylidene]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 594.7415 ChemAxon mono_mass 594.341735224 ChemAxon smiles CCC1C(CC2=NC(=CC3=C(CCC(O)=O)C(C)=C(CC4NC(=O)C(CC)C4C)N3)C(CCC(O)=O)=C2C)NC(=O)C1C ChemAxon formula C33H46N4O6 ChemAxon inchi InChI=1S/C33H46N4O6/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/h15-16,19-21,26-27,34H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41) ChemAxon inchikey TYOWQSLRVAUSMI-UHFFFAOYSA-N ChemAxon polar_surface_area 167.93 ChemAxon refractivity 166.24 ChemAxon polarizability 68.08 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon HMDB04159 #<Reference:0x000055ce306068d8>