1.0 2016-09-30 23:08:18 UTC 2020-04-22 15:13:26 UTC BMDB0004159 BMDB04159 L-Urobilin L-Stercobilin Stercobilin Urobilin Stercobilin III alpha 3-(2-{[(2E)-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)propanoate C33H46N4O6 594.7415 594.341735224 3-[(2E)-2-{[3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxopyrrolidin-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methylidene}-5-[(3-ethyl-4-methyl-5-oxopyrrolidin-2-yl)methyl]-4-methyl-2H-pyrrol-3-yl]propanoic acid stercobilin CCC1C(CC2=N\C(=C\C3=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)/b29-15+ TYOWQSLRVAUSMI-WKULSOCRSA-N belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Organic compounds Organoheterocyclic compounds Tetrapyrroles and derivatives Bilirubins Bilirubins 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 Aromatic heteromonocyclic compounds Solid melting_point 236 °C logp 2.97 ALOGPS logs -4.73 ALOGPS logp 1.38 ChemAxon pka_strongest_acidic 3.87 ChemAxon pka_strongest_basic 6.07 ChemAxon iupac 3-[(2E)-2-{[3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxopyrrolidin-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methylidene}-5-[(3-ethyl-4-methyl-5-oxopyrrolidin-2-yl)methyl]-4-methyl-2H-pyrrol-3-yl]propanoic acid ChemAxon average_mass 594.7415 ChemAxon mono_mass 594.341735224 ChemAxon smiles CCC1C(CC2=N\C(=C\C3=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)/b29-15+ ChemAxon inchikey TYOWQSLRVAUSMI-WKULSOCRSA-N ChemAxon polar_surface_area 160.95 ChemAxon refractivity 165.2 ChemAxon polarizability 67.98 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 18161 Specdb::MsMs 47967 Specdb::MsMs 47968 Specdb::MsMs 47969 Specdb::MsMs 144417 Specdb::MsMs 144418 Specdb::MsMs 144419 Specdb::NmrOneD 306231 Specdb::NmrOneD 306232 Specdb::NmrOneD 306233 Specdb::NmrOneD 306234 Specdb::NmrOneD 306235 Specdb::NmrOneD 306236 Specdb::NmrOneD 306237 Specdb::NmrOneD 306238 Specdb::NmrOneD 306239 Specdb::NmrOneD 306240 Specdb::NmrOneD 306241 Specdb::NmrOneD 306242 Specdb::NmrOneD 306243 Specdb::NmrOneD 306244 Specdb::NmrOneD 306245 Specdb::NmrOneD 306246 Specdb::NmrOneD 306247 Specdb::NmrOneD 306248 Specdb::NmrOneD 306249 Specdb::NmrOneD 306250 5280818 Urobilin Fischer, Hans. The Bilo Pigments. I. Z. physiol. Chem. (1912), 73 204-39. CAN 6:565 AN 1912:565