1.0 2016-09-30 22:31:28 UTC 2020-04-22 15:03:49 UTC BMDB0000488 BMDB00488 4E,15Z-Bilirubin IXa Bilirubin belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Bilirubin is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Bilirubin exists in all living species, ranging from bacteria to humans. In cattle, bilirubin is involved in the metabolic pathway called the porphyrin metabolism pathway. Bilirubin is a potentially toxic compound. (4E)2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo--21H-biline-8,12-dipropanoic acid (4E)2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo--21H-biline-8,12-dipropanoate (4E,15Z)-Bilirubin ixa (4E,15Z)-Bilirubin (4E,15Z)-Bilirubin IXalpha (4E,15Z)-Bilirubin IXα 4E,15Z-Bilirubin IXa 4E,15Z-Bilirubin IXalpha 4E,15Z-Bilirubin IXα C33H36N4O6 584.6621 584.263484904 3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid 3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2\NC(=O)C(C=C)=C2C)N1 InChI=1S/C33H36N4O6/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/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13+,27-14- BPYKTIZUTYGOLE-KDUUSRDASA-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 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 Aromatic heteromonocyclic compounds biladienes dicarboxylic acid Solid logp 3.22 ALOGPS logs -4.78 ALOGPS logp 3.12 ChemAxon pka_strongest_acidic 4.03 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac 3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid ChemAxon average_mass 584.6621 ChemAxon mono_mass 584.263484904 ChemAxon smiles CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2\NC(=O)C(C=C)=C2C)N1 ChemAxon formula C33H36N4O6 ChemAxon inchi InChI=1S/C33H36N4O6/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/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13+,27-14- ChemAxon inchikey BPYKTIZUTYGOLE-KDUUSRDASA-N ChemAxon polar_surface_area 164.38 ChemAxon refractivity 168.9 ChemAxon polarizability 65.37 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 6 ChemAxon donor_count 6 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::NmrTwoD 2001 Specdb::MsMs 1218101 Specdb::MsMs 1227070 Specdb::MsMs 1227071 Specdb::MsMs 1227072 Specdb::MsMs 1342666 Specdb::MsMs 1342667 Specdb::MsMs 1342668 Specdb::MsMs 3035390 Specdb::MsMs 3035391 Specdb::MsMs 3035392 Specdb::MsMs 3104873 Specdb::MsMs 3104874 Specdb::MsMs 3104875 Specdb::NmrOneD 5162 Specdb::NmrOneD 5163 Specdb::NmrOneD 5164 Specdb::NmrOneD 5165 Specdb::CMs 282734 Specdb::CMs 407505 Specdb::CMs 407506 Specdb::CMs 407507 Specdb::CMs 407508 Specdb::CMs 407509 Specdb::CMs 407510 Specdb::CMs 407511 Specdb::CMs 407512 Specdb::CMs 407513 Specdb::CMs 407514 Specdb::CMs 407515 Specdb::CMs 407516 Specdb::CMs 407517 Specdb::CMs 407518 Specdb::CMs 407519 Specdb::CMs 407520 Specdb::CMs 407521 Specdb::CMs 407522 Specdb::CMs 407523 Specdb::CMs 407524 Specdb::CMs 407525 Specdb::CMs 407526 Specdb::CMs 407527 Specdb::CMs 407528 FDB022070 13628097 C00029828 21252250 72719 Bilirubin McDonagh, Antony F.; Lightner, David A.; Wooldridge, Timothy A. Geometric isomerization of bilirubin-IXa and its dimethyl ester. Journal of the Chemical Society, Chemical Communications (1979), (3), 110-12.