2.0 2012-05-31 14:53:57 -0600 2015-06-03 17:20:24 -0600 ECMDB21000 M2MDB001421 D-Urobilinogen Urobilinogen is a colourless product of bilirubin reduction. It is formed in the intestines by bacterial action. Urobilinogen is an intermediate of porphyrin and chlorophyll metabolism. It is converted from bilirubin beta-diglucuronide by beta-D-glucuronidase (EC:3.2.1.31) and converts to D-urobilin. (KEGG). D-Urobilinogen Urobilinogen C33H42N4O6 590.7098 590.310435096 3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-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 3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-1,2-dihydropyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(3-ethyl-4-methyl-5-oxo-1,2-dihydropyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid 17208-65-0 CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(CC3NC(=O)C(C=C)=C3C)N2)N1 InChI=1S/C33H42N4O6/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/h8,26-27,34-35H,2,7,9-15H2,1,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41) KSQFFJKKJAEKTB-UHFFFAOYSA-N Solid Inner membrane Membrane Outer membrane logp 2.77 ALOGPS logs -4.46 ALOGPS solubility 2.05e-02 g/l ALOGPS logp 3.46 ChemAxon pka_strongest_acidic 4.06 ChemAxon pka_strongest_basic -0.038 ChemAxon iupac 3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-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 590.7098 ChemAxon mono_mass 590.310435096 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(C=C)=C3C)N2)N1 ChemAxon formula C33H42N4O6 ChemAxon inchi InChI=1S/C33H42N4O6/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/h8,26-27,34-35H,2,7,9-15H2,1,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41) ChemAxon inchikey KSQFFJKKJAEKTB-UHFFFAOYSA-N ChemAxon polar_surface_area 164.38 ChemAxon refractivity 166.09 ChemAxon polarizability 65.82 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Specdb::CMs 17684 Specdb::CMs 38724 Specdb::NmrOneD 258648 Specdb::NmrOneD 258649 Specdb::NmrOneD 258650 Specdb::NmrOneD 258651 Specdb::NmrOneD 258652 Specdb::NmrOneD 258653 Specdb::NmrOneD 258654 Specdb::NmrOneD 258655 Specdb::NmrOneD 258656 Specdb::NmrOneD 258657 Specdb::NmrOneD 258658 Specdb::NmrOneD 258659 Specdb::NmrOneD 258660 Specdb::NmrOneD 258661 Specdb::NmrOneD 258662 Specdb::NmrOneD 258663 Specdb::NmrOneD 258664 Specdb::NmrOneD 258665 Specdb::NmrOneD 258666 Specdb::NmrOneD 258667 Specdb::MsMs 28445 Specdb::MsMs 28446 Specdb::MsMs 28447 Specdb::MsMs 35003 Specdb::MsMs 35004 Specdb::MsMs 35005 Specdb::MsMs 452026 Specdb::MsMs 2664469 Specdb::MsMs 2664470 Specdb::MsMs 2664471 Specdb::MsMs 3017805 Specdb::MsMs 3017806 Specdb::MsMs 3017807 HMDB04158 440784 389649 C05791 Urobilinogen Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Binder L, Smith D, Kupka T, Nelson B, Glass B, Wainscott M, Haynes J: Failure of prediction of liver function test abnormalities with the urine urobilinogen and urine bilirubin assays. Arch Pathol Lab Med. 1989 Jan;113(1):73-6. 2642693 Watson, C. J.; Lowry, P. T. A further study of crystalline d-urobilin. Journal of Biological Chemistry (1956), 218 633-9. Beta-glucuronidase P05804 BGLR_ECOLI uidA http://ecmdb.ca/proteins/P05804.xml Bilirubin diglucuronide + 2 Water + 3 Reduced acceptor <> D-Urobilinogen +2 D-Glucuronic acid +3 Acceptor R04979