2.02012-05-31 14:53:57 -06002015-06-03 17:20:24 -0600ECMDB21000M2MDB001421D-UrobilinogenUrobilinogen 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-UrobilinogenUrobilinogenC33H42N4O6590.7098590.3104350963-(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 acid3-(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 acid17208-65-0CCC1=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)N1InChI=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-NSolidInner membraneMembraneOuter membranelogp2.77logs-4.46solubility2.05e-02 g/llogp3.46pka_strongest_acidic4.06pka_strongest_basic-0.038iupac3-(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 acidaverage_mass590.7098mono_mass590.310435096smilesCCC1=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)N1formulaC33H42N4O6inchiInChI=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)inchikeyKSQFFJKKJAEKTB-UHFFFAOYSA-Npolar_surface_area164.38refractivity166.09polarizability65.82rotatable_bond_count14acceptor_count6donor_count6physiological_charge-2formal_charge0Porphyrin and chlorophyll metabolismec00860Specdb::CMs17684Specdb::CMs38724Specdb::NmrOneD258648Specdb::NmrOneD258649Specdb::NmrOneD258650Specdb::NmrOneD258651Specdb::NmrOneD258652Specdb::NmrOneD258653Specdb::NmrOneD258654Specdb::NmrOneD258655Specdb::NmrOneD258656Specdb::NmrOneD258657Specdb::NmrOneD258658Specdb::NmrOneD258659Specdb::NmrOneD258660Specdb::NmrOneD258661Specdb::NmrOneD258662Specdb::NmrOneD258663Specdb::NmrOneD258664Specdb::NmrOneD258665Specdb::NmrOneD258666Specdb::NmrOneD258667Specdb::MsMs28445Specdb::MsMs28446Specdb::MsMs28447Specdb::MsMs35003Specdb::MsMs35004Specdb::MsMs35005Specdb::MsMs452026Specdb::MsMs2664469Specdb::MsMs2664470Specdb::MsMs2664471Specdb::MsMs3017805Specdb::MsMs3017806Specdb::MsMs3017807HMDB04158440784389649C05791UrobilinogenKanehisa, 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-D114.22080510Binder 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):73-6.2642693Watson, C. J.; Lowry, P. T. A further study of crystalline d-urobilin. Journal of Biological Chemistry (1956), 218 633-9. Beta-glucuronidaseP05804BGLR_ECOLIuidAhttp://ecmdb.ca/proteins/P05804.xmlBilirubin diglucuronide + 2 Water + 3 Reduced acceptor <> D-Urobilinogen +2 D-Glucuronic acid +3 AcceptorR04979