Bilirubin diglucuronide

Bilirubin di-glucuronide is a conjugated form of bilirubin formed in bilirubin metabolism.[1] The hydrophilic character of bilirubin diglucuronide enables it to be water-soluble. It is pumped across the hepatic canalicular membrane into the bile by the transporter MRP2.[2]

Bilirubin diglucuronide
Names
IUPAC name
(2,17-Diethenyl-3,7,13,18-tetramethyl-1,19-dioxo-10,19,21,22,23,24-hexahydro-1H-biline-8,12-diyl)bis(1-oxopropane-3,1-diyl) di(β-D-glucopyranosiduronic acid)
Systematic IUPAC name
(12S,13R,14S,15S,16S,132S,133R,134S,135S,136S)-65-[(Z)-(3-Ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-85-[(Z)-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-13,14,15,133,134,135-hexahydroxy-64,84-dimethyl-3,11-dioxo-61H,81H-2,12-dioxa-6(3,2),8(2,3)-dipyrrola-1,13(2)-bis(oxana)tridecaphane-16,136-dicarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
MeSH bilirubin+diglucuronide
UNII
  • InChI=1S/C45H52N4O18/c1-7-20-19(6)40(58)49-27(20)14-25-18(5)23(10-12-31(51)65-45-37(57)33(53)35(55)39(67-45)43(62)63)29(47-25)15-28-22(17(4)24(46-28)13-26-16(3)21(8-2)41(59)48-26)9-11-30(50)64-44-36(56)32(52)34(54)38(66-44)42(60)61/h7-8,13-14,32-39,44-47,52-57H,1-2,9-12,15H2,3-6H3,(H,48,59)(H,49,58)(H,60,61)(H,62,63)/b26-13+,27-14+/t32-,33-,34-,35-,36+,37+,38-,39-,44+,45+/m0/s1 ☒N
    Key: SCJLWMXOOYZBTH-SDXZDYKGSA-N ☒N
  • InChI=1/C45H52N4O18/c1-7-20-19(6)40(58)49-27(20)14-25-18(5)23(10-12-31(51)65-45-37(57)33(53)35(55)39(67-45)43(62)63)29(47-25)15-28-22(17(4)24(46-28)13-26-16(3)21(8-2)41(59)48-26)9-11-30(50)64-44-36(56)32(52)34(54)38(66-44)42(60)61/h7-8,13-14,32-39,44-47,52-57H,1-2,9-12,15H2,3-6H3,(H,48,59)(H,49,58)(H,60,61)(H,62,63)/b26-13+,27-14+/t32-,33-,34-,35-,36+,37+,38-,39-,44+,45+/m0/s1
    Key: SCJLWMXOOYZBTH-SDXZDYKGBT
  • Cc1c(c([nH]c1/C=C/2\C(=C(C(=O)N2)C=C)C)Cc3c(c(c([nH]3)/C=C/4\C(=C(C(=O)N4)C)C=C)C)CCC(=O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)CCC(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O
Properties
C45H52N4O18
Molar mass 936.911 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

References
  1. Chowdhury, J. R.; Chowdhury, N. R.; Wu, G.; Shouval, R.; Arias, I. M. (1981). "Bilirubin mono- and diglucuronide formation by human liver in vitro: Assay by high-pressure liquid chromatography". Hepatology. 1 (6): 622–7. doi:10.1002/hep.1840010610. PMID 6796486.
  2. Lengyel, G.; et al. (2007-08-29). "Modulation of sinusoidal and canalicular elimination of bilirubin-glucuronides by rifampicin and other cholestatic drugs in a sandwich culture of rat hepatocytes". Hepatology Research. Wiley. 38 (3): 300–309. doi:10.1111/j.1872-034X.2007.00255.x. PMID 17760873.


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