Bilirubin diglucuronide

Bilirubin diglucuronide
Identifiers

CAS Registry Number	17459-92-6^Y
ChemSpider	4573640^N
InChI 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
Jmol-3D images	Image
MeSH	bilirubin+diglucuronide
PubChem	5280817
SMILES 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
Chemical formula	C₄₅H₅₂N₄O₁₈
Molar mass	936.911 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Bilirubin diglucuronide is a conjugated form of bilirubin formed in bilirubin metabolism. 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.^[1]

References

↑ 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.

Heme metabolic intermediates

Porphyrin biosynthesis

early mitochondrial:	D-Aminolevulinic acid

cytosolic:	Porphobilinogen Hydroxymethylbilane Uroporphyrinogen III Coproporphyrinogen III

late mitochondrial:	Protoporphyrinogen IX Protoporphyrin IX

Heme degradation
and excretion

Breakdown of heme

spleen:	Heme → Biliverdin → Bilirubin

blood:	Bilirubin+Albumin

liver:	Bilirubin diglucuronide

Intestine, excretion in feces

Kidney, excretion in urine

Urobilin

Index of cells from bone marrow

Description	Immune system Cells Physiology coagulation proteins granule contents colony-stimulating heme and porphyrin metabolism intermediates

Disease	Red blood cell Monocyte and granulocyte Neoplasms and cancer Histiocytosis Symptoms and signs eponymous Blood tests findings

Treatment	Transfusion Drugs thrombosis bleeding other

Bilirubin diglucuronide

See also

References