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MedKoo Cat#: 145007 | Name: Bilirubin glucuronide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bilirubin glucuronide is a water-soluble compound that's produced in the liver and plays a key role in removing bilirubin from the body. The enzyme UGT1A1 conjugates bilirubin with glucuronic acid in the liver to form bilirubin glucuronide. Bilirubin glucuronide is the main form of bilirubin that's excreted in bile. In the bile, it's transported by MRP2, and in the blood, it's transported by MRP3. Elevated levels of bilirubin glucuronide in the blood can indicate liver problems, hepatitis, gallstones, blood infections, or sickle cell anemia. Elevated serum bilirubin glucuronides can be a biomarker of hepatotoxicity or an early indication of drug-drug interactions. Bilirubin is a toxic waste product created when heme degrades. The human body produces about 250–400 mg of bilirubin each day.

Chemical Structure

Bilirubin glucuronide
Bilirubin glucuronide
CAS#70794-57-9

Theoretical Analysis

MedKoo Cat#: 145007

Name: Bilirubin glucuronide

CAS#: 70794-57-9

Chemical Formula: C39H44N4O12

Exact Mass: 760.2956

Molecular Weight: 760.80

Elemental Analysis: C, 61.57; H, 5.83; N, 7.36; O, 25.24

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Bilirubin glucuronide;
IUPAC/Chemical Name
(2S,3S,4S,5R,6S)-6-((3-(2-((3-(2-carboxyethyl)-4-methyl-5-((Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
InChi Key
MQRFWGRFUKAJAX-LCNKTQGVSA-N
InChi Code
InChI=1S/C39H44N4O12/c1-7-20-19(6)36(50)43-27(20)14-25-17(4)22(9-11-30(44)45)28(41-25)15-29-23(18(5)24(40-29)13-26-16(3)21(8-2)37(51)42-26)10-12-31(46)54-39-34(49)32(47)33(48)35(55-39)38(52)53/h7-8,13-14,32-35,39-41,47-49H,1-2,9-12,15H2,3-6H3,(H,42,51)(H,43,50)(H,44,45)(H,52,53)/b26-13-,27-14-/t32-,33-,34+,35-,39+/m0/s1
SMILES Code
CC(C(CCC(O)=O)=C(N1)CC(N2)=C(CCC(O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(O)=O)O)O)O)=O)C(C)=C2/C=C4NC(C(C=C)=C\4C)=O)=C1/C=C(C(C=C)=C5C)\NC5=O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 760.80 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Tripathi N, Jialal I. Conjugated Hyperbilirubinemia. 2023 Jul 24. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2024 Jan–. PMID: 32965843. 2: Burchell B, Blanckaert N. Bilirubin mono- and di-glucuronide formation by purified rat liver microsomal bilirubin UDP-glucuronyltransferase. Biochem J. 1984 Oct 15;223(2):461-5. doi: 10.1042/bj2230461. PMID: 6497857; PMCID: PMC1144319. 3: Pelizzo P, Stebel M, Medic N, Sist P, Vanzo A, Anesi A, Vrhovsek U, Tramer F, Passamonti S. Cyanidin 3-glucoside targets a hepatic bilirubin transporter in rats. Biomed Pharmacother. 2023 Jan;157:114044. doi: 10.1016/j.biopha.2022.114044. Epub 2022 Dec 1. PMID: 36463829. 4: Sieg A, Vaclavsky J, Stiehl A, Raedsch R, Czygan P, Kommerell B. Isomers of bilirubin glucuronide in serum and bile before and after relief of common duct obstruction. J Hepatol. 1986;3(3):341-7. doi: 10.1016/s0168-8278(86)80487-1. PMID: 3559144. 5: Thompson RP, Hofmann AF. Chemical synthesis of bilirubin glucuronide conjugates. Biochim Biophys Acta. 1976 Nov 18;451(1):267-77. doi: 10.1016/0304-4165(76)90277-4. PMID: 1009109. 6: Hauser SC, Ziurys JC, Gollan JL. Regulation of bilirubin glucuronide synthesis in primate (Macaca fascicularis) liver. Kinetic analysis of microsomal bilirubin uridine diphosphate glucuronyltransferase. Gastroenterology. 1986 Aug;91(2):287-96. doi: 10.1016/0016-5085(86)90559-7. PMID: 3087808. 7: Kamisako T, Kobayashi Y, Takeuchi K, Ishihara T, Higuchi K, Tanaka Y, Gabazza EC, Adachi Y. Recent advances in bilirubin metabolism research: the molecular mechanism of hepatocyte bilirubin transport and its clinical relevance. J Gastroenterol. 2000;35(9):659-64. doi: 10.1007/s005350070044. PMID: 11023036. 8: Tanaka Y, Kobayashi Y, Gabazza EC, Higuchi K, Kamisako T, Kuroda M, Takeuchi K, Iwasa M, Kaito M, Adachi Y. Increased renal expression of bilirubin glucuronide transporters in a rat model of obstructive jaundice. Am J Physiol Gastrointest Liver Physiol. 2002 Apr;282(4):G656-62. doi: 10.1152/ajpgi.00383.2001. PMID: 11897625. 9: SCHMID R. Direct-reacting bilirubin, bilirubin glucuronide, in serum, bile and urine. Science. 1956 Jul 13;124(3211):76-7. doi: 10.1126/science.124.3211.76. PMID: 13337353. 10: ARIAS IM, LONDON IM. Bilirubin glucuronide formation in vitro; demonstration of a defect in Gilbert's disease. Science. 1957 Sep 20;126(3273):563-4. doi: 10.1126/science.126.3273.563. PMID: 13467249. 11: SCHMID R. The identification of direct-reacting bilirubin as bilirubin glucuronide. J Biol Chem. 1957 Dec;229(2):881-8. PMID: 13502349. 12: Van Roy FP, Heirwegh KP. Determination of bilirubin glucuronide and assay of glucuronyltransferase with bilirubin as acceptor. Biochem J. 1968 Apr;107(4):507-18. doi: 10.1042/bj1070507. PMID: 5660631; PMCID: PMC1198694. 13: Okolicsanyi L, Magnenat P, Frei J. Deconjugation of bilirubin glucuronide by the liver. Lancet. 1968 Jun 1;1(7553):1173-4. doi: 10.1016/s0140-6736(68)91867-9. PMID: 4172291. 14: Sodani K, Patel A, Kathawala RJ, Chen ZS. Multidrug resistance associated proteins in multidrug resistance. Chin J Cancer. 2012 Feb;31(2):58-72. doi: 10.5732/cjc.011.10329. Epub 2011 Nov 18. PMID: 22098952; PMCID: PMC3777468. 15: SCHMID R, HAMMAKER L, AXELROD J. The enzymatic formation of bilirubin glucuronide. Arch Biochem Biophys. 1957 Jul;70(1):285-8. doi: 10.1016/0003-9861(57)90103-0. PMID: 13445265. 16: Iyanagi T, Emi Y, Ikushiro S. Biochemical and molecular aspects of genetic disorders of bilirubin metabolism. Biochim Biophys Acta. 1998 Sep 30;1407(3):173-84. doi: 10.1016/s0925-4439(98)00044-1. PMID: 9748558. 17: Saxerholt H, Skar V, Midtvedt T. HPLC separation and quantification of bilirubin and its glucuronide conjugates in faeces and intestinal contents of germ-free rats. Scand J Clin Lab Invest. 1990 Sep;50(5):487-95. doi: 10.1080/00365519009089163. PMID: 2237261. 18: Omori H, Chikamoto J, Nagahara M, Hirata M, Otoi T. Evaluating variations in bilirubin glucuronidation activity by protease inhibitors in canine and human primary hepatocytes cultured in a 3D culture system. Toxicol In Vitro. 2023 Dec;93:105689. doi: 10.1016/j.tiv.2023.105689. Epub 2023 Sep 1. PMID: 37660998. 19: Chowdhury JR, Chowdhury NR, Gärtner U, Wolkoff AW, Arias IM. Bilirubin diglucuronide formation in intact rats and in isolated Gunn rat liver. J Clin Invest. 1982 Mar;69(3):595-603. doi: 10.1172/jci110486. PMID: 6801091; PMCID: PMC371016. 20: Mazza T, Roumeliotis TI, Garitta E, Drew D, Rashid ST, Indiveri C, Choudhary JS, Linton KJ, Beis K. Structural basis for the modulation of MRP2 activity by phosphorylation and drugs. Nat Commun. 2024 Mar 4;15(1):1983. doi: 10.1038/s41467-024-46392-8. PMID: 38438394; PMCID: PMC10912322.

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BIM-46050

BIM-46050