17459-92-6
Chemical Structure
Bilirubin diglucuronide
- CAS No.: 17459-92-6
- Formula:C45H52N4O18
- Molecular Weight:936.91
IUPAC Name: (2S,3S,4S,5R,6S)-6-((3-(2-((3-(3-(((2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-oxopropyl)-4-methyl-5-((Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
InChIKey: SCJLWMXOOYZBTH-BTVQFETGSA-N
SMILES: OC([C@H]([C@H]([C@@H]([C@H]1O)O)O)O[C@H]1OC(CCC(C(C)=C(N2)/C=C3C(C=C)=C(C(N/3)=O)C)=C2CC4=C(C(C)=C(N4)/C=C5C(C)=C(C(N/5)=O)C=C)CCC(O[C@@H]6O[C@@H]([C@H]([C@@H]([C@H]6O)O)O)C(O)=O)=O)=O)=O
Biological Activity: Bilirubin diglucuronide is a bilirubin glycoside conjugate with a 1-O-acyl β-D-glucuronide structure. Bilirubin diglucuronide is the major conjugated bilirubin (HY-N0323) and predominant pigment excreted in the bile of adult humans, rats, dogs and cats. Bilirubin diglucuronide is mainly synthesized via UDP-glucuronosyltransferase-mediated transfer of glucuronic acid from UDP-glucuronic acid to bilirubin monoglucuronide, or via enzymatic disproportionation of two moles of bilirubin monoglucuronide (predominantly producing the IXα configuration). In addition, Bilirubin diglucuronide can also be synthesized from bilirubin or its monoglucuronide in a UDP-glucuronic acid-dependent manner. Pretreatment with phenobarbital significantly enhances the formation process of Bilirubin diglucuronide[1][2].
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Bilirubin diglucuronide | Bilirubin diglucuronide is a bilirubin glycoside conjugate with a 1-O-acyl β-D-glucuronide structure. Bilirubin diglucuronide is the major conjugated bilirubin (HY-N0323) and predominant pigment excreted in the bile of adult humans, rats, dogs and cats. Bilirubin diglucuronide is mainly synthesized via UDP-glucuronosyltransferase-mediated transfer of glucuronic acid from UDP-glucuronic acid to bilirubin monoglucuronide, or via enzymatic disproportionation of two moles of bilirubin monoglucuronide (predominantly producing the IXα configuration). In addition, Bilirubin diglucuronide can also be synthesized from bilirubin or its monoglucuronide in a UDP-glucuronic acid-dependent manner. Pretreatment with phenobarbital significantly enhances the formation process of Bilirubin diglucuronide. | |||||||||||||||||||||
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- [1]. Chowdhury JR, et al. Bilirubin mono- and diglucuronide formation by human liver in vitro: assay by high-pressure liquid chromatography. Hepatology. 1981;1(6):622-627. [Content Brief]
- [2]. Blanckaert N, et al. Bilirubin diglucuronide synthesis by a UDP-glucuronic acid-dependent enzyme system in rat liver microsomes. Proc Natl Acad Sci U S A. 1979;76(4):2037-2041. [Content Brief]
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