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Uridine diphosphate glucuronic acid information


Uridine diphosphate glucuronic acid
Names
IUPAC name
3-[(5′-Deoxyuridin-5′-yl)oxy]-1,3-dihydroxy-1,3-dioxo-1λ5,3λ5-diphosphoxan-1-yl α-D-glucopyranosiduronic acid
Systematic IUPAC name
(2S,3S,4S,5R,6R)-6-[(3-{[(2R,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}-1,3-dihydroxy-1,3-dioxo-1λ5,3λ5-diphosphoxan-1-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Identifiers
CAS Number
  • 2616-64-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17200 ☒N
ChemSpider
  • 19951236 checkY
IUPHAR/BPS
  • 1784
MeSH UDP+glucuronic+acid
PubChem CID
  • 17473
UNII
  • 04SZC4MEFQ checkY
CompTox Dashboard (EPA)
  • DTXSID00903961 Edit this at Wikidata
InChI
  • InChI=1S/C9H12N2O6.C6H12O13P2/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16;7-1-2(18-20(12,13)14)5(19-21(15,16)17)3(8)4(9)6(10)11/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16);1-5,8-9H,(H,10,11)(H2,12,13,14)(H2,15,16,17)/p-4/t4-,6-,7-,8-;2-,3+,4-,5+/m10/s1 checkY
    Key: GIFKDHYZEJQSDD-BZYIUNRFSA-J checkY
  • InChI=1/C9H12N2O6.C6H12O13P2/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16;7-1-2(18-20(12,13)14)5(19-21(15,16)17)3(8)4(9)6(10)11/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16);1-5,8-9H,(H,10,11)(H2,12,13,14)(H2,15,16,17)/p-4/t4-,6-,7-,8-;2-,3+,4-,5+/m10/s1
    Key: GIFKDHYZEJQSDD-DNQFPBLIBB
SMILES
  • O[C@@H]1[C@@H](O)[C@H](O[C@@H]([C@H]1O)C(O)=O)O[P](O)(=O)O[P](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)[N]3C=C[C](=O)[NH][C]3=O
Properties
Chemical formula
C15H22N2O18P2
Molar mass 580.285
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

UDP-glucuronic acid is a sugar used in the creation of polysaccharides and is an intermediate in the biosynthesis of ascorbic acid (except in primates and guinea pigs). It also participates in the heme degradation process of human.

It is made from UDP-glucose by UDP-glucose 6-dehydrogenase (EC 1.1.1.22) using NAD+ as a cofactor. It is the source of the glucuronosyl group in glucuronosyltransferase reactions.[1][2]

  1. ^ Bontemps Y, Vuillermoz B, Antonicelli F, Perreau C, Danan JL, Maquart FX, Wegrowski Y (Jun 2003). "Specific protein-1 is a universal regulator of UDP-glucose dehydrogenase expression: its positive involvement in transforming growth factor-beta signaling and inhibition in hypoxia". The Journal of Biological Chemistry. 278 (24): 21566–75. doi:10.1074/jbc.M209366200. PMID 12682078.
  2. ^ Sommer BJ, Barycki JJ, Simpson MA (May 2004). "Characterization of human UDP-glucose dehydrogenase. CYS-276 is required for the second of two successive oxidations". The Journal of Biological Chemistry. 279 (22): 23590–6. doi:10.1074/jbc.M401928200. PMID 15044486.

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Uridine diphosphate glucuronic acid

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UDP-glucuronic acid is a sugar used in the creation of polysaccharides and is an intermediate in the biosynthesis of ascorbic acid (except in primates...

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Uridine diphosphate glucose

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Uridine diphosphate glucose (uracil-diphosphate glucose, UDP-glucose) is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism...

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Glucuronidation

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of uridine diphosphate glucuronic acid to a substrate by any of several types of UDP-glucuronosyltransferase. UDP-glucuronic acid (glucuronic acid linked...

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Glucuronosyltransferase

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consists of the transfer of the glucuronosyl group from uridine 5'-diphospho-glucuronic acid (UDPGA) to substrate molecules that contain oxygen, nitrogen...

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David Sidney Feingold

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Uridine diphosphate N-acetylglucosamine and uridine diphosphate glucuronic acid in mung bean seedlings. Enzymatic synthesis of uridine diphosphate glucuronic...

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UDPG

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UDPG may refer to: Uridine diphosphate glucose Uridine diphosphate glucuronic acid This set index article lists chemical compounds articles associated...

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UGT2B7

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with glucuronic acid, using uridine diphosphate glucuronic acid. Together with UGT2B4, UGT2B7 is capable of glucosidation of hyodesoxycholic acid in the...

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Glycosidic bond

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phosphate group of a nucleotide such as uridine diphosphate (UDP), guanosine diphosphate (GDP), thymidine diphosphate (TDP), or cytidine monophosphate (CMP)...

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Bioenhancer

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hydroxylase (AHH), ethylmorphine N-demethylase, Uridine diphosphate glucuronic_acid, Uridine diphosphate glucuronyltransferase (UGT), P-glycoprotein, CYP2EI...

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Bilirubin

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the hepatocytes and subsequently conjugated with glucuronic acid (via the enzyme uridine diphosphate–glucuronyl transferase). In this state, bilirubin...

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Chlornaphazine

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in the liver is the conjugation with glucuronic acid for which the cosubstrate uridine diphosphate-glucuronic acid (UDPGA) and enzyme UDP-glucuronosyltransferase...

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Mycoestrogen

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transferase UGT (5'-diphosphate glucuronosyltransferase) adds a glucuronic acid group sourced from uridine 5'-diphosphate glucuronic acid (UDPGA). Mycoestrogens...

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UXS1

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UDP-glucuronic acid decarboxylase 1 is an enzyme that in humans is encoded by the UXS1 gene. UDP-glucuronate decarboxylase (UGD; EC 4.1.1.35) catalyzes...

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