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Uridine diphosphate glucuronic acid: Difference between revisions

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Revision as of 10:12, 17 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit Latest revision as of 17:24, 5 September 2023 edit undoTom282f3 (talk | contribs)310 editsm Heme degradationTag: 2017 wikitext editor 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ |ImageFile=UDP glucuronic acid.png
| verifiedrevid = 470620417
⚫ |ImageSize=200px
⚫ | ImageFile=Uridine diphosphate glucuronic acid.svg
|IUPACName=
⚫ | ImageSize=200px
⚫ |OtherNames=
| IUPACName=3--1,3-dihydroxy-1,3-dioxo-1λ<sup>5</sup>,3λ<sup>5</sup>-diphosphoxan-1-yl α-<small>D</small>-glucopyranosiduronic acid
⚫ |Section1= {{Chembox Identifiers
| SystematicName=(2''S'',3''S'',4''S'',5''R'',6''R'')-6-methoxy}-1,3-dihydroxy-1,3-dioxo-1λ<sup>5</sup>,3λ<sup>5</sup>-diphosphoxan-1-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
⚫ | 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
⚫ | OtherNames=
⚫ |Section1={{Chembox Identifiers
⚫ | 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
| InChIKey = GIFKDHYZEJQSDD-DNQFPBLIBB | InChIKey = GIFKDHYZEJQSDD-DNQFPBLIBB
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GIFKDHYZEJQSDD-BZYIUNRFSA-J | StdInChIKey = GIFKDHYZEJQSDD-BZYIUNRFSA-J
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=2616-64-0 | CASNo=2616-64-0
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem=17473
| UNII = 04SZC4MEFQ
⚫ | ChemSpiderID=19951236
⚫ | PubChem=17473
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID=19951236
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 17200
| IUPHAR_ligand = 1784 | IUPHAR_ligand = 1784
| SMILES = OC(=O)(O)(O)(OP()()=O)(C=O)OP()()=O.O=C\1NC(=O)N(/C=C/1)2O(CO)(O)2O | SMILES = O1(O)(O(1O)C(O)=O)O(O)(=O)O(O)(=O)OC2O((O)2O)3C=C(=O)3=O
| MeSHName=UDP+glucuronic+acid | MeSHName=UDP+glucuronic+acid
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>15</sub>H<sub>22</sub>N<sub>2</sub>O<sub>18</sub>P<sub>2</sub> | Formula=C<sub>15</sub>H<sub>22</sub>N<sub>2</sub>O<sub>18</sub>P<sub>2</sub>
| MolarMass=580.285 | MolarMass=580.285
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
'''UDP glucuronic acid''' is a ] used in the creation of ]s and is an intermediate in the biosynthesis of ] (except in ]s and ]s). '''UDP-glucuronic acid''' is a ] used in the creation of ]s and is an intermediate in the biosynthesis of ] (except in ]s and ]s). It also participates in the ] of human.


It is made from ] by ] (EC 1.1.1.22) using ] as a cofactor. It is the source of the glucuronosyl group in ] reactions.<ref>{{cite journal | vauthors = Bontemps Y, Vuillermoz B, Antonicelli F, Perreau C, Danan JL, Maquart FX, Wegrowski Y | title = 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 | journal = The Journal of Biological Chemistry | volume = 278 | issue = 24 | pages = 21566–75 | date = Jun 2003 | pmid = 12682078 | doi = 10.1074/jbc.M209366200 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Sommer BJ, Barycki JJ, Simpson MA | title = Characterization of human UDP-glucose dehydrogenase. CYS-276 is required for the second of two successive oxidations | journal = The Journal of Biological Chemistry | volume = 279 | issue = 22 | pages = 23590–6 | date = May 2004 | pmid = 15044486 | doi = 10.1074/jbc.M401928200 | doi-access = free }}</ref>
It is made from ] by ] (EC 1.1.1.22) using ] as a cofactor. It is the source of the glucuronosyl group in ] reactions.


==See also== ==See also==
* ] * ]
* ] * ]

== References ==
{{reflist}}


{{Nucleotide sugars}} {{Nucleotide sugars}}


] ]
]
] ]
] ]
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{{biochem-stub}} {{biochem-stub}}

]
]

Latest revision as of 17:24, 5 September 2023

Uridine diphosphate glucuronic acid
Names
IUPAC name 3--1,3-dihydroxy-1,3-dioxo-1λ,3λ-diphosphoxan-1-yl α-D-glucopyranosiduronic acid
Systematic IUPAC name (2S,3S,4S,5R,6R)-6-methoxy}-1,3-dihydroxy-1,3-dioxo-1λ,3λ-diphosphoxan-1-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
IUPHAR/BPS
MeSH UDP+glucuronic+acid
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: GIFKDHYZEJQSDD-BZYIUNRFSA-J
  • 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/s1Key: GIFKDHYZEJQSDD-DNQFPBLIBB
SMILES
  • O1(O)(O(1O)C(O)=O)O(O)(=O)O(O)(=O)OC2O((O)2O)3C=C(=O)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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

See also

References

  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.
Types of nucleotide sugars


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