UDP-alpha-D-glucuronic acid (CHEBI:17200)

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CHEBI:17200 - UDP-α-D-glucuronic acid

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ChEBI Name	UDP-α-D-glucuronic acid

ChEBI ID	CHEBI:17200

ChEBI ASCII Name	UDP-alpha-D-glucuronic acid

Definition	A UDP-sugar having α-D-glucuronic acid as the sugar component.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:46309, CHEBI:13506, CHEBI:13489, CHEBI:9846, CHEBI:22104

Supplier Information	ZINC000008215691

Download	Molfile XML SDF

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3 4 1 0 0 0 0

4 27 1 0 0 0 0

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6 4 1 0 0 0 0

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7 8 1 0 0 0 0

7 11 1 0 0 0 0

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37 59 1 0 0 0 0

M END): 18 ms

reading 59 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

59 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Wikipedia	License
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.
Read full article at Wikipedia

Formula

C15H22N2O18P2

Net Charge

Average Mass

580.28538

Monoisotopic Mass

580.03429

InChI

InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1

InChIKey

HDYANYHVCAPMJV-LXQIFKJMSA-N

SMILES

O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	See: MetaboLights Study

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	UDP-α-D-glucuronic acid (CHEBI:17200) has functional parent α-D-glucuronic acid (CHEBI:42717) UDP-α-D-glucuronic acid (CHEBI:17200) has role Escherichia coli metabolite (CHEBI:76971) UDP-α-D-glucuronic acid (CHEBI:17200) has role human metabolite (CHEBI:77746) UDP-α-D-glucuronic acid (CHEBI:17200) has role mouse metabolite (CHEBI:75771) UDP-α-D-glucuronic acid (CHEBI:17200) is a UDP-D-glucuronic acid (CHEBI:197331) UDP-α-D-glucuronic acid (CHEBI:17200) is conjugate acid of UDP-α-D-glucuronate(3−) (CHEBI:58052)

Incoming	UDP-2,3-diacetamido-2,3-dideoxy-α-D-glucuronic acid (CHEBI:48402) has functional parent UDP-α-D-glucuronic acid (CHEBI:17200) UDP-α-D-glucuronate(3−) (CHEBI:58052) is conjugate base of UDP-α-D-glucuronic acid (CHEBI:17200)

IUPAC Name

uridine 5'-[3-(α-D-glucopyranuronosyl) dihydrogen diphosphate]

Synonyms	Sources
UDP-alpha-D-glucuronate	KEGG COMPOUND
UDP-D-glucuronate	KEGG COMPOUND
UDPglucuronate	KEGG COMPOUND
UDPglucuronate	KEGG COMPOUND
uridine diphosphate glucuronic acid	ChemIDplus
URIDINE-5'-DIPHOSPHATE-GLUCURONIC ACID	PDBeChem

Manual Xrefs	Databases
C00007238	KNApSAcK
C00167	KEGG COMPOUND
G10612	KEGG GLYCAN
HMDB0000935	HMDB
UGA	PDBeChem
Uridine_diphosphate_glucuronic_acid	Wikipedia
View more database links

Registry Numbers	Types	Sources
2616-64-0	CAS Registry Number	ChemIDplus
78881	Reaxys Registry Number	Reaxys

Citations

Guyett P, Glushka J, Gu X, Bar-Peled M (2009)
Real-time NMR monitoring of intermediates and labile products of the bifunctional enzyme UDP-apiose/UDP-xylose synthase.
Carbohydrate research 344, 1072-1078 [PubMed:19375693]
[show Abstract]

Gu X, Wages CJ, Davis KE, Guyett PJ, Bar-Peled M (2009)
Enzymatic characterization and comparison of various poaceae UDP-GlcA 4-epimerase isoforms.
Journal of biochemistry 146, 527-534 [PubMed:19564155]
[show Abstract]

Lattard V, Fondeur-Gelinotte M, Gulberti S, Jacquinet JC, Boudrant J, Netter P, Magdalou J, Ouzzine M, Fournel-Gigleux S (2006)
Purification and characterization of a soluble form of the recombinant human galactose-beta1,3-glucuronosyltransferase I expressed in the yeast Pichia pastoris.
Protein expression and purification 47, 137-143 [PubMed:16300963]
[show Abstract]

Cappiello M, Giuliani L, Rane A, Pacifici GM (2000)
Uridine 5'-diphosphoglucuronic acid (UDPGLcUA) in the human fetal liver, kidney and placenta.
European journal of drug metabolism and pharmacokinetics 25, 161-163 [PubMed:11420884]
[show Abstract]

TAKETA K (1962)
Enzymatic studies of glucuronide formation in impaired liver. IV. Liver glucuronyl transferase activity and uridine diphosphate glucuronic acid content in viral hepatitis patients.
Acta medicinae Okayama 16, 115-128 [PubMed:13984680]

STOREY ID, DUTTON GJ (1955)
Uridine compounds in glucuronic acid metabolism. 2. The isolation and structure of 'uridine-diphosphate-glucuronic acid'.
The Biochemical journal 59, 279-288 [PubMed:14351193]

Last Modified

25 September 2023

CHEBI:17200 - UDP-α-D-glucuronic acid

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