CHEBI:28860 - β-D-glucuronic acid

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ChEBI Name β-D-glucuronic acid
ChEBI ID CHEBI:28860
ChEBI ASCII Name beta-D-glucuronic acid
Definition A D-glucopyranuronic acid in which the anomeric centre has β-configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40973, CHEBI:10395, CHEBI:21016
Supplier Information eMolecules:30069645, ZINC000004097543
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Wikipedia License
Glucuronic acid (from Greek γλεῦκος "sweet wine, must" and οὖρον "urine") is a uronic acid that was first isolated from urine (hence the name "uronic acid"). It is found in many gums such as gum arabic (approx. 18%), xanthan, and kombucha tea and is important for the metabolism of microorganisms, plants and animals.
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Formula C6H10O7
Net Charge 0
Average Mass 194.13940
Monoisotopic Mass 194.04265
InChI InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6+/m0/s1
InChIKey AEMOLEFTQBMNLQ-QIUUJYRFSA-N
SMILES O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
Metabolite of Species Details
Daphnia magna (NCBI:txid35525) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
(via D-glucopyranuronic acid )
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via glucuronic acid )
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
(via glucuronic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing β-D-glucuronic acid (CHEBI:28860) has role metabolite (CHEBI:25212)
β-D-glucuronic acid (CHEBI:28860) is a D-glucopyranuronic acid (CHEBI:47952)
β-D-glucuronic acid (CHEBI:28860) is conjugate acid of β-D-glucuronate (CHEBI:85313)
Incoming α-D-GlcpNAc-(1→4)-β-D-GlcpA (CHEBI:150151) has functional parent β-D-glucuronic acid (CHEBI:28860)
β-D-GlcpA-(1→3)-β-D-GalpNAc4S (CHEBI:145591) has functional parent β-D-glucuronic acid (CHEBI:28860)
β-D-GlcpA-(1→3)-β-D-GalpNAc6S (CHEBI:145588) has functional parent β-D-glucuronic acid (CHEBI:28860)
β-D-GlcpA-(1→4)-D-Xylp (CHEBI:150112) has functional parent β-D-glucuronic acid (CHEBI:28860)
β-D-GlcpNAc-(1→4)-β-D-GlcpA (CHEBI:150712) has functional parent β-D-glucuronic acid (CHEBI:28860)
β-D-glucuronamide (CHEBI:32323) has functional parent β-D-glucuronic acid (CHEBI:28860)
β-D-Xylp-(1→3)-β-D-GlcpA (CHEBI:149024) has functional parent β-D-glucuronic acid (CHEBI:28860)
β-D-Xylp-(1→4)-β-D-GlcpA (CHEBI:151572) has functional parent β-D-glucuronic acid (CHEBI:28860)
2-Me-α-D-Fucp4NAc-(1→4)-β-D-GlcpA (CHEBI:59383) has functional parent β-D-glucuronic acid (CHEBI:28860)
3-indole carboxylic acid glucuronide (CHEBI:68486) has functional parent β-D-glucuronic acid (CHEBI:28860)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide) (CHEBI:88730) has functional parent β-D-glucuronic acid (CHEBI:28860)
5-(3',5'-dihydroxyphenyl)-valeric acid-O-glucuronide (CHEBI:149595) has functional parent β-D-glucuronic acid (CHEBI:28860)
acetaminophen O-β-D-glucosiduronic acid (CHEBI:32636) has functional parent β-D-glucuronic acid (CHEBI:28860)
androsterone 3-glucosiduronic acid (CHEBI:28832) has functional parent β-D-glucuronic acid (CHEBI:28860)
atractyligenin 2-glucuronide (CHEBI:196976) has functional parent β-D-glucuronic acid (CHEBI:28860)
cytosylglucuronic acid (CHEBI:132133) has functional parent β-D-glucuronic acid (CHEBI:28860)
dehydroisoandrosterone 3-glucuronide (CHEBI:68834) has functional parent β-D-glucuronic acid (CHEBI:28860)
kaempferol O-glucuronide (CHEBI:75720) has functional parent β-D-glucuronic acid (CHEBI:28860)
luteolin O-glucuronoside (CHEBI:25091) has functional parent β-D-glucuronic acid (CHEBI:28860)
methyl β-D-glucopyranuronate (CHEBI:145605) has functional parent β-D-glucuronic acid (CHEBI:28860)
methyl β-D-glucuronoside (CHEBI:53688) has functional parent β-D-glucuronic acid (CHEBI:28860)
mycophenolic acid O-acyl-glucuronide (CHEBI:64689) has functional parent β-D-glucuronic acid (CHEBI:28860)
myricetin O-glucuronide (CHEBI:75806) has functional parent β-D-glucuronic acid (CHEBI:28860)
octanoyl-β-D-glucuronide (CHEBI:71003) has functional parent β-D-glucuronic acid (CHEBI:28860)
β-D-glucuronate (CHEBI:85313) is conjugate base of β-D-glucuronic acid (CHEBI:28860)
IUPAC Names
(2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylic acid
β-D-glucopyranuronic acid
Synonyms Sources
β-D-GlcpA IUPAC
beta-D-Glucopyranuronic acid KEGG COMPOUND
β-D-glucopyranuronic acid ChEBI
beta-D-Glucuronic acid KEGG COMPOUND
GlcAb ChEBI
GlcAβ ChEBI
Manual Xrefs Databases
BDP PDBeChem
C00001123 KNApSAcK
C08350 KEGG COMPOUND
CPD-12521 MetaCyc
Glucuronic_acid Wikipedia
View more database links
Registry Numbers Types Sources
1427744 Reaxys Registry Number Reaxys
2497864 Gmelin Registry Number Gmelin
Citations
Kaur D, Moreira D, Coimbra S, Showalter AM (2022)
Hydroxyproline-O-Galactosyltransferases Synthesizing Type II Arabinogalactans Are Essential for Male Gametophytic Development in Arabidopsis.
Frontiers in plant science 13, 935413 [PubMed:35774810]
[show Abstract]
Jandus P, Boligan KF, Smith DF, de Graauw E, Grimbacher B, Jandus C, Abdelhafez MM, Despont A, Bovin N, Simon D, Rieben R, Simon HU, Cummings RD, von Gunten S (2019)
The architecture of the IgG anti-carbohydrate repertoire in primary antibody deficiencies.
Blood 134, 1941-1950 [PubMed:31537530]
[show Abstract]
Schneider C, Smith DF, Cummings RD, Boligan KF, Hamilton RG, Bochner BS, Miescher S, Simon HU, Pashov A, Vassilev T, von Gunten S (2015)
The human IgG anti-carbohydrate repertoire exhibits a universal architecture and contains specificity for microbial attachment sites.
Science translational medicine 7, 269ra1 [PubMed:25568069]
[show Abstract]
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]
von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS (2009)
Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass.
The Journal of allergy and clinical immunology 123, 1268-76.e15 [PubMed:19443021]
[show Abstract]
Last Modified
06 September 2023