Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Compound: β-D-glucuronate

Synonyms: β-D-glucuronic acid, β-D-glucopyranuronic acid

Superclasses: all carbohydrates a carbohydrate a glycan a sugar a monosaccharide a hexose a D-hexose D-glucuronate D-glucopyranuronate
an acid all carboxy acids a carboxylate D-glucuronate D-glucopyranuronate

Summary:
D-glucuronate is a carboxylic acid that often forms a hexapyranose ring structure. The hexapyranosic form β-D-glucuronate is found in the glycosaminoglycans chondroitin sulfate, dermatan sulfate, heparin, heparan sulfate and hyaluronan. It is often sulfated in the C2 position to form 2-O-sulfo-β-D-glucuronate.

Chemical Formula: C6H9O7

Molecular Weight: 193.13 Daltons

Monoisotopic Molecular Weight: 194.0426526757 Daltons

SMILES: C1(O)(C(O)C(O)OC(C(=O)[O-])C(O)1)

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)/p-1/t1-,2-,3+,4-,6+/m0/s1

InChIKey: InChIKey=AEMOLEFTQBMNLQ-QIUUJYRFSA-M

Unification Links: ChEBI:28860 , ChemSpider:10051464 , MetaboLights:MTBLC28860 , PubChem:11877136

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -169.37196 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

UDP-α-D-glucuronate biosynthesis (from myo-inositol) :
D-glucopyranuronate + ATP → α-D-glucuronate 1-phosphate + ADP + H+

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

chondroitin sulfate degradation (metazoa) :
chondroitin sulfate → N-acetyl-β-D-galactosamine + β-D-glucuronate

luteolin triglucuronide degradation :
luteolin 7-O-[β-D-glucuronosyl-(1,2)-β-D-glucuronide]-4'-O-β-D-glucuronide + H2O → luteolin 7-O-β-D-diglucuronide + β-D-glucuronate
luteolin 7-O-β-D-diglucuronide + H2O → luteolin 7-O-β-D-glucuronide + β-D-glucuronate
luteolin 7-O-β-D-glucuronide + H2O → luteolin + β-D-glucuronate + H+

baicalein degradation (hydrogen peroxide detoxification) , baicalein metabolism :
baicalin + H2O → baicalein + D-glucopyranuronate

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

L-ascorbate biosynthesis IV :
UDP-α-D-glucuronate + H2O → D-glucopyranuronate + UDP + H+

UDP-α-D-glucuronate biosynthesis (from myo-inositol) :
myo-inositol + oxygen → D-glucopyranuronate + H+ + H2O

wogonin metabolism :
wogonin 7-O-β-D-glucuronate + H2O → wogonin + D-glucopyranuronate

Not in pathways:
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
D-glucurono-6,3-lactone + H2O → D-glucopyranuronate + H+
oroxylin A 7-O-β-D-glucuronate + H2O → oroxylin A + D-glucopyranuronate
mycophenolic acid O-acyl-glucuronide + H2O → mycophenolate + D-glucopyranuronate + H+
3-D-glucuronosyl-N2-,6-disulo-β-D-glucosamine + H2O → D-glucopyranuronate + N,6-O-disulfo-D-glucosamine
D-Glucurono-6,2-lactone + H2O → D-glucopyranuronate + H+
p-nitrophenyl-α-D-glucuronide + H2O → D-glucopyranuronate + 4-nitrophenol + H+


a protopanaxatriol-type ginsenoside with two glycosyl residues at position 6 + 2 H2O → a protopanaxatriol-type ginsenoside with no glycosidic modification at position 6 + a monosaccharide + D-glucopyranose
a protopanaxadiol-type ginsenoside with two glycosyl residues at position 20 + H2O → a protopanaxadiol-type ginsenoside with a single glucosyl residue at position 20 + a monosaccharide


a thioglucoside + H2O → a sugar + a thiol
a sugar phosphate + H2O → a sugar + phosphate
glycosyl-N-acylsphingosine + H2O → a ceramide + a sugar

3,3'-thiodipropionate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropionate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+


an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
a 1-lysophosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-β-D-galactosyl-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate


an N-acetyl-β-D-galactosalaminyl-[glycan] + H2O → a glycan + N-acetyl-β-D-galactosamine

Reactions known to both consume and produce the compound:

β-D-glucuronide and D-glucuronate degradation , D-glucuronate degradation I , D-glucuronate degradation II , L-ascorbate biosynthesis IV :
D-glucopyranuronatealdehydo-D-glucuronate

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
a D-hexose + ATP = D-hexose 6-phosphate + ADP + H+
phosphoramidate + a D-hexose = an α-hexose 1-phosphate + ammonium


a protopanaxatriol-type ginsenoside with two glycosyl residues at position 6 + H2O = a protopanaxatriol-type ginsenoside with a single glucosyl at position 6 + a monosaccharide


eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
an aldehyde + pyrroloquinoline quinone + H2O = a carboxylate + pyrroloquinoline quinol + H+
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized electron acceptor + H2O = a carboxylate + a reduced electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

In Transport reactions:
D-glucuronate[periplasmic space] + H+[periplasmic space]D-glucuronate[cytosol] + H+[cytosol] ,
a monosaccharide[extracellular space] + ATP + H2O ↔ a monosaccharide[cytosol] + ADP + phosphate ,
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[out] → a [PTS enzyme I]-L-histidine + a sugar phosphate[in]

Enzymes activated by β-D-glucuronate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: D-mannonate dehydratase [RobertBaudouy73]

Credits:
Created 28-Jul-2010 by Caspi R , SRI International


References

Casu89: Casu, B. (1989). "in Heparin: Chemical and Biological Properties, Clinical Applications." Lane, D. A., and Lindahl, U., Eds, pp 25-49, CRC Press, Boca Raton, FL.

Gatti79: Gatti, G., Casu, B., Hamer, G. K., Pelin, A. S. (1979). Macromolecules 12:1001-1007.

Girish07: Girish KS, Kemparaju K (2007). "The magic glue hyaluronan and its eraser hyaluronidase: a biological overview." Life Sci 80(21);1921-43. PMID: 17408700

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Murphy04: Murphy KJ, Merry CL, Lyon M, Thompson JE, Roberts IS, Gallagher JT (2004). "A new model for the domain structure of heparan sulfate based on the novel specificity of K5 lyase." J Biol Chem 279(26);27239-45. PMID: 15047699

RobertBaudouy73: Robert-Baudouy JM, Stoeber FR (1973). "[Purification and properties of D-mannonate hydrolyase from Escherichia coli K12]." Biochim Biophys Acta 1973;309(2);473-85. PMID: 4581499

Rosenberg97: Rosenberg RD, Shworak NW, Liu J, Schwartz JJ, Zhang L (1997). "Heparan sulfate proteoglycans of the cardiovascular system. Specific structures emerge but how is synthesis regulated?." J Clin Invest 99(9);2062-70. PMID: 9151776

Trowbridge02: Trowbridge JM, Gallo RL (2002). "Dermatan sulfate: new functions from an old glycosaminoglycan." Glycobiology 12(9);117R-25R. PMID: 12213784


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sun Nov 23, 2014, BIOCYC13A.