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Record Information

Version

2.0

Creation Date

2012-05-31 14:04:13 -0600

Update Date

2015-09-13 12:56:13 -0600

Secondary Accession Numbers

ECMDB04073

Identification

Name:

D-Glucuronic acid

Description

Glucuronic acid is a carboxylic acid that has the structure of a glucose molecule that has had its sixth carbon atom (of six total) oxidized. The salts of glucuronic acid are known as glucuronates. Glucuronic acid is highly soluble in water.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

a-D-Glucopyranuronate
a-D-Glucopyranuronic acid
a-D-Glucuronate
a-D-Glucuronic acid
a-delta-Glucopyranuronate
a-delta-Glucopyranuronic acid
a-delta-Glucuronate
a-delta-Glucuronic acid
a-δ-Glucopyranuronate
a-δ-Glucopyranuronic acid
a-δ-Glucuronate
a-δ-Glucuronic acid
Alpha-D-Glucopyranuronate
Alpha-D-Glucopyranuronic acid
Alpha-D-Glucuronate
Alpha-D-Glucuronic acid
Alpha-delta-Glucopyranuronate
Alpha-delta-Glucopyranuronic acid
Alpha-delta-Glucuronate
Alpha-delta-Glucuronic acid
D-(+)-Glucuronate
D-(+)-Glucuronic acid
D-Glucopyranuronate
D-glucopyranuronic acid
D-Glucuronate
D-Glucuronic acid
Delta-(+)-Glucuronate
Delta-(+)-Glucuronic acid
Delta-Glucuronate
Delta-Glucuronic acid
GCU
GlcA
Glucosiduronate
Glucosiduronic acid
Glucuronate
Glucuronic acid
α-D-Glucopyranuronate
α-D-Glucopyranuronic acid
α-D-Glucuronate
α-D-Glucuronic acid
α-δ-Glucopyranuronate
α-δ-Glucopyranuronic acid
α-δ-Glucuronate
α-δ-Glucuronic acid
δ-(+)-Glucuronate
δ-(+)-Glucuronic acid
δ-Glucuronate
δ-Glucuronic acid

Chemical Formula:

C₆H₁₀O₇

Weight:

Average: 194.1394
Monoisotopic: 194.042652674

InChI Key:

AEMOLEFTQBMNLQ-WAXACMCWSA-N

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

CAS number:

6556-12-3

IUPAC Name:

(2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid

Traditional IUPAC Name:

glucuronic acid

SMILES:

O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents

Substituents

Glucuronic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Pyran
Monosaccharide
Oxane
Hemiacetal
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucopyranuronic acid (CHEBI:42717 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

143-144 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	485 mg/mL [HMP experimental]	PhysProp
LogP:	-2.57 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	295 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-2.6	ChemAxon
logS	0.18	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.79 m³·mol⁻¹	ChemAxon
Polarizability	16.32 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

D-Glucuronic acid <> D-Fructuronate
Water + beta-D-Glucuronoside + beta-D-Glucuronoside <> D-Glucuronic acid + Alcohol + Alcohol
Bilirubin diglucuronide + 2 Water + 3 Reduced acceptor <> D-Urobilinogen +2 D-Glucuronic acid +3 Acceptor
G13040 + Water <> G09660 + D-Glucuronic acid
Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-beta-D-glucuronide + Water <> Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide] + D-Glucuronic acid
SN38 glucuronide + Water <> SN-38 + D-Glucuronic acid
Water + a β-D-glucuronoside > D-Glucuronic acid + an alcohol
A beta-D-glucuronoside + Water > D-Glucuronic acid + an alcohol
D-Glucuronic acid > D-Fructuronate
Bilirubin diglucuronide + Water > D-Glucuronic acid + Ribitol + Ribitol

SMPDB Pathways:

Starch and sucrose metabolism

PW000941

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520
Ascorbate and aldarate metabolism ec00053
Drug metabolism - other enzymes ec00983
Flavone and flavonol biosynthesis ec00944
Glycosaminoglycan degradation ec00531
Inositol phosphate metabolism ec00562
Metabolic pathways eco01100
Pentose and glucuronate interconversions ec00040
Porphyrin and chlorophyll metabolism ec00860
Starch and sucrose metabolism ec00500

EcoCyc Pathways:

β-D-glucuronide and D-glucuronate degradation GLUCUROCAT-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6s-5900000000-4145d7dbe91803d8047f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-000l-6242950000-7b610ed98440b47c2a32	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0h9c-7900000000-36121a46a2890d86232e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0ab9-9000000000-8c30084b43ecb0cf7818	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0nti-9600000000-4b612e578cdaf7741845	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0abi-9100000000-d11d1ca4f89a0e4fd2c3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-da8418e381341d813f7e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9000000000-20adab7c4933c484d638	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-9000000000-f25129f7a6ec64681c54	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0fk9-9700000000-1c1e9d5073121d3855c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0900000000-580b96de2b78621ac645	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056s-1900000000-5b29218582cf3ee829fd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9400000000-2aa876e0cbcc0ef3bddf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-0900000000-5e77c9eef959f8dfe0bf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0035-3900000000-97b32d589162947b3a11	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-23aa5a5d3545ff8b0f90	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-2877a7e6d3ecd32cf172	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-7900000000-d748e59637b495442c9e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9100000000-40ac961f184de816ed86	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-3900000000-64f3d0eb26f7bc8ca624	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a73-9300000000-329488f791f643b1c308	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-474e82a5911096bc3b39	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Carpenter PC, Mattox VR: Isolation, determination of structure and synthesis of the acid-labile conjugate of aldosterone. Biochem J. 1976 Jul 1;157(1):1-14. Pubmed: 962850
Jowett TP, Slater JD: A radioimmunoassay for the measurement of tetrahydroaldosterone 3-glucosiduronic acid in human plasma. Clin Chim Acta. 1981 Jan 22;109(2):133-44. Pubmed: 7193539
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Karasawa E: [Supplementary findings on urinary glucuronic acid excretion in pediatrics. I. Total glucuronic acid in 24-hour urine of normal infants determined by the modified Fishman's method with NaBH4] Nippon Shonika Gakkai Zasshi. 1968 Aug 1;72(8):1122-7. Pubmed: 5755643
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Little JM, St Pyrek J, Lester R: Hepatic metabolism of 3 alpha-hydroxy-5 beta-etianic acid (3 alpha-hydroxy-5 beta-androstan-17 beta-carboxylic acid) in the adult rat. J Clin Invest. 1983 Jan;71(1):73-80. Pubmed: 6848561
McDonagh AF, Palma LA, Lauff JJ, Wu TW: Origin of mammalian biliprotein and rearrangement of bilirubin glucuronides in vivo in the rat. J Clin Invest. 1984 Sep;74(3):763-70. Pubmed: 6470139
Murano PS, Robichaud VY, Webb RE: Urinary excretion of sulfate and glucuronate conjugates in a free living population of adult males. Bull Environ Contam Toxicol. 1989 Jul;43(1):13-6. Pubmed: 2758129
Nishida T, Gatmaitan Z, Roy-Chowdhry J, Arias IM: Two distinct mechanisms for bilirubin glucuronide transport by rat bile canalicular membrane vesicles. Demonstration of defective ATP-dependent transport in rats (TR-) with inherited conjugated hyperbilirubinemia. J Clin Invest. 1992 Nov;90(5):2130-5. Pubmed: 1430236
Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9. Pubmed: 16598814
Raju U, Sklarew RJ, Post J, Levitz M: Steroid metabolism in human breast cancer cell lines. Steroids. 1978 Dec;32(5):669-80. Pubmed: 734701
Schmitt G, Aderjan R, Keller T, Wu M: Ethyl glucuronide: an unusual ethanol metabolite in humans. Synthesis, analytical data, and determination in serum and urine. J Anal Toxicol. 1995 Mar-Apr;19(2):91-4. Pubmed: 7769794
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
Stearns RA, Miller RR, Doss GA, Chakravarty PK, Rosegay A, Gatto GJ, Chiu SH: The metabolism of DuP 753, a nonpeptide angiotensin II receptor antagonist, by rat, monkey, and human liver slices. Drug Metab Dispos. 1992 Mar-Apr;20(2):281-7. Pubmed: 1352222
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Hamayasu, Kenichi; Tadokoro, Hiroki; Kishino, Eriko; Ito, Tetsuya; Fujita, Koki; Hara, Kozo. Preparation of glucuronic acid and/or glucuronolactone from sucrose. PCT Int. Appl. (2006), 21pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	42717
HMDB ID	HMDB00127
Pubchem Compound ID	444791
Kegg ID	C00191
ChemSpider ID	392615
Wikipedia	GCU
BioCyc ID	GLUCURONATE
EcoCyc ID	GLUCURONATE
Ligand Expo	GCU

Enzymes

Protein Details

1. Beta-glucuronidase

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: A beta-D-glucuronoside + H(2)O = D-glucuronate + an alcohol
Gene Name:: uidA
Uniprot ID:: P05804
Molecular weight:: 68447

Reactions

A beta-D-glucuronoside + H(2)O = D-glucuronate + an alcohol.

Protein Details

2. 2-keto-3-deoxygluconate permease

General function:: Involved in 2-keto-3-deoxygluconate:hydrogen symporter activity
Specific function:: The 2-keto-3-deoxygluconate permease transports the degraded pectin products into the bacterial cell, where they serve as carbon and energy sources. This is a hydrogen coupled transport system
Gene Name:: kdgT
Uniprot ID:: P0A712
Molecular weight:: 33669

Protein Details

3. Uronate isomerase

General function:: Involved in glucuronate isomerase activity
Specific function:: D-glucuronate = D-fructuronate
Gene Name:: uxaC
Uniprot ID:: P0A8G3
Molecular weight:: 53987

Reactions

D-glucuronate = D-fructuronate.
D-galacturonate = D-tagaturonate.

Transporters

Protein Details

1. 2-keto-3-deoxygluconate permease

General function:: Involved in 2-keto-3-deoxygluconate:hydrogen symporter activity
Specific function:: The 2-keto-3-deoxygluconate permease transports the degraded pectin products into the bacterial cell, where they serve as carbon and energy sources. This is a hydrogen coupled transport system
Gene Name:: kdgT
Uniprot ID:: P0A712
Molecular weight:: 33669

Protein Details

2. Hexuronate transporter

General function:: Involved in transporter activity
Specific function:: Aldohexuronate transport system
Gene Name:: exuT
Uniprot ID:: P0AA78
Molecular weight:: 51571

Protein Details

3. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

4. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

5. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

6. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

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D-Glucuronic acid (M2MDB000596)

Structure for #<Compound:0xa0004f4c>

Enzymes

Reactions

Reactions

Transporters