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Record Information
Version1.0
Creation Date2016-09-30 22:19:55 UTC
Update Date2020-05-21 16:29:05 UTC
BMDB IDBMDB0000127
Secondary Accession Numbers
  • BMDB00127
Metabolite Identification
Common NameD-Glucuronic acid
DescriptionD-Glucuronic acid, also known as glcaa or D-glucuronate, 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. D-Glucuronic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Glucuronic acid exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
GlcAaChEBI
GlcAalphaChEBI
D-GlucuronateGenerator
alpha-D-Glucopyranuronic acidHMDB
alpha-D-Glucuronic acidHMDB
D-(+)-GlucuronateHMDB
D-(+)-Glucuronic acidHMDB
GCUHMDB
GlucosiduronateHMDB
Glucosiduronic acidHMDB
GlucuronateHMDB
Glucuronic acidHMDB
D-Glucopyranuronic acidHMDB
alpha-D-Glucopyranosyluronic acidHMDB
α-D-Glucopyranosyluronic acidHMDB
α-D-Glucopyranuronic acidHMDB
Chemical FormulaC6H10O7
Average Molecular Weight194.1394
Monoisotopic Molecular Weight194.042652674
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number6556-12-3
SMILESNot Available
InChI Identifier
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
InChI KeyAEMOLEFTQBMNLQ-WAXACMCWSA-N
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlucuronic 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point143 - 144 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility485 mg/mLNot Available
LogP-2.57HANSCH,C ET AL. (1995)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Lysosome
Biospecimen Locations
  • Blood
  • Kidney
  • Liver
  • Milk
  • Placenta
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Sub/clinical ketosis
details
HMDB IDHMDB0000127
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021897
KNApSAcK IDC00001123
Chemspider ID392615
KEGG Compound IDC00191
BioCyc IDNot Available
BiGG ID34196
Wikipedia LinkGlucuronic acid
METLIN ID161
PubChem Compound444791
PDB IDNot Available
ChEBI ID42717
References
Synthesis ReferenceHamayasu, 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)Not Available
General References
  1. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.

Enzymes

General function:
Involved in chondroitin-glucuronate 5-epimerase activity
Specific function:
Converts D-glucuronic acid to L-iduronic acid (IdoUA) residues.
Gene Name:
DSE
Uniprot ID:
P0C2H4
Molecular weight:
109725.0
General function:
Involved in hyalurononglucosaminidase activity
Specific function:
Hydrolyzes high molecular weight hyaluronic acid to produce an intermediate-sized product which is further hydrolyzed by sperm hyaluronidase to give small oligosaccharides. Displays very low levels of activity. Associates with and negatively regulates MST1R (By similarity).
Gene Name:
HYAL2
Uniprot ID:
Q8SQG8
Molecular weight:
53881.0
General function:
Involved in hyalurononglucosaminidase activity
Specific function:
May have a role in promoting tumor progression. May block the TGFB1-enhanced cell growth (By similarity).
Gene Name:
HYAL1
Uniprot ID:
Q5E985
Molecular weight:
50508.0
General function:
Involved in inositol oxygenase activity
Specific function:
Not Available
Gene Name:
MIOX
Uniprot ID:
A7MBE4
Molecular weight:
32973.0
Reactions
Myoinositol + Oxygen → D-Glucuronic acid + Waterdetails
General function:
Not Available
Specific function:
Plays an important role in the degradation of dermatan and keratan sulfates.
Gene Name:
GUSB
Uniprot ID:
A3KMY8
Molecular weight:
74470.0
Reactions
Isovalerylglucuronide + Water → D-Glucuronic acid + Alcoholdetails