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Record Information
Version3.6
Creation Date2007-05-23 01:45:51 UTC
Update Date2013-02-09 00:14:48 UTC
HMDB IDHMDB06355
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Glucurono-6,3-lactone
DescriptionD-glucurono-6,3-lactone participates in ascorbate and aldarate metabolism. D-glucurono-6,3-lactone is produced by the reaction between D-glucaric acid and the enzyme, aldehyde dehydrogenase (NAD+) [EC: 1.2.1.3].
Structure
Thumb
Synonyms
  1. D-Glucurone
  2. D-Glucuronic acid
  3. D-Glucuronic acid lactone (van)
  4. D-Glucurono-3,6-lactone
  5. D-Glucuronolactone
  6. Dicurone
  7. Glucofuranurono-6,3-lactone
  8. Glucoxy
  9. Glucurolactone
  10. Glucuron
  11. Glucurone
  12. Glucuronic acid lactone
  13. Glucuronolactone (van)
  14. Glucuronosan
  15. Gluronsan
  16. Glycurone
  17. Guronsan (van)
  18. Reulatt S.S.
Chemical FormulaC6H8O6
Average Molecular Weight176.1241
Monoisotopic Molecular Weight176.032087988
IUPAC Name(3R,3aR,5R,6R,6aR)-3,5,6-trihydroxy-hexahydrofuro[3,2-b]furan-2-one
Traditional Name(3R,3aR,5R,6R,6aR)-3,5,6-trihydroxy-tetrahydro-3H-furo[3,2-b]furan-2-one
CAS Registry Number32449-92-6
SMILES
O[C@@H]1O[C@@H]2[C@@H](O)C(=O)O[C@@H]2[C@H]1O
InChI Identifier
InChI=1S/C6H8O6/c7-1-3-4(12-5(1)9)2(8)6(10)11-3/h1-5,7-9H/t1-,2-,3-,4-,5-/m1/s1
InChI KeyOGLCQHRZUSEXNB-WHDMSYDLSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Heteropolycyclic Compounds
ClassFurofurans
Sub ClassIsosorbides
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • Carboxylic Acid Ester
  • Gamma Butyrolactone
  • Hemiacetal
  • Lactone
  • Oxolane
  • Secondary Alcohol
Direct ParentIsosorbides
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point177.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility257 mg/mL at 21 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1010 g/LALOGPS
logP-1.9ALOGPS
logP-1.9ChemAxon
logS0.76ALOGPS
pKa (Strongest Acidic)11.14ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.3ChemAxon
Polarizability14.37ChemAxon
Spectra
Spectra1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Endoplasmic reticulum
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023903
KNApSAcK IDNot Available
Chemspider ID2006482
KEGG Compound IDC02670
BioCyc IDCPD-526
BiGG ID2216733
Wikipedia LinkD-glucuronic acid
NuGOwiki LinkHMDB06355
Metagene LinkHMDB06355
METLIN IDNot Available
PubChem Compound2724333
PDB IDNot Available
ChEBI ID18268
References
Synthesis ReferenceTsuchioka, Toshiki; Yamaguchi, Tadashi; Yuuen, Kunihiko; Chaen, Hiroto. Process for producing D-glucuronolactone from trehalose via oxidation and hydrolysis. Eur. Pat. Appl
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. DEMOEN P, JANSSEN P, VAN DE KEERE B, ZIVKOVIC D: On the metabolic fate of isoniazide (I.N.H.) and its N2-Dglucuronolactone derivate (I.N.H.G.) (1) in man. Arch Int Pharmacodyn Ther. 1954 Aug 1;98(4):427-36. Pubmed: 13208334

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
D-Glucurono-6,3-lactone + NAD + Water → Glucaric acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
D-Glucurono-6,3-lactone + NAD + Water → Glucaric acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
D-Glucurono-6,3-lactone + NAD + Water → Glucaric acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
D-Glucurono-6,3-lactone + NAD + Water → Glucaric acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
D-Glucurono-6,3-lactone + NAD + Water → Glucaric acid + NADH + Hydrogen Iondetails
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:
Q9UL01
Molecular weight:
109772.235
General function:
Involved in racemase and epimerase activity, acting on carbohydrates and derivatives
Specific function:
Converts D-glucuronic acid residues adjacent to N- sulfate sugar residues to L-iduronic acids
Gene Name:
GLCE
Uniprot ID:
O94923
Molecular weight:
70100.5