Human Metabolome Database Version 3.5

Showing metabocard for D-Glucurono-6,3-lactone (HMDB06355)

Record Information
Version 3.5
Creation Date 2007-05-22 19:45:51 -0600
Update Date 2013-02-08 17:14:48 -0700
HMDB ID HMDB06355
Secondary Accession Numbers None
Metabolite Identification
Common Name D-Glucurono-6,3-lactone
Description D-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H8O6
Average Molecular Weight 176.1241
Monoisotopic Molecular Weight 176.032087988
IUPAC Name (3R,3aR,5R,6R,6aR)-3,5,6-trihydroxy-hexahydrofuro[3,2-b]furan-2-one
Traditional IUPAC Name (3R,3aR,5R,6R,6aR)-3,5,6-trihydroxy-tetrahydro-3H-furo[3,2-b]furan-2-one
CAS Registry Number 32449-92-6
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 Key OGLCQHRZUSEXNB-WHDMSYDLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteropolycyclic Compounds
Class Furofurans
Sub Class Isosorbides
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • Carboxylic Acid Ester
  • Gamma Butyrolactone
  • Hemiacetal
  • Lactone
  • Oxolane
  • Secondary Alcohol
Direct Parent Isosorbides
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 177.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 257 mg/mL at 21 °C Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1010 g/L ALOGPS
LogP -1.93 ALOGPS
LogP -1.9 ChemAxon
LogS 0.76 ALOGPS
pKa (strongest acidic) 11.14 ChemAxon
pKa (strongest basic) -4 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 96.22 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 32.3 ChemAxon
Polarizability 14.37 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Endoplasmic reticulum
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023903
KNApSAcK ID Not Available
Chemspider ID 2006482 Link_out
KEGG Compound ID C02670 Link_out
BioCyc ID CPD-526 Link_out
BiGG ID 2216733 Link_out
Wikipedia Link D-glucuronic acid Link_out
NuGOwiki Link HMDB06355 Link_out
Metagene Link HMDB06355 Link_out
METLIN ID Not Available
PubChem Compound 2724333 Link_out
PDB ID Not Available
ChEBI ID 18268 Link_out
References
Synthesis Reference Tsuchioka, 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 Link_out

Enzymes
Name: 4-trimethylaminobutyraldehyde dehydrogenase
Reactions:
D-Glucurono-6,3-lactone + NAD + Water unknown Glucaric acid + NADH + Hydrogen Ion details
Gene Name: ALDH9A1
Uniprot ID: P49189 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-aminoadipic semialdehyde dehydrogenase
Reactions:
D-Glucurono-6,3-lactone + NAD + Water unknown Glucaric acid + NADH + Hydrogen Ion details
Gene Name: ALDH7A1
Uniprot ID: P49419 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 1 member A3
Reactions: Not Available
Gene Name: ALDH1A3
Uniprot ID: P47895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, mitochondrial
Reactions:
D-Glucurono-6,3-lactone + NAD + Water unknown Glucaric acid + NADH + Hydrogen Ion details
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty aldehyde dehydrogenase
Reactions:
D-Glucurono-6,3-lactone + NAD + Water unknown Glucaric acid + NADH + Hydrogen Ion details
Gene Name: ALDH3A2
Uniprot ID: P51648 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase X, mitochondrial
Reactions:
D-Glucurono-6,3-lactone + NAD + Water unknown Glucaric acid + NADH + Hydrogen Ion details
Gene Name: ALDH1B1
Uniprot ID: P30837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dermatan-sulfate epimerase
Reactions: Not Available
Gene Name: DSE
Uniprot ID: Q9UL01 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D-glucuronyl C5-epimerase
Reactions: Not Available
Gene Name: GLCE
Uniprot ID: O94923 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA