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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 01:45:51 UTC
Update Date2021-09-14 15:18:57 UTC
HMDB IDHMDB0006355
Secondary Accession Numbers
  • HMDB06355
Metabolite Identification
Common NameD-Glucurono-6,3-lactone
DescriptionD-Glucurono-6,3-lactone belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings. D-Glucurono-6,3-lactone is a very mild and mentholic tasting compound. Glucuronolactone is a naturally occurring substance that is an important structural component of nearly all connective tissues. It is frequently used in energy drinks to increase energy levels and improve alertness, and can also be used to reduce "brain fog" caused by various medical conditions. Glucuronolactone is also found in many plant gums. Glucuronolactone is a white solid odorless compound, soluble in hot and cold water. Its melting point ranges from 176 to 178 °C. The compound can exist in a monocyclic aldehyde form or in a bicyclic hemiacetal (lactol) form. Glucuronolactone is a popular ingredient in energy drinks because it has been shown to be effective at increasing energy levels and improving alertness. Glucuronolactone supplementation also significantly reduces "brain fog" cause by various medical conditions. Although levels of glucuronolactone in energy drinks can far exceed those found in the rest of the diet, glucuronolactone is extremely safe and well tolerated. The European Food Safety Authority (EFSA) has concluded that exposure to glucuronolactone from regular consumption of energy drinks is not a safety concern.[2] The no-observed-adverse-effect level of glucuronolactone is 1000 mg/kg/day. Additionally, according to The Merck Index, glucuronolactone is used as a detoxicant. The liver uses glucose to create glucuronolactone, which inhibits the enzyme B-glucuronidase (metabolizes glucuronides), which should cause blood-glucuronide levels to rise. Glucuronides combines with toxic substances, such as morphine and depot medroxyprogesterone acetate, by converting them to water-soluble glucuronide-conjugates which are excreted in the urine. Higher blood-glucuronides help remove toxins from the body, leading to the claim that energy drinks are detoxifying. Free glucuronic acid (or its self-ester glucuronolactone) has less effect on detoxification than glucose, because the body synthesizes UDP-glucuronic acid from glucose. Therefore, sufficient carbohydrate intake provides enough UDP-glucuronic acid for detoxication, and foods rich in glucose are usually abundant in developed nations. Glucuronolactone is also metabolized to glucaric acid, xylitol, and L-xylulose, and humans may also be able to use glucuronolactone as a precursor for ascorbic acid synthesis.
Structure
Data?1582752382
Synonyms
ValueSource
D-GlucuroneHMDB
D-Glucuronic acidHMDB
D-Glucuronic acid lactoneHMDB
D-Glucurono-3,6-lactoneHMDB
D-GlucuronolactoneHMDB
DicuroneHMDB
Glucofuranurono-6,3-lactoneHMDB
GlucoxyHMDB
GlucurolactoneHMDB
GlucuronHMDB
GlucuroneHMDB
Glucuronic acid lactoneHMDB
GlucuronolactoneHMDB
GlucuronosanHMDB
GluronsanHMDB
GlycuroneHMDB
GuronsanHMDB
Reulatt s.s.HMDB
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
Description Belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurofurans
Sub ClassIsosorbides
Direct ParentIsosorbides
Alternative Parents
Substituents
  • Isosorbide
  • Gamma butyrolactone
  • Monosaccharide
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

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 Area96.22 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.3 m³·mol⁻¹ChemAxon
Polarizability14.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9300000000-ef88fbef84e17d8ed7482017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-008a-4196000000-fcc76e659396761f2af02017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-054o-9300000000-ef88fbef84e17d8ed7482021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-0eff9b2e7506d5b5a56c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1900000000-d1ad382f01f0d42e4d4f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c00-9600000000-e8dfa6f5abce8bd65c802016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-b0d05d510f946ae0a2f02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1900000000-0a93ee6467e8641430d92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r04-9200000000-2b58da5e3c60b6bf452a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-271e9efdb4dfcb70a4032021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-3900000000-a01bf3f9edf2268ead682021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001m-9400000000-0e2503f4cd730a8402fd2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-a0599d18157aa7371b072021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9600000000-3bac8be32b0aac93f8fa2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-8e1918514014e0eade362021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Endoplasmic reticulum
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023903
KNApSAcK IDNot Available
Chemspider ID2006482
KEGG Compound IDC02670
BioCyc IDCPD-526
BiGG ID2216733
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2724333
PDB IDNot Available
ChEBI ID18268
Food Biomarker OntologyNot Available
VMH IDGLAC
MarkerDB IDNot Available
References
Synthesis ReferenceHiroto Chaen, Toshiki Tsuchioka, Tadashi Yamaguchi, Kunihiko Yuuen. Process for producing D-glucuronolactone. 1998, Eur. Pat. Appl. EP0864580A2
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