Showing metabocard for Gluconolactone (BMDB0000150)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:20:12 UTC
Update Date2020-05-21 16:28:59 UTC
BMDB IDBMDB0000150
Secondary Accession Numbers
  • BMDB00150
Metabolite Identification
Common NameGluconolactone
DescriptionGluconolactone, also known as GDL (gluconate) or gluconolactone, belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Gluconolactone exists in all living organisms, ranging from bacteria to humans. Gluconolactone participates in a number of enzymatic reactions, within cattle. In particular, Gluconolactone and nadph can be biosynthesized from Beta-D-glucose 6-phosphate and nadp through the action of the enzyme glucose-6-phosphate 1-dehydrogenase. In addition, Gluconolactone and water can be converted into 6-phosphogluconic acid; which is mediated by the enzyme 6-phosphogluconolactonase. In cattle, gluconolactone is involved in the metabolic pathway called the pentose phosphate pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-oneChEBI
1,5-D-GluconolactoneChEBI
1,5-GluconolactoneChEBI
D-AldonolactoneChEBI
D-Gluconic acid delta-lactoneChEBI
D-Gluconic acid lactoneChEBI
D-GluconolactoneChEBI
D-threo-aldono-1,5-LactoneChEBI
delta-D-GluconolactoneChEBI
delta-GluconolactoneChEBI
GlucarolactoneChEBI
Gluconic acid lactoneChEBI
Gluconic delta-lactoneChEBI
Gluconic lactoneChEBI
D-Gluconate delta-lactoneGenerator
D-Gluconate δ-lactoneGenerator
D-Gluconic acid δ-lactoneGenerator
D-Gluconate lactoneGenerator
δ-D-gluconolactoneGenerator
δ-GluconolactoneGenerator
Gluconate lactoneGenerator
Gluconic δ-lactoneGenerator
1,5-delta-GluconolactoneHMDB
3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-oneHMDB
D-(+)-Gluconic acid D-lactoneHMDB
D-(+)-Gluconic acid-delta lactoneHMDB
D-delta-GluconolactoneHMDB
D-Gluconic acid 1,5-lactoneHMDB
D-Gluconic acid D-lactoneHMDB
D-Gluconic acid-1,5-lactoneHMDB
D-Gluconic acid-delta-lactoneHMDB
D-Gluconic delta-lactoneHMDB
D-Glucono-1,5-lactoneHMDB
D-glucono-D-LactoneHMDB
delta-(+)-Gluconic acid D-lactoneHMDB
delta-AldonolactoneHMDB
delta-Gluconic acid 1,5-lactoneHMDB
delta-Gluconic acid D-lactoneHMDB
delta-Gluconic acid lactoneHMDB
delta-Gluconic acid-1,5-lactoneHMDB
delta-Glucono-1,5-lactoneHMDB
FujigluconHMDB
Gluconate, lactoneHMDB
Glucono 1,5-lactoneHMDB
Glucono delta lactoneHMDB
Glucono delta-lactoneHMDB
GDL (Gluconate)MeSH, HMDB
Glucono-delta-lactoneMeSH
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-oneHMDB
D-(+)-Gluconic acid delta-lactoneHMDB
D-(+)-Gluconic acid δ-lactoneHMDB
D-(+)-Glucono-1,5-lactoneHMDB
D-(+)-Glucono-delta-lactoneHMDB
D-(+)-Glucono-δ-lactoneHMDB
D-(+)-Glucose delta-lactoneHMDB
D-(+)-Glucose δ-lactoneHMDB
D-Glucono-delta-lactoneHMDB
D-Glucono-δ-lactoneHMDB
Glucono-δ-lactoneHMDB
GluconolactoneHMDB
LysactoneHMDB
Chemical FormulaC6H10O6
Average Molecular Weight178.14
Monoisotopic Molecular Weight178.047738052
IUPAC Name(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
Traditional Namegluconolactone
CAS Registry Number90-80-2
SMILES
OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1
InChI KeyPHOQVHQSTUBQQK-SQOUGZDYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGluconolactones
Alternative Parents
Substituents
  • Gluconolactone
  • Delta valerolactone
  • Delta_valerolactone
  • Oxane
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point151 - 155 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility590.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.2ALOGPS
logP-2.7ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)11.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.78 m³·mol⁻¹ChemAxon
Polarizability15.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000150
DrugBank IDDB04564
Phenol Explorer Compound IDNot Available
FooDB IDFDB001245
KNApSAcK IDNot Available
Chemspider ID6760
KEGG Compound IDC00198
BioCyc IDGLC-D-LACTONE
BiGG IDNot Available
Wikipedia LinkGluconolactone
METLIN ID353
PubChem Compound7027
PDB IDNot Available
ChEBI ID16217
References
Synthesis ReferenceChu, Lijia. Technology for industrial production of d-gluconolactone. Shipin Kexue (Beijing, China) (1985), 66 13-14.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 6-phosphogluconolactonase
General function:
Carbohydrate transport and metabolism
Specific function:
Hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate.
Gene Name:
PGLS
Uniprot ID:
Q2TBQ8
Molecular weight:
27547.0
Reactions
Gluconolactone + Water → 6-Phosphogluconic aciddetails
Enzyme Details
2. Glucose-6-phosphate 1-dehydrogenase
General function:
Not Available
Specific function:
Catalyzes the rate-limiting step of the oxidative pentose-phosphate pathway, which represents a route for the dissimilation of carbohydrates besides glycolysis.
Gene Name:
G6PD
Uniprot ID:
F1MMK2
Molecular weight:
62414.0
Reactions
Beta-D-Glucose 6-phosphate + NADP → Gluconolactone + NADPHdetails