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Identification
NameGluconolactone
Accession NumberDB04564  (EXPT02023)
Typesmall molecule
Groupsexperimental
Description

Gluconolactone is a naturally-occurring food additive used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent. It is a cyclic ester of D-gluconic acid. Pure gluconolactone is a white odorless crystalline powder.

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number90-80-2
WeightAverage: 178.14
Monoisotopic: 178.047738052
Chemical FormulaC6H10O6
InChI KeyPHOQVHQSTUBQQK-SQOUGZDYSA-N
InChI
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
IUPAC Name
(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
SMILES
OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassMonosaccharides
Direct parentGluconolactones
Alternative parentsDelta Valerolactones; Oxanes; Secondary Alcohols; 1,2-Diols; Carboxylic Acid Esters; Primary Alcohols; Polyamines
Substituentsdelta valerolactone; oxane; secondary alcohol; polyol; carboxylic acid ester; lactone; 1,2-diol; polyamine; primary alcohol; carboxylic acid derivative; alcohol
Classification descriptionThis compound belongs to the 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.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.6673
Blood Brain Barrier + 0.5748
Caco-2 permeable - 0.8709
P-glycoprotein substrate Non-substrate 0.6469
P-glycoprotein inhibitor I Non-inhibitor 0.9477
P-glycoprotein inhibitor II Non-inhibitor 0.9759
Renal organic cation transporter Non-inhibitor 0.8928
CYP450 2C9 substrate Non-substrate 0.8421
CYP450 2D6 substrate Non-substrate 0.8852
CYP450 3A4 substrate Non-substrate 0.6784
CYP450 1A2 substrate Non-inhibitor 0.9831
CYP450 2C9 substrate Non-inhibitor 0.9724
CYP450 2D6 substrate Non-inhibitor 0.9668
CYP450 2C19 substrate Non-inhibitor 0.9771
CYP450 3A4 substrate Non-inhibitor 0.9594
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.98
Ames test Non AMES toxic 0.5908
Carcinogenicity Non-carcinogens 0.9631
Biodegradation Ready biodegradable 0.9489
Rat acute toxicity 1.0920 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9764
hERG inhibition (predictor II) Non-inhibitor 0.9507
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubility5.9E+005 mg/L (at 25 °C)MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
water solubility5.86e+02 g/lALOGPS
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 area107.22ChemAxon
rotatable bond count1ChemAxon
refractivity34.78ChemAxon
polarizability15.63ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD04332
KEGG CompoundC00198
PubChem Compound7027
PubChem Substance46506698
ChEBI16217
ChEMBL
HETLGC
WikipediaGluconolactone
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Lactase-phlorizin hydrolase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Lactase-phlorizin hydrolase P09848 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:25