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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentGluconolactones
Alternative Parents
Substituents
  • Gluconolactone
  • Delta_valerolactone
  • Delta valerolactone
  • Oxane
  • Secondary alcohol
  • Polyol
  • Lactone
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
Pathways
PathwayCategorySMPDB ID
Pentose Phosphate PathwayMetabolicSMP00031
Glucose-6-phosphate dehydrogenase deficiencyDiseaseSMP00518
Ribose-5-phosphate isomerase deficiencyDiseaseSMP00519
Transaldolase deficiencyDiseaseSMP00520
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6673
Blood Brain Barrier+0.5748
Caco-2 permeable-0.8709
P-glycoprotein substrateNon-substrate0.6469
P-glycoprotein inhibitor INon-inhibitor0.9477
P-glycoprotein inhibitor IINon-inhibitor0.9759
Renal organic cation transporterNon-inhibitor0.8928
CYP450 2C9 substrateNon-substrate0.8421
CYP450 2D6 substrateNon-substrate0.8852
CYP450 3A4 substrateNon-substrate0.6784
CYP450 1A2 substrateNon-inhibitor0.9831
CYP450 2C9 substrateNon-inhibitor0.9724
CYP450 2D6 substrateNon-inhibitor0.9668
CYP450 2C19 substrateNon-inhibitor0.9771
CYP450 3A4 substrateNon-inhibitor0.9594
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.98
Ames testNon AMES toxic0.5908
CarcinogenicityNon-carcinogens0.9631
BiodegradationReady biodegradable0.9489
Rat acute toxicity1.0920 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9764
hERG inhibition (predictor II)Non-inhibitor0.9507
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 Solubility586.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.78 m3·mol-1ChemAxon
Polarizability15.63 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
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

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