Gluconolactone

Identification

Name
Gluconolactone
Accession Number
DB04564  (EXPT02023)
Type
Small Molecule
Groups
Approved, Experimental
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
Synonyms
  • 1,5-D-gluconolactone
  • 1,5-Gluconolactone
  • D-gluconic acid delta-lactone
  • D-glucono-1,5-lactone
  • D-threo-Aldono-1,5-lactone
  • delta-gluconolactone
  • GDL
  • Gluconic acid lactone
  • Glucono delta-lactone
  • Glucono-delta-lactone
External IDs
E-575 / INS NO.575 / INS-575 / NSC-34393
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
RenacidinGluconolactone (.198 g/100mL) + Citric Acid (6.6 g/100mL) + Magnesium carbonate (3.376 g/100mL)SolutionIrrigationUnited Guardian, Inc.1991-01-012018-06-01Us
RenacidinGluconolactone (.198 g/100mL) + Citric Acid (6.602 g/100mL) + Magnesium carbonate (3.268 g/100mL)SolutionIrrigationUnited Guardian, Inc.2016-02-01Not applicableUs
Categories
UNII
WQ29KQ9POT
CAS number
90-80-2
Weight
Average: 178.14
Monoisotopic: 178.047738052
Chemical Formula
C6H10O6
InChI Key
PHOQVHQSTUBQQK-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

Pharmacology

Indication
Not Available
Structured Indications
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULactase-phlorizin hydrolaseNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Pentose Phosphate PathwayMetabolic
Transaldolase deficiencyDisease
Glucose-6-phosphate dehydrogenase deficiencyDisease
Ribose-5-phosphate isomerase deficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00150
KEGG Drug
D04332
KEGG Compound
C00198
PubChem Compound
7027
PubChem Substance
46506698
ChemSpider
6760
BindingDB
50366565
ChEBI
16217
ChEMBL
CHEMBL1200829
HET
LGC
Wikipedia
Gluconolactone
PDB Entries
1e6x / 2e40 / 2vwg / 2w39 / 3azz / 3eqo / 3vif / 4ynu / 4zlg / 4zob
show 1 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SolutionIrrigation
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.9724
CYP450 2D6 inhibitorNon-inhibitor0.9668
CYP450 2C19 inhibitorNon-inhibitor0.9771
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0932000000-0b9d34fd1930d30adac9
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-005a-0920000000-48470ef74f46934597a0
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014j-0950000000-483acf515b56ae5dc886
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0fvi-1952000000-f92fb779cdb5daa45f09
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-0fvi-1952000000-f92fb779cdb5daa45f09
MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)LC-MS/MSsplash10-001i-5900000000-443ab6dcdad04641cb49
MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)LC-MS/MSsplash10-0avl-9000000000-5aba2e27767b74e7e315
MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)LC-MS/MSsplash10-052f-9000000000-081648ead7bc8b21d941
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Gluconolactones
Alternative Parents
Delta valerolactones / Oxanes / Secondary alcohols / Carboxylic acid esters / Polyols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Primary alcohols / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Gluconolactone / Delta valerolactone / Delta_valerolactone / Oxane / Carboxylic acid ester / Lactone / Secondary alcohol / Organoheterocyclic compound / Monocarboxylic acid or derivatives / Oxacycle
show 8 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
aldono-1,5-lactone, gluconolactone (CHEBI:16217)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transferase activity
Specific Function
LPH splits lactose in the small intestine.
Gene Name
LCT
Uniprot ID
P09848
Uniprot Name
Lactase-phlorizin hydrolase
Molecular Weight
218584.77 Da
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:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:43