Isopropyl beta-D-thiogalactopyranoside

Identification

Name
Isopropyl beta-D-thiogalactopyranoside
Accession Number
DB01862  (EXPT01924)
Type
Small Molecule
Groups
Experimental
Description

A non-metabolizable galactose analog that induces expression of the LAC operon. [PubChem]

Structure
Thumb
Synonyms
  • IPTG
  • isopropyl thiogalactoside
  • isopropyl β-D-1-thiogalactopyranoside
  • isopropyl β-D-thiogalactopyranoside
  • isopropyl β-D-thiogalactoside
  • isopropyl-β-D-thiogalactopyranoside
  • isopropyl-β-D-thiogalactoside
Categories
UNII
X73VV2246B
CAS number
367-93-1
Weight
Average: 238.301
Monoisotopic: 238.087494376
Chemical Formula
C9H18O5S
InChI Key
BPHPUYQFMNQIOC-NXRLNHOXSA-N
InChI
InChI=1S/C9H18O5S/c1-4(2)15-9-8(13)7(12)6(11)5(3-10)14-9/h4-13H,3H2,1-2H3/t5-,6+,7+,8-,9+/m1/s1
IUPAC Name
(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(propan-2-ylsulfanyl)oxane-3,4,5-triol
SMILES
[H][C@]1(CO)O[C@@]([H])(SC(C)C)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBeta-galactosidaseNot AvailableEscherichia coli (strain K12)
UGalactoside O-acetyltransferaseNot AvailableEscherichia coli (strain K12)
ULactose operon repressorNot AvailableEscherichia coli (strain K12)
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
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
656894
PubChem Substance
46506884
ChemSpider
571154
BindingDB
192770
ChEBI
61448
HET
IPT
PDB Entries
1jyx / 1kru / 1lbh / 1na0 / 1na3 / 1px4 / 1tlf / 2p9h / 3dyo / 3i3d
show 11 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)121 °CPhysProp
logP-1.26HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility128.0 mg/mLALOGPS
logP-1.1ALOGPS
logP-1ChemAxon
logS-0.27ALOGPS
pKa (Strongest Acidic)12.48ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.06 m3·mol-1ChemAxon
Polarizability23.79 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5503
Blood Brain Barrier-0.5869
Caco-2 permeable-0.7098
P-glycoprotein substrateNon-substrate0.5845
P-glycoprotein inhibitor INon-inhibitor0.8702
P-glycoprotein inhibitor IINon-inhibitor0.9685
Renal organic cation transporterNon-inhibitor0.8938
CYP450 2C9 substrateNon-substrate0.7949
CYP450 2D6 substrateNon-substrate0.8366
CYP450 3A4 substrateNon-substrate0.5667
CYP450 1A2 substrateNon-inhibitor0.8567
CYP450 2C9 inhibitorNon-inhibitor0.8804
CYP450 2D6 inhibitorNon-inhibitor0.9102
CYP450 2C19 inhibitorNon-inhibitor0.8526
CYP450 3A4 inhibitorNon-inhibitor0.879
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.852
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.9212
BiodegradationNot ready biodegradable0.6263
Rat acute toxicity1.7297 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9853
hERG inhibition (predictor II)Non-inhibitor0.9239
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-MS (4 TMS)GC-MSsplash10-014i-1951000000-f57f9ec1838cc25f9520
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as thioglycosides. These are glycoside in which a sugar group is bonded through one carbon to another group via a S-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Thioglycosides
Alternative Parents
Oxanes / Monosaccharides / Monothioacetals / Secondary alcohols / Sulfenyl compounds / Polyols / Oxacyclic compounds / Primary alcohols / Hydrocarbon derivatives
Substituents
S-glycosyl compound / Oxane / Monosaccharide / Monothioacetal / Secondary alcohol / Oxacycle / Organoheterocyclic compound / Sulfenyl compound / Polyol / Hydrocarbon derivative
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
S-glycosyl compound (CHEBI:61448)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Not Available
Gene Name
lacZ
Uniprot ID
P00722
Uniprot Name
Beta-galactosidase
Molecular Weight
116482.045 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Galactoside o-acetyltransferase activity
Specific Function
May assist cellular detoxification by acetylating non-metabolizable pyranosides, thereby preventing their reentry into the cell.
Gene Name
lacA
Uniprot ID
P07464
Uniprot Name
Galactoside O-acetyltransferase
Molecular Weight
22798.89 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Transcriptional repressor activity, bacterial-type rna polymerase core promoter proximal region sequence-specific binding
Specific Function
Repressor of the lactose operon. Binds allolactose as an inducer.
Gene Name
lacI
Uniprot ID
P03023
Uniprot Name
Lactose operon repressor
Molecular Weight
38589.815 Da

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:10