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Identification
NameIsatin
Accession NumberDB02095  (EXPT01935)
TypeSmall Molecule
GroupsExperimental
DescriptionIsatin is an indole derivative. The compound was first obtained by Erdman and Laurent in 1841 as a product from the oxidation of Indigo dye by nitric acid and chromic acids. The compound is found in many plants and Schiff bases of Isatin are investigated for their pharmaceutical properties. [Wikipedia]
Structure
Thumb
Synonyms
1H-indole-2,3-dione
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII82X95S7M06
CAS number91-56-5
WeightAverage: 147.1308
Monoisotopic: 147.032028409
Chemical FormulaC8H5NO2
InChI KeyInChIKey=JXDYKVIHCLTXOP-UHFFFAOYSA-N
InChI
InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
IUPAC Name
2,3-dihydro-1H-indole-2,3-dione
SMILES
O=C1NC2=CC=CC=C2C1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indolines. These are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolines
Direct ParentIndolines
Alternative Parents
Substituents
  • Dihydroindole
  • Aryl ketone
  • Benzenoid
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Lactam
  • Ketone
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9944
Caco-2 permeable+0.6443
P-glycoprotein substrateNon-substrate0.8274
P-glycoprotein inhibitor INon-inhibitor0.8426
P-glycoprotein inhibitor IINon-inhibitor0.8273
Renal organic cation transporterNon-inhibitor0.8946
CYP450 2C9 substrateNon-substrate0.8221
CYP450 2D6 substrateNon-substrate0.8111
CYP450 3A4 substrateNon-substrate0.5891
CYP450 1A2 substrateInhibitor0.8026
CYP450 2C9 inhibitorNon-inhibitor0.9332
CYP450 2D6 inhibitorNon-inhibitor0.8689
CYP450 2C19 inhibitorNon-inhibitor0.8833
CYP450 3A4 inhibitorNon-inhibitor0.9776
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7789
Ames testNon AMES toxic0.6182
CarcinogenicityNon-carcinogens0.9499
BiodegradationNot ready biodegradable0.6703
Rat acute toxicity2.0665 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9784
hERG inhibition (predictor II)Non-inhibitor0.9302
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point203 dec °CPhysProp
logP0.83HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.77 mg/mLALOGPS
logP0.89ALOGPS
logP1.6ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)8.93ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.17 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.48 m3·mol-1ChemAxon
Polarizability13.8 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Leandro Baiocchi, “Process for the synthesis of isatin derivatives.” U.S. Patent US4256639, issued July, 1968.

US4256639
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Primary amine oxidase activity
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular Weight:
58762.475 Da

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Primary amine oxidase activity
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular Weight:
58762.475 Da
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23