Identification
NameIsatin
Accession NumberDB02095  (EXPT01935)
TypeSmall Molecule
GroupsExperimental
Description

Isatin 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 IDs NSC-9262
Product Ingredients 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
Categories
UNII82X95S7M06
CAS number91-56-5
WeightAverage: 147.1308
Monoisotopic: 147.032028409
Chemical FormulaC8H5NO2
InChI KeyJXDYKVIHCLTXOP-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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Amine oxidase [flavin-containing] BProteinunknownNot AvailableHumanP27338 details
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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)203 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-b7740f917ea3a513cccfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-7cc1e59d64b0f9fe75c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-7222eca5f15462cb52d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-9d8ae3e3d93ebbae650eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-5f853d2ccc4bbe2b3a89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-4d14e90a2ccd915ec028View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-1900000000-efd2670c6d91416ca123View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001l-3900000000-a768411b3bdce1e8bbf7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f89-3900000000-00d17037a416b9858a30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fc0-7900000000-b2e65fbe547a142b1b3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001j-0900000000-6129e468197154787423View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ot-6900000000-e172235ae1d7d5980b78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0g5d-9600000000-3abf3b0049a56410c636View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-9100000000-0fb3353ec5204cb4b15cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ik9-9000000000-82722063406d135a28caView in MoNA
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
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as indolines. These are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIndoles and derivatives
Direct ParentIndolines
Alternative ParentsAryl ketones / Benzenoids / Vinylogous amides / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
SubstituentsDihydroindole / Aryl ketone / Benzenoid / Vinylogous amide / Carboxamide group / Ketone / Lactam / Secondary carboxylic acid amide / Carboxylic acid derivative / Azacycle
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsindoledione (CHEBI:27539 ) / a small molecule (ISATIN )

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
Uniprot Name:
Amine oxidase [flavin-containing] B
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
Uniprot Name:
Amine oxidase [flavin-containing] B
Molecular Weight:
58762.475 Da
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 17:05