Identification

Name
Isatin
Accession Number
DB02095  (EXPT01935)
Type
Small Molecule
Groups
Experimental
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
Categories
UNII
82X95S7M06
CAS number
91-56-5
Weight
Average: 147.1308
Monoisotopic: 147.032028409
Chemical Formula
C8H5NO2
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAmine oxidase [flavin-containing] BNot 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
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

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

US4256639
General References
Not Available
External Links
Human Metabolome Database
HMDB61933
KEGG Compound
C11129
PubChem Compound
7054
PubChem Substance
46507369
ChemSpider
6787
BindingDB
11022
ChEBI
27539
ChEMBL
CHEMBL326294
HET
ISN
Wikipedia
Isatin
PDB Entries
1oja / 2bk5 / 2xfp / 5oji / 5ph6

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)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
SpectrumSpectrum TypeSplash Key
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
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-b7740f917ea3a513cccf
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-7cc1e59d64b0f9fe75c7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9200000000-7222eca5f15462cb52d6
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-9d8ae3e3d93ebbae650e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-5f853d2ccc4bbe2b3a89
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-4d14e90a2ccd915ec028
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-1900000000-efd2670c6d91416ca123
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001l-3900000000-a768411b3bdce1e8bbf7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0f89-3900000000-00d17037a416b9858a30
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fc0-7900000000-b2e65fbe547a142b1b3e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001j-0900000000-6129e468197154787423
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01ot-6900000000-e172235ae1d7d5980b78
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0g5d-9600000000-3abf3b0049a56410c636
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014l-9100000000-0fb3353ec5204cb4b15c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ik9-9000000000-82722063406d135a28ca

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolines
Direct Parent
Indolines
Alternative Parents
Aryl ketones / Benzenoids / Vinylogous amides / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Dihydroindole / Aryl ketone / Benzenoid / Vinylogous amide / Carboxamide group / Ketone / Lactam / Secondary carboxylic acid amide / Carboxylic acid derivative / Azacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
indoledione (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...
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...
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 November 09, 2017 03:09