Identification
- Generic Name
- Isatin
- DrugBank Accession Number
- DB02095
- Background
Isatin is an indole derivative first obtained by Erdman and Laurent in 1841 as an oxidation product of Indigo dye with nitric acid and chromic acids. The compound is found in many plants and Schiff bases of Isatin are have been investigated for pharmaceutical applications.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Isatin (DB02095)
- Weight
- Average: 147.1308
Monoisotopic: 147.032028409 - Chemical Formula
- C8H5NO2
- Synonyms
- 1H-indole-2,3-dione
- External IDs
- NSC-9262
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UAmine oxidase [flavin-containing] B Not Available Humans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Aromatic heteropolycyclic compound / Aryl ketone / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dihydroindole / Hydrocarbon derivative / Ketone
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- indoledione (CHEBI:27539) / a small molecule (ISATIN)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 82X95S7M06
- CAS number
- 91-56-5
- 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
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
- HMDB0061933
- KEGG Compound
- C11129
- PubChem Compound
- 7054
- PubChem Substance
- 46507369
- ChemSpider
- 6787
- BindingDB
- 11022
- ChEBI
- 27539
- ChEMBL
- CHEMBL326294
- ZINC
- ZINC000002047514
- PDBe Ligand
- ISN
- Wikipedia
- Isatin
- PDB Entries
- 1oja / 2bk5 / 2xfp / 5oji / 5ph6 / 5rtf / 6af5 / 6af9 / 6afa / 6afb … show 1 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 203 dec °C PhysProp logP 0.83 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 2.77 mg/mL ALOGPS logP 0.89 ALOGPS logP 1.6 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 9.33 Chemaxon pKa (Strongest Basic) -5.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.17 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 40.48 m3·mol-1 Chemaxon Polarizability 13.8 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9944 Caco-2 permeable + 0.6443 P-glycoprotein substrate Non-substrate 0.8274 P-glycoprotein inhibitor I Non-inhibitor 0.8426 P-glycoprotein inhibitor II Non-inhibitor 0.8273 Renal organic cation transporter Non-inhibitor 0.8946 CYP450 2C9 substrate Non-substrate 0.8221 CYP450 2D6 substrate Non-substrate 0.8111 CYP450 3A4 substrate Non-substrate 0.5891 CYP450 1A2 substrate Inhibitor 0.8026 CYP450 2C9 inhibitor Non-inhibitor 0.9332 CYP450 2D6 inhibitor Non-inhibitor 0.8689 CYP450 2C19 inhibitor Non-inhibitor 0.8833 CYP450 3A4 inhibitor Non-inhibitor 0.9776 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7789 Ames test Non AMES toxic 0.6182 Carcinogenicity Non-carcinogens 0.9499 Biodegradation Not ready biodegradable 0.6703 Rat acute toxicity 2.0665 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9784 hERG inhibition (predictor II) Non-inhibitor 0.9302
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
References
- Igosheva N, Lorz C, O'Conner E, Glover V, Mehmet H: Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. Neurochem Int. 2005 Aug;47(3):216-24. doi: 10.1016/j.neuint.2005.02.011. [Article]
- Panova NG, Zemskova MA, Axenova LN, Medvedev AE: Does isatin interact with rat brain monoamine oxidases in vivo? Neurosci Lett. 1997 Sep 12;233(1):58-60. doi: 10.1016/s0304-3940(97)00597-1. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52