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Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
AGL-2263 is an insulin receptor and insulin-like growth factor (IGF) receptor inhibitor
In Vitro
AGL-2263 (5 μM, for 1 h followed by insulin treatment for 24 h) inhibits IR and insulin could still induce phosphorylation of AKT and ERK1/2 after the IR inhibition. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: Granulosa cells. Concentration: 5 μM. Incubation Time: For 1 h followed by insulin treatment for 24 h. Result: Insulin still induced phosphorylation of AKT and ERK1/2 after IR was inhibited by AGL2263.
Form:Solid
IC50& Target:Insulin receptor
| Canonical Smiles | C1=CC2=C(C=C1C=C(C#N)C(=O)C3=CC(=C(C=C3)O)O)NC(=O)O2 |
|---|---|
| IUPAC Name | (E)-2-(3,4-dihydroxybenzoyl)-3-(2-oxo-3H-1,3-benzoxazol-5-yl)prop-2-enenitrile |
| InChIKey | IUGRBTCJEYEDIY-VZUCSPMQSA-N |
| INCHI | 1S/C17H10N2O5/c18-8-11(16(22)10-2-3-13(20)14(21)7-10)5-9-1-4-15-12(6-9)19-17(23)24-15/h1-7,20-21H,(H,19,23)/b11-5+ |
| Isomeric SMILES | C1=CC2=C(C=C1/C=C(\C#N)/C(=O)C3=CC(=C(C=C3)O)O)NC(=O)O2 |
| PubChem CID | 9818584 |
| MeSH Entry Terms | AGL 2263;AGL-2263;AGL2263 |
| Molecular Weight | 322.27 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Class | Linear 1,3-diarylpropanoids |
| Subclass | Chalcones and dihydrochalcones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Retrochalcones |
| Alternative Parents | Cinnamic acids and derivatives Benzoxazolones Aryl ketones Benzoyl derivatives Catechols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Alpha-branched alpha,beta-unsaturated ketones Heteroaromatic compounds Enones Acryloyl compounds Oxazoles Oxacyclic compounds Azacyclic compounds Nitriles Hydrocarbon derivatives Organic oxides |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Retrochalcone - Cinnamic acid or derivatives - Benzoxazolone - Benzoxazole - Benzoyl - Catechol - Aryl ketone - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Alpha-branched alpha,beta-unsaturated-ketone - Benzenoid - Heteroaromatic compound - Acryloyl-group - Enone - Oxazole - Azole - Alpha,beta-unsaturated ketone - Ketone - Nitrile - Carbonitrile - Azacycle - Organoheterocyclic compound - Oxacycle - Organonitrogen compound - Cyanide - Organic oxygen compound - Organooxygen compound - Organic nitrogen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. |
| External Descriptors | Not available |
| Solubility | DMSO : 100 mg/mL (310.30 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 322.270 g/mol |
| XLogP3 | 2.100 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 3 |
| Exact Mass | 322.059 Da |
| Monoisotopic Mass | 322.059 Da |
| Topological Polar Surface Area | 120.000 Ų |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Complexity | 607.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 1 |
| Covalently-Bonded Unit Count | 1 |