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≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Dihydromunduletone (DHM) is a rotenoid derivative and a selective, potent adhesion G protein-coupled receptor (aGPCR) ( GPR56 and GPR114/ADGRG5 ) antagonist with an IC 50 of 20.9 μM for GPR56 , but not inhibit GPR110 or class A GPCRs
In Vitro
Assays are initiated by the addition of [ 35 S]GTPγS, and the rates of aGPCR-stimulated G protein activation ([ 35 S]GTPγS binding to Gα) are measured with or without the influence of added compounds. Dihydromunduletone (DHM) inhibits the kinetics of GPR56 7TM-stimulated G13 GTPγS binding to varying degrees. Dihydromunduletone is the best inhibitory compound and reduced the rate at which GPR56 7TM activated G13 >75% (from 0.18 to 0.04 minute −1 ). At a concentration of Dihydromunduletone (DHM) that maximally inhibits GPR56 (50 μM), the rate of GPR114 7TM-stimulated Gs activity is also inhibited dramatically. When Dihydromunduletone (50 μM) is applied to the GPR110 7TM, it fails to inhibit GPR110 stimulation of Gq GTPγS binding. Cells transfected with GPR56 A386M 7TM are incubated with increasing concentrations of Dihydromunduletone. P7 peptide agonist is added, and SRE-luciferase activity is measured. Dihydromunduletone inhibits the P7 peptide-induced luciferase activity in a concentration-dependent manner. Cells are also treated with a fixed concentration of 3 µM Dihydromunduletone and then stimulated with an increasing concentration of P7 peptide agonist. Dihydromunduletone treatment blunts P7 peptide activation at each concentration. In conclusion, Dihydromunduletone antagonizes synthetic-peptide agonist and tethered-peptide agonist-mediated aGPCR activation in isolated membranes and HEK293T cell-based assays, but it does not inhibit basal receptor signaling. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:IC50: 20.9 μM (GPR56), ,GPR114
| Sonrisas canónicas | CC1(C=CC2=C(O1)C=CC(=C2OC)CC(=O)C3=C(C=C4C(=C3)CC(C(O4)(C)C)O)O)C |
|---|---|
| IUPAC Name | 1-(3,7-dihydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-2-(5-methoxy-2,2-dimethylchromen-6-yl)ethanone |
| InChIKey | RMVZECFNOTWEKD-UHFFFAOYSA-N |
| INCHI | 1S/C25H28O6/c1-24(2)9-8-16-20(30-24)7-6-14(23(16)29-5)11-18(26)17-10-15-12-22(28)25(3,4)31-21(15)13-19(17)27/h6-10,13,22,27-28H,11-12H2,1-5H3 |
| Isómeros SMILES | CC1(C=CC2=C(O1)C=CC(=C2OC)CC(=O)C3=C(C=C4C(=C3)CC(C(O4)(C)C)O)O)C |
| CAS alternativo | 674786-20-0 |
| PubChem CID | 3492326 |
| Términos de entrada MeSH | dihydromunduletone |
| Peso molecular | 424.49 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Clase | Stilbenes |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Stilbenes |
| Alternative Parents | 2,2-dimethyl-1-benzopyrans Aryl alkyl ketones Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Secondary alcohols Oxacyclic compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Stilbene - 2,2-dimethyl-1-benzopyran - Chromane - Benzopyran - 1-benzopyran - Aryl alkyl ketone - Aryl ketone - Anisole - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Vinylogous acid - Ketone - Secondary alcohol - Ether - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Organic oxide - Alcohol - Hydrocarbon derivative - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. |
| External Descriptors | Not available |
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| Solubilidad | DMSO : 250 mg/mL (588.94 mM; Need ultrasonic) |
|---|---|
| Peso molecular | 424.500 g/mol |
| XLogP3 | 4.300 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 4 |
| Exact Mass | 424.189 Da |
| Monoisotopic Mass | 424.189 Da |
| Topological Polar Surface Area | 85.200 Ų |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Complexity | 700.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |