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Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Coronaridine, an iboga type alkaloid, inhibits the wnt signaling pathway by decreasing β-catenin expression.
In Vitro
Coronaridine (0-40 μM; 24 hours) is against non-cancer cells with IC 50 values >40 μM. It agaisnt wnt-dependent cells with IC 50 values of 10.4, 11.6 and 24.4 μM for SW480, HCT116 and DLD1cells, respectively. Coronaridine (0-40 μM; 24 hours) inhibits β-catenin expression, but the protein levels of p-β--catenin at Ser33, Ser37, and Thr41 and p-β-catenin at Ser 45 [p-b-catenin (S45)] are unchanged. In whole-cell patch clamp recordings,Catharanthine (1-300 μM) are respectively co-applied with GABA at concentrations corresponding to the EC 30 value for each receptor subtype. Both congeners potentiated different GABAARs in a concentration-dependent manner. At higher concentrations, however, Catharanthine starts to inhibit GABA-activated currents due to the reduced amplitude and rebound current, where the threshold concentration depended on the receptor subtype (e.g., > 30 μM for hα1β2; > 100 μM for hα1β2γ2 and hα2β2γ2). The PAM activity of Catharanthine's are depended on the receptor subtype: hα1β2 (4.6±0.8 μM), >hα2β2γ2 (12.6±3.8 μM), hα1β2γ2 (14.4 ± 4.6 μM). MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
| Canonical Smiles | CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC |
|---|---|
| IUPAC Name | methyl (1S,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate |
| InChIKey | NVVDQMVGALBDGE-PZXGUROGSA-N |
| INCHI | 1S/C21H26N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,13-14,19,22H,3,8-12H2,1-2H3/t13-,14+,19+,21-/m1/s1 |
| Isomeric SMILES | CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC |
| Alternate CAS | 467-77-6,4503-12-2 (mono-hydrochloride) |
| PubChem CID | 6426909 |
| MeSH Entry Terms | coronardine;coronardine monohydrochloride;coronardine monohydrochloride, (+-)-isomer;coronaridine |
| Molecular Weight | 338.44 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Alkaloids and derivatives |
| Class | Ibogan-type alkaloids |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Ibogan-type alkaloids |
| Alternative Parents | 3-alkylindoles Pyrroloazepines Piperidinecarboxylic acids Aralkylamines Azepines Benzenoids Methyl esters Heteroaromatic compounds Pyrroles Amino acids and derivatives Trialkylamines Monocarboxylic acids and derivatives Azacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Ibogan skeleton - Catharanthine skeleton - Pyrroloazepine - 3-alkylindole - Indole - Indole or derivatives - Piperidinecarboxylic acid - Azepine - Aralkylamine - Piperidine - Benzenoid - Pyrrole - Methyl ester - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Amino acid or derivatives - Carboxylic acid ester - Organoheterocyclic compound - Carboxylic acid derivative - Azacycle - Monocarboxylic acid or derivatives - Organic oxide - Organic oxygen compound - Amine - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Organic nitrogen compound - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond. |
| External Descriptors | Not available |
| Molecular Weight | 338.400 g/mol |
|---|---|
| XLogP3 | 3.500 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Exact Mass | 338.199 Da |
| Monoisotopic Mass | 338.199 Da |
| Topological Polar Surface Area | 45.300 Ų |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Complexity | 552.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
