4,4,6a,9-Tetramethyl-1,2,3,4,4a,5,6,6a,11b,13b-decahydrobenzo[a]furo[2,3,4-mn]xanthen-11-ol
Siccanin · Sicanina · Siccanine · NSC 135048 · Siccaninum · CS 280, SI 23548 · Siccanin USP/EP/BP · Sicanina [inn-spanish]
![Molekülstruktur von 4,4,6a,9-Tetramethyl-1,2,3,4,4a,5,6,6a,11b,13b-decahydrobenzo[a]furo[2,3,4-mn]xanthen-11-ol](/img/chemical/282001.png)
Identifikatoren & physikalische Daten
| CAS No. | 22733-60-4 |
|---|---|
| Summenformel | C22H30O3 |
| Durchschnittliche Molmasse | 342,5 g/mol |
| Monoisotopische Masse | 342,21949481 g/mol |
| SMILES | Cc1cc(O)c2c(c1)OC1(C)CCC3C(C)(C)CCCC34COC2C14 |
| InChIKey | UGGAILYEBCSZIV-UHFFFAOYSA-N |
| PubChem CID | 282001 |
| ChEMBL | CHEMBL1416486 |
Chemische & physikalische Eigenschaften
| XLogP | 4,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,7 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 25 |
| Formalladung | 0 |
| Komplexität | 559 |
| Schmelzpunkt | 139-140° |
| Siedepunkt | 427.8±45.0 °C(Predicted) |
| Dichte | 1.18±0.1 g/cm3(Predicted) |
| Lagerbedingungen | Store at -20°C |
| Löslichkeit | DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble |
| Aggregatzustand | A solid |
| pKa (Säurekonstante) | 10.9(at 25℃) |
Sicherheit & Vorschriften
| Toxizität | LD50 in mice, rats (mg/kg): >6000, >1000 orally>3000, >600 s.c. or i.p. (Suzuki) |
|---|
Anwendungen & Verwendung
Beschreibung
Siccanin is an inhibitor of mitochondrial complex II (succinate dehydrogenase; IC50s = 0.87 and 9.3 μM for P. aeruginosa and rat mitochondria, respectively). It inhibits the growth of T. mentagrophytes (IC50 = 0.3 μg/ml) via inhibition of succinate oxidation in the mitochondria. It also inhibits the growth of C. albicans strains with IC50 values ranging from 5-40 and 80-90 μg/ml for aerobic and anaerobic conditions, respectively.
Verwenden
Siccanin is an unusual, fused, phenolic pentacycle first isolated from Helminthosporium siccans and reported in 1962 as a potent antifungal agent. Siccanin inhibits succinate dehydrogenase in the terminal electron transport system. More recent studies note the proximity of the siccanin binding site to the quinone-binding site of the enzyme. Species-selective inhibition by siccanin is unique among succinate dehydrogenase inhibitors and offers a lead for new chemotherapeutics.