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]
![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 분자 구조식](/img/chemical/282001.png)
식별자 및 물리적 특성
| CAS No. | 22733-60-4 |
|---|---|
| 분자식 | C22H30O3 |
| 평균 분자량 | 342.5 g/mol |
| 단동위원소 질량 | 342.21949481 g/mol |
| SMILES | Cc1cc(O)c2c(c1)OC1(C)CCC3C(C)(C)CCCC34COC2C14 |
| InChIKey | UGGAILYEBCSZIV-UHFFFAOYSA-N |
| PubChem CID | 282001 |
| ChEMBL | CHEMBL1416486 |
화학 및 물리적 성질
| XLogP | 4.9 |
|---|---|
| 극성 표면적 | 38.7 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 25 |
| 형식 전하 | 0 |
| 복잡도 | 559 |
| 녹는점 | 139-140° |
| 끓는 점 | 427.8±45.0 °C(Predicted) |
| 밀도 | 1.18±0.1 g/cm3(Predicted) |
| 저장 조건 | Store at -20°C |
| 용해도 | DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | 10.9(at 25℃) |
안전 및 규제
| 독성 | LD50 in mice, rats (mg/kg): >6000, >1000 orally>3000, >600 s.c. or i.p. (Suzuki) |
|---|---|
| 기존화학 물질 | KE-09390 |
용도
개요
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.
용도
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.