22733-60-4

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22733-60-4 Structure

Identification	Back Directory
[Name] Siccanin
[CAS] 22733-60-4
[Synonyms] Siccanin Sicanina Siccanine Siccaninum NSC 135048 CS 280, SI 23548 Siccanin USP/EP/BP Siccanine [inn-french] Sicanina [inn-spanish] 1,2,3,4,4a,5,6,6a,11b,13b-Decahydro-4,4,6a,9-tetramethyl-13H-benzo[a]furo[2,3,4-mn]xanthen-11-ol 13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol, 1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl- (8CI) (13As)-1,2,3,4,4abeta,5,6,6A,11bbeta,13bbeta-decahydro-4,4,6abeta,9-tetramethyl-13H-benzo(A)furo(2,3,4-mn)xanthen-11-ol 1H,11bH,13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol, 2,3,4,4a,5,6,6a,13b-octahydro-4,4,6a,9-tetramethyl-, (4aS,6aS,11bR,13aS,13bS)- 13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol, 1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl-, (4aS,6aS,11bR,13aS,13bS)- (9CI) 13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol, 1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl-, [4aS-(4aa,6aa,11ba,13aR,13ba)]- 13H-Benzo(A)furo(2,3,4-mn)xanthen-11-ol, 1,2,3,4,4A,5,6,6A,11B,13B-decahydro-4,4,6A,9-tetramethyl-, (4as-(4aalpha,6aalpha,11balpha,13ar,13balpha))-
[Molecular Formula] C22H30O3
[MDL Number] MFCD32269323
[MOL File] 22733-60-4.mol
[Molecular Weight] 342.47

Chemical Properties	Back Directory
[Melting point ] 139-140°
[alpha ] D20 -136° (c = 2 in chloroform)
[Boiling point ] 427.8±45.0 °C(Predicted)
[density ] 1.18±0.1 g/cm3(Predicted)
[storage temp. ] Store at -20°C
[solubility ] DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
[form ] A solid
[pka] 10.9(at 25℃)

Hazard Information	Back Directory
[Description] 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.
[Uses] Siccanin is an antifungal and SDHB (IP) inhibitor.
[Uses] 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.
[Definition] ChEBI: Siccanin is an organic heteropentacyclic compound. It has a role as an antifungal drug and a fungal metabolite.
[storage] Store at -20°C

Safety Data	Back Directory
[Toxicity] LD50 in mice, rats (mg/kg): >6000, >1000 orally; >3000, >600 s.c. or i.p. (Suzuki)

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