8,12,16,16-Tetramethyl-3,11-dioxapentacyclo[10.7.1.01,15.04,20.05,10]icosa-5,7,9-trien-6-ol
Basic information
- CAS
22733-60-4- Standard SMILES
Cc1cc(O)c2c(c1)O[C@@]1(C)CC[C@H]3C(C)(C)CCCC34CO[C@@H]2[C@H]41- InChIKey
UGGAILYEBCSZIV-NPVRBOKNSA-N- Molecular formula
- C22H30O3
- Average molar mass
- 342.5 g/mol
- Monoisotopic mass
- 342.21949481
Overview
See also: Siccanin (annotation moved to).
Names & identifiers
- Preferred name
- 8,12,16,16-Tetramethyl-3,11-dioxapentacyclo[10.7.1.01,15.04,20.05,10]icosa-5,7,9-trien-6-ol
- IUPAC
- (4R,12S,15S,20S)-8,12,16,16-tetramethyl-3,11-dioxapentacyclo[10.7.1.01,15.04,20.05,10]icosa-5,7,9-trien-6-ol
- English name
- Siccanin
- Molecular formula
- C22H30O3
- Molecular weight
- 342.47
Names & synonyms
22733-60-4NCGC00181099-01SCHEMBL153911CHEMBL2358628Tox21_1127158,12,16,16-Tetramethyl-3,11-dioxapentacyclo[10.7.1.01,15.04,20.05,10]icosa-5,7,9-trien-6-olCAS-22733-60-4(4aS,6aS,11bR,13bS)-4,4,6a,9-Tetramethyl-1,2,3,4,4a,5,6,6a,11b,13b-decahydro-13H-benzo[a]furo[2,3,4-mn]xanthen-11-olSiccaninSicaninaSiccanineNSC 135048
Show more names
SiccaninumCS 280, SI 23548Siccanin USP/EP/BPSicanina [inn-spanish]Siccanine [inn-french]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
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 38.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 559
Physicochemical properties
- Melting point
- 139 · 139-140°
- alpha
- 20 · D20 -136° (c = 2 in chloroform)
- Boiling point
- 427.8 · 427.8±45.0 °C(Predicted)
- Density
- 1.18 · 1.18±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
- form
- A solid
- pka
- 10.9 · 10.9(at 25℃)
- FDA UNII
- 702 S858Z6 · L702S858Z6
- Toxicity
- 50 in · LD50 in mice, rats (mg/kg): >6000, >1000 orally; >3000, >600 s.c. or i.p. (Suzuki)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 in mice, rats (mg/kg): >6000, >1000 orally; >3000, >600 s.c. or i.p. (Suzuki)
Chemistry & industry
Applications
DescriptionSiccanin 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.
UsesSiccanin 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.
UsesSiccanin is an antifungal and SDHB (IP) inhibitor.
Additional notes
DefinitionChEBI: Siccanin is an organic heteropentacyclic compound. It has a role as an antifungal drug and a fungal metabolite.
Related reactions
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Compound notes
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