Ilicicolin F
Basic information
- CAS
22738-98-3- Standard SMILES
CC(=O)O[C@H]1CC(=O)[C@H](C)[C@@](C)(/C=C/C(C)=C/Cc2c(O)c(Cl)c(C)c(C=O)c2O)[C@@H]1C- InChIKey
ACSLMZYXJATICN-IRMIYARYSA-N- Molecular formula
- C25H31ClO6
- Average molar mass
- 463 g/mol
- Monoisotopic mass
- 462.1809164
Overview
Ilicicolin F has been reported in Neonectria ditissima with data available.
Names & identifiers
- Preferred name
- Ilicicolin F
- IUPAC
- [(1S,2S,3S,4R)-3-[(1E,3E)-5-(3-chloro-5-formyl-2,6-dihydroxy-4-methylphenyl)-3-methylpenta-1,3-dienyl]-2,3,4-trimethyl-5-oxocyclohexyl] acetate
- English name
- ILICICOLIN F
- Molecular formula
- C25H31ClO6
- Molecular weight
- 462.96
Names & synonyms
Ilicicolin F22738-98-3B1C42K12CTLL-Z1272.ZETA.LL-Z 1272.ZETA.[(1S,2S,3S,4R)-3-[(1E,3E)-5-(3-chloro-5-formyl-2,6-dihydroxy-4-methylphenyl)-3-methylpenta-1,3-dienyl]-2,3,4-trimethyl-5-oxocyclohexyl] acetate3-((2E,4E)-5-((1S,2S,3S,6R)-3-(Acetyloxy)-1,2,6-trimethyl-5-oxocyclohexyl)-3-methyl-2,4-pentadien-1-yl)-5-chloro-2,4-dihydroxy-6-methylbenzaldehydeBenzaldehyde, 3-((2E,4E)-5-((1S,2S,3S,6R)-3-(acetyloxy)-1,2,6-trimethyl-5-oxocyclohexyl)-3-methyl-2,4-pentadien-1-yl)-5-chloro-2,4-dihydroxy-6-methyl-BENZALDEHYDE, 3-(5-(3-(ACETYLOXY)-1,2,6-TRIMETHYL-5-OXOCYCLOHEXYL)-3-METHYL-2,4-PENTADIENYL)-5-CHLORO-2,4-DIHYDROXY-6-METHYL-, (1S-(1.ALPHA.(2E,4E),2.BETA.,3.ALPHA.,6.BETA.))-LL-Z1272zetaLL-Z 1272zetaUNII-B1C42K12CT
Show more names
Acetoxy-ascochlorin8'-AcetoxyascochlorinIlicicolin F >=98% (HPLC), from Verticillium hemipterigenum5-Chloro-2,4-dihydroxy-6-methyl-3-[(2E,4E)-5-[(1S)-3β-acetoxy-1,2α,6α-trimethyl-5-oxocyclohexyl]-3-methyl-2,4-pentadienyl]benzaldehyde
Properties
Computed structural properties
- XLogP
- 5.8
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 776
Physicochemical properties
- Boiling point
- 597.6 · 597.6±50.0 °C(Predicted)
- Density
- 1.24 · 1.24±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 10 mg/mL · DMSO: ≥10mg/mL
- form
- solid
- pka
- 6.26 · 6.26±0.50(Predicted)
- FDA UNII
- 1 C42K12CT · B1C42K12CT
- WGK Germany
- 3 · 3
- HS Code
- 2941900000 · 2941900000
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
- wgk
- 3
- hs_code
- 2941900000
Chemistry & industry
Applications
UsesIlicicolin F is a fungal metabolite that has been found in Fusarium and has diverse biological activities. It inhibits T. vivax alternative oxidase and the E. coli ubiquinol oxidase cytochrome bo (IC50s=0.43 and 0.37 μM, respectively) but not the E. coli ubiquinol oxidase cytochrome bd (IC50=85 μM).2 Ilicicolin F is active against the fungi A. fumigatus and C. albicans (MICs=1.66-3.33 and 6.66-13.33 μg/mL, respectively). It is cytotoxic to HeLa cells with an EC50 value of 0.003 μg/mL.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…