Basic information
- CAS
901309-41-9- Standard SMILES
CC[C@H](C)/C=C(C)/C=C/C1=CC2=CC3=C(C(C)=O)C(=O)O[C@@]3(C)[C@H](O)C2=CO1- InChIKey
QXVIQXFZWZQGMX-CBNFSBMOSA-N- Molecular formula
- C23H26O5
- Average molar mass
- 382.4 g/mol
- Monoisotopic mass
- 382.17802393
Overview
Rotiorinol A is an azaphilone that is 9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one substituted by an acetyl group at position 3, a hydroxy group at position 9, a 3,5-dimethylhepta-1,3-dien-1-yl group at position 6 and a methyl group at position 9a. It has been isolated from Chaetomium cupreum and exhibits antifungal activity. It has a role as an antifungal agent and a Chaetomium metabolite. It is an organic heterotricyclic compound, a gamma-lactone, an azaphilone and a methyl ketone.
Names & identifiers
- Preferred name
- Rotiorinol A
- IUPAC
- (9R,9aR)-3-acetyl-6-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-9-hydroxy-9a-methyl-9H-furo[3,2-g]isochromen-2-one
Names & synonyms
ROTIORINOL ACHEBI:68785(9R,9aR)-3-acetyl-6-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-9-hydroxy-9a-methyl-9H-furo[3,2-g]isochromen-2-one901309-41-9(9R,9aR)-3-acetyl-6-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-9-hydroxy-9a-methyl-9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one6-acetyl-3-(3,5-dimethyl-1E,3E-heptadienyl)-9R-hydroxy-8a(R)-methyl-7H-furo[2,3-g]-2-benzopyran-7-one(9R,9aR)-3-acetyl-6-((1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl)-9-hydroxy-9a-methyl-9,9a-dihydro-2H-furo(3,2-g)isochromen-2-one(9R,9aR)-3-acetyl-6-((1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl)-9-hydroxy-9a-methyl-9H-furo(3,2-g)isochromen-2-one6-Acetyl-3-(3,5-dimethyl-1E,3E-heptadienyl)-9R-hydroxy-8a(R)-methyl-7H-furo(2,3-g)-2-benzopyran-7-oneRefChem:179952CHEMBL525184DTXSID701318031
Show more names
Q27137176(9R,9aR)-3-Acetyl-6-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-9-hydroxy-9a-methyl-9,9a-dihydro-2H-furo[3,2-g][2]benzopyran-2-one
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 72.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 909
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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