Basic information
- CAS
57629-50-2- Standard SMILES
COC(=O)[C@@]12OC[C@]34[C@H]([C@@H](O)[C@@H]1O)[C@@]1(C)[C@H](O)C(=O)C=C(C)[C@@H]1C[C@H]3OC(=O)[C@H](OC(=O)CC(C)C)[C@@H]24- InChIKey
NTBOLWMPXFGUHO-FTSLJJEMSA-N- Molecular formula
- C26H34O11
- Average molar mass
- 522.5 g/mol
- Monoisotopic mass
- 522.2101119
Overview
Isobrucein A is a quassinoid consisting of a heteropentacyclic skeleton containing a delta-lactone moiety which is substituted at the alpha-carbon by a 3-methylbutanoyloxy group. It has a role as a metabolite and an antineoplastic agent. It is a delta-lactone, a secondary alpha-hydroxy ketone, a methyl ester, a triol, a cyclic ether, an organic heteropentacyclic compound, an enone, an enoate ester and a quassinoid.
Names & identifiers
- Preferred name
- Isobrucein A
- IUPAC
- methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbutanoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
Names & synonyms
ISOBRUCEIN A57629-50-2methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbutanoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylateCHEBI:5987C08769Q27106962methyl (1beta,11beta,12alpha,15beta)-1,11,12-trihydroxy-15-[(3-methylbutanoyl)oxy]-2,16-dioxo-13,20-epoxypicras-3-en-21-oate
Database identifiers
- CAS
57629-50-2- PubChem CID
- 441802
- ChEMBL
CHEMBL558951- ChEBI
CHEBI:5987- Nikkaji
- J40.237K
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 166 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 6
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 1,080
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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