(4,5,17-Trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-8-yl) 2-hydroxy-2-methylbutanoate
Basic information
- CAS
1259-86-5- Standard SMILES
CCC(C)(O)C(=O)OC1C(=O)OC2CC3C(C)=CC(=O)C(O)C3(C)C3C4(O)OCC23C1C(C)C4O- InChIKey
WRBGCYVAJRRQKP-UHFFFAOYSA-N- Molecular formula
- C25H34O10
- Average molar mass
- 494.5 g/mol
- Monoisotopic mass
- 494.21519728
Overview
(4,5,17-Trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-8-yl) 2-hydroxy-2-methylbutanoate has been reported in Ailanthus and Simarouba amara with data available.
Names & identifiers
- Preferred name
- (4,5,17-Trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-8-yl) 2-hydroxy-2-methylbutanoate
- IUPAC
- (4,5,17-trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-8-yl) 2-hydroxy-2-methylbutanoate
- English name
- glaucarubinone
- Molecular formula
- C25H34O10
- Molecular weight
- 494.53
Names & synonyms
NSC277286NSC 277286NSC132791Neuro_000064CHEMBL1728992Butyric acid, 4-ester with 1,3a.beta.,4,7,7a.alpha.,11,11a,11b.alpha.-octahydro-1.alpha.,2.alpha.,4.beta.,11.beta.-tetrahydroxy-3.alpha.,8,11a.beta.-trimethyl-2H-1,11c.beta.-(epoxymethano)phenanthro[10,1-bc]pyran-5,10(3H,6a.beta.H)-dionePicras-3-ene-2, 11,20-epoxy-1,11,12-trihydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)-, [1.beta.,11.beta.,12.alpha.,15.beta.(S)]-SMR001566819(trihydroxy-trimethyl-dioxo-[?]yl) 2-hydroxy-2-methyl-butanoateButyric acid, 2-hydroxy-2-methyl-, 4-ester with 1,3a.beta.,4,7,7a.alpha.,11,11a,11b.alpha.-octahydro-1.alpha.,2.alpha.,4.beta., 11.beta.-tetrahydroxy-3.alpha.,8,11a.beta.-trimethyl-2H-1, {11c.beta.-(epoxymethano)phenanthro[10,1-bc]pyran-5,10(3H,} 6a.beta.H)-dioneButyric acid, 2-hydroxy-2-methyl-, 4-ester with 1,3ab,4,7,7aa,11,11a,11ba-octahydro-1a,2a,4b, 11b-tetrahydroxy-3a,8,11ab-trimethyl-2H-1, {11cb-(epoxymethano)phenanthro[10,1-bc]pyran-5,10(3H,6abH)-dione}Picras-3-ene-2,16-dione, 11,20-epoxy-1,11,12-trihydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)-, {[1.beta.,} 11.beta.,12.alpha.,15.beta.(S)]-
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 160 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 4
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 1,020
Physicochemical properties
- Melting point
- 228 · 228-230 °C
- Boiling point
- 714.1 · 714.1±60.0 °C(Predicted)
- Density
- 1.44 · 1.44±0.1 g/cm3(Predicted)
- pka
- 11.63 · 11.63±0.70(Predicted)
- form
- Solid
- color
- White to off-white
Chemistry & industry
Applications
Uses(+)-Glaucarubinone is a potent AP-1 (activator protein-1) inhibitor with an EC50 value of 0.13 μM. (+)-Glaucarubinone shows noncytotoxic[1].
Additional notes
DefinitionChEBI: Glaucarubinone is a quassinoid with formula C25H34O10. It is a natural product isolated from several plant species and exhibits anti-cancer and anti-malarial properties. It has a role as a geroprotector, a plant metabolite, an antineoplastic agent and an antimalarial. It is a carboxylic ester, a quassinoid, an organic heteropentacyclic compound, a tetrol, a secondary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone.
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