1,11,12-Trihydroxy-11,20-epoxypicras-3-ene-2,16-dione
Basic information
- CAS
22611-34-3- Standard SMILES
CC1=CC(=O)C(O)C2(C)C1CC1OC(=O)CC3C(C)C(O)C4(O)OCC13C42- InChIKey
VLYMLZRDCSQUQF-UHFFFAOYSA-N- Molecular formula
- C20H26O7
- Average molar mass
- 378.4 g/mol
- Monoisotopic mass
- 378.16785316
Names & identifiers
- Preferred name
- 1,11,12-Trihydroxy-11,20-epoxypicras-3-ene-2,16-dione
- IUPAC
- 4,5,17-trihydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-ene-9,16-dione
- English name
- chaparrinone
- Molecular formula
- C20H26O7
- Molecular weight
- 378.42
Names & synonyms
DTXSID80945268NSC-2887541,11,12-Trihydroxy-11,20-epoxypicras-3-ene-2,16-dionePicras-3-ene-2, 11,20-epoxy-1,11,12-trihydroxy-, (1.beta.,11.beta.,12.alpha.)-chaparrinonePicras-3-ene-2,16-dione, 11,20-epoxy-1,11,12-trihydroxy-, (1β,11β,12α)-
Database identifiers
- CAS
22611-34-3- PubChem CID
- 324240
- DTXSID
DTXSID80945268
Properties
Computed structural properties
- XLogP
- -0.4
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 0
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 776
Physicochemical properties
- Melting point
- 238 · 238-242 °C
- Boiling point
- 626.1 · 626.1±55.0 °C(Predicted)
- Density
- 1.45 · 1.45±0.1 g/cm3(Predicted)
- pka
- 12.03 · 12.03±0.70(Predicted)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
UsesChaparrinone is a quassinoid that can be isolated from the root of Eurycoma harmandiana. Chaparrinone has antimalarial and cytotoxic activities against Plasmodium falciparum and P-388 cells (IC50: 0.037 and 0.34 μg/mL respectively)[1][2].
Additional notes
DefinitionChEBI: Chaparrinone is a triterpenoid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…