Methyl 10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
Basic information
- CAS
14907-98-3- Standard SMILES
COC(=O)C12OCC34C(CC5C(C)=C(O)C(=O)CC5(C)C3C(O)C1O)OC(=O)C(OC(=O)C=C(C)C)C24- InChIKey
ZZZYHIMVKOHVIH-UHFFFAOYSA-N- Molecular formula
- C26H32O11
- Average molar mass
- 520.5 g/mol
- Monoisotopic mass
- 520.19446183
Overview
CID 299645 has been reported in Brucea javanica with data available.
Names & identifiers
- Preferred name
- Methyl 10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
- IUPAC
- methyl 10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
- English name
- brusatol
- Molecular formula
- C26H32O11
- Molecular weight
- 520.53
Names & synonyms
MLS002702060NSC172924SMR001565631Brusatol [M+H]+cid_299645CHEMBL1702665BDBM93927s7956methyl 10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylateNCI60_001399methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6.0^{2,17.0^{8,13]nonadec-9-ene-17-carboxylateBrustaol
Show more names
100935Brusato1YatansinNSC 172924(+)-BrusatolBrusatol - Bio-X ?Brusatol >=95% (HPLC)Brusatol (NSC 172924)Brusatol, 10 mM in DMSO
Database identifiers
- CAS
14907-98-3- PubChem CID
- 299645
- ChEMBL
CHEMBL1702665
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 166 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 5
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 1,150
Physicochemical properties
- Boiling point
- 724.3 · 724.3±60.0 °C(Predicted)
- Density
- 1.46 · 1.46±0.1 g/cm3 (20 ºC 760 Torr)
- storage temp.
- -20 °C · -20°C
- solubility
- 1 mg/ml; · DMF: 1 mg/ml; DMSO: 1 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
- pka
- 8.81 · 8.81±0.70(Predicted)
- form
- powder
- color
- white to beige
- optical activity
- 35 to · [α]/D +35 to +44°, c = 0.5 in acetone
- biological source
- (Brucia javanica)
- InChIKey
- ZZZYHIMVKOHVIH-YHSWLYNENA-N
- SMILES
- CC1=C(O)C(C[C@@]2(C)[C@@]1([H])C[C@]3([H])[C@]45[C@]2([H])[C@@H](O)[C@H](O)[C@](OC5)(C(OC)=O)[C@]4([H])[C@@H](OC(C=C(C)C)=O)C(O3)=O)=O
- LogP
- 0.393 · 0.393 (est)
- FDA UNII
- 3 ATY6SZ64B · 3ATY6SZ64B
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
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
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
UsesBrusatol has been used to study the protective role of Nrf2 (nuclear factor, erythroid 2 like 2 ) in intestinal ischemia/reperfusion induced injury.
Additional notes
DefinitionChEBI: Brusatol is a triterpenoid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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