Brusatol
Basic information
- CAS
14907-98-3- Standard SMILES
COC(=O)[C@@]12OC[C@]34[C@H]([C@@H](O)[C@@H]1O)[C@@]1(C)CC(=O)C(O)=C(C)[C@@H]1C[C@H]3OC(=O)[C@H](OC(=O)C=C(C)C)[C@@H]24- InChIKey
ZZZYHIMVKOHVIH-VILODJCFSA-N- Molecular formula
- C26H32O11
- Average molar mass
- 520.5 g/mol
- Monoisotopic mass
- 520.19446183
Overview
Brusatol is a triterpenoid.
Names & identifiers
- Preferred name
- Brusatol
- IUPAC
- methyl (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[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
- English name
- brusatol
- Molecular formula
- C26H32O11
- Molecular weight
- 520.53
Names & synonyms
Brusatol14907-98-3YatansinDTXSID701641633ATY6SZ64BNSC-172924methyl (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[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylatemethyl (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(12.5.0.01,6.02,17.08,13)nonadec-9-ene-17-carboxylateRefChem:121751DTXCID8086654(11 beta,12 alpha,15 beta)-13,20-epoxy-3,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)-2,16-dioxopicras-3-en-21-oic acid, methyl ester(+)-Brusatol
Show more names
Brustaol100935Brusato1Brusatol - Bio-X ?Brusatol >=95% (HPLC)Brusatol (NSC 172924)Brusatol, 10 mM in DMSO
NSC 172924MFCD01746220CHEBI:3197CHEMBL459546MFCD23726642(1R,2S,3S,3aS,3a1R,4R,6aR,7aR,11aS,11bR)-Methyl 1,2,9-trihydroxy-8,11a-dimethyl-4-((3-methylbut-2-enoyl)oxy)-5,10-dioxo-2,3,3a,4,5,6a,7,7a,10,11,11a,11b-dodecahydro-1H-3,3a1-(epoxymethano)dibenzo[de,g]chromene-3-carboxylateBRN 1444847methyl (1R,2S,3S,3aS,3a1R,4R,6aR,7aR,11aS,11bR)-1,2,9-trihydroxy-8,11a-dimethyl-4-((3-methylbut-2-enoyl)oxy)-5,10-dioxo-1,4,5,6a,7,7a,10,11,11a,11b-decahydro-2H-3,3a1-(epoxymethano)dibenzo[de,g]chromene-3(3aH)-carboxylate
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
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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