celastrol   

GtoPdb Ligand ID: 10386

Comment: Celastrol is a plant-derived (from Tripterygium wilfordi, the Thunder god vine) natural product that has antioxidant, anti-inflammatory [1,6] and anti-obesity effects [3].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 74.6
Molecular weight 450.28
XLogP 7.98
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C1C=C2C(=CC=C3C2(C)CCC2(C3(C)CCC3(C2CC(C)(CC3)C(=O)O)C)C)C(=C1O)C
Isomeric SMILES O=C1C=C2C(=CC=C3[C@@]2(C)CC[C@@]2([C@]3(C)CC[C@@]3([C@H]2C[C@@](C)(CC3)C(=O)O)C)C)C(=C1O)C
InChI InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
InChI Key KQJSQWZMSAGSHN-JJWQIEBTSA-N
Classification
Compound class Natural product or derivative
IUPAC Name
(2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid
Database Links
BindingDB Ligand 205457
GtoPdb PubChem SID 384403665
PubChem CID 122724
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Tocris
Celastrol
Cat. No. 3203