tirotundin   Click here for help

GtoPdb Ligand ID: 8700

Comment: Tirotundin is a plant-derived sesquiterpene lactone isolated from Tithonia rotundifolia, which acts a dual activator of PPARα and PPARγ [1]. This is one of the active components found in Chinese traditional medicines used to treat diabetes and hepatitis. Activation of PPARγ is responsible for the compound's anti-diabetic effect. Tirotundin-induced activation of PPARα may improve dyslipidemia.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 82.06
Molecular weight 352.19
XLogP 2.25
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C(C(C)C)OC1CC2(C)CCC(O2)(C(CC2C1C(=C)C(=O)O2)C)O
Isomeric SMILES O=C(C(C)C)O[C@@H]1C[C@]2(C)CC[C@@](O2)([C@H](C[C@@H]2[C@@H]1C(=C)C(=O)O2)C)O
InChI InChI=1S/C19H28O6/c1-10(2)16(20)24-14-9-18(5)6-7-19(22,25-18)11(3)8-13-15(14)12(4)17(21)23-13/h10-11,13-15,22H,4,6-9H2,1-3,5H3/t11-,13+,14+,15-,18-,19+/m0/s1
InChI Key VKWNXJLVNFOOOS-QNIDSSLUSA-N
Classification Click here for help
Compound class Natural product or derivative
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CAS Registry No. 56377-67-4 (source: PubChem)
ChEMBL Ligand CHEMBL464453
GtoPdb PubChem SID 252166900
PubChem CID 9975297
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