ragaglitazar   Click here for help

GtoPdb Ligand ID: 2664

PDB Ligand
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 68.23
Molecular weight 419.17
XLogP 4.88
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCOC(C(=O)O)Cc1ccc(cc1)OCCN1c2ccccc2Oc2c1cccc2
Isomeric SMILES CCO[C@H](C(=O)O)Cc1ccc(cc1)OCCN1c2ccccc2Oc2c1cccc2
InChI InChI=1S/C25H25NO5/c1-2-29-24(25(27)28)17-18-11-13-19(14-12-18)30-16-15-26-20-7-3-5-9-22(20)31-23-10-6-4-8-21(23)26/h3-14,24H,2,15-17H2,1H3,(H,27,28)/t24-/m0/s1
InChI Key WMUIIGVAWPWQAW-DEOSSOPVSA-N
References
1. Chakrabarti R, Vikramadithyan RK, Misra P, Hiriyan J, Raichur S, Damarla RK, Gershome C, Suresh J, Rajagopalan R. (2003)
Ragaglitazar: a novel PPAR alpha PPAR gamma agonist with potent lipid-lowering and insulin-sensitizing efficacy in animal models.
Br J Pharmacol, 140 (3): 527-37. [PMID:12970088]
2. Ebdrup S, Pettersson I, Rasmussen HB, Deussen HJ, Frost Jensen A, Mortensen SB, Fleckner J, Pridal L, Nygaard L, Sauerberg P. (2003)
Synthesis and biological and structural characterization of the dual-acting peroxisome proliferator-activated receptor alpha/gamma agonist ragaglitazar.
J Med Chem, 46 (8): 1306-17. [PMID:12672231]
3. Pickavance LC, Brand CL, Wassermann K, Wilding JP. (2005)
The dual PPARalpha/gamma agonist, ragaglitazar, improves insulin sensitivity and metabolic profile equally with pioglitazone in diabetic and dietary obese ZDF rats.
Br J Pharmacol, 144 (3): 308-16. [PMID:15655531]