tolrestat   Click here for help

GtoPdb Ligand ID: 7404

Synonyms: Alredase® | AY-27,773 | AY-27773
Approved drug PDB Ligand
tolrestat is an approved drug
Compound class: Synthetic organic
Comment: Tolrestat is an aldose reductase inhibitor [1] that failed Phase 3 clinical trial in the US and never made it to the clinic. The manufacturer withdrew the drug from other markets due to toxicity concerns.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 81.86
Molecular weight 357.06
XLogP 3.99
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc2c(c1C(F)(F)F)cccc2C(=S)N(CC(=O)O)C
Isomeric SMILES COc1ccc2c(c1C(F)(F)F)cccc2C(=S)N(CC(=O)O)C
InChI InChI=1S/C16H14F3NO3S/c1-20(8-13(21)22)15(24)11-5-3-4-10-9(11)6-7-12(23-2)14(10)16(17,18)19/h3-7H,8H2,1-2H3,(H,21,22)
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Molecular structure representations generated using Open Babel