o-hydroxyatorvastatin   Click here for help

GtoPdb Ligand ID: 6705

Synonyms: BMS-243887
PDB Ligand
Compound class: Synthetic organic
Comment: One of the active metabolites of the approved drug atorvastatin.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 5
Rotatable bonds 13
Topological polar surface area 132.02
Molecular weight 574.25
XLogP 5.7
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES OC(CC(CC(=O)O)O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1O
Isomeric SMILES O[C@@H](C[C@H](CC(=O)O)O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1O
InChI InChI=1S/C33H35FN2O6/c1-20(2)31-30(33(42)35-26-10-6-7-11-27(26)39)29(21-8-4-3-5-9-21)32(22-12-14-23(34)15-13-22)36(31)17-16-24(37)18-25(38)19-28(40)41/h3-15,20,24-25,37-39H,16-19H2,1-2H3,(H,35,42)(H,40,41)/t24-,25-/m1/s1
InChI Key CZBPKFICAYVHHM-JWQCQUIFSA-N
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
hydroxymethylglutaryl-CoA reductase Rn Inhibitor Inhibition 7.6 pKd - 1
pKd 7.6 (Kd 2.74x10-8 M) [1]