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
References
1. Sarver RW, Bills E, Bolton G, Bratton LD, Caspers NL, Dunbar JB, Harris MS, Hutchings RH, Kennedy RM, Larsen SD et al.. (2008)
Thermodynamic and structure guided design of statin based inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase.
J Med Chem, 51 (13): 3804-13. [PMID:18540668]