lovastatin   Click here for help

GtoPdb Ligand ID: 2739

Synonyms: (+)-mevinolin | 6α-methylcompactin | Mevacor®
Approved drug PDB Ligand Immunopharmacology Ligand
lovastatin is an approved drug (FDA (1987))
Comment: Lovastatin is a 3-hydroxy-3-methylglutaryl-CoA reductase (HMG-CoA) inhibitor; a statin drug used for the prevention of cardiovascular diseases.
NB: there may be ambiguity in the chiral specification in the reported literature, compared to the structure represented here.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 72.83
Molecular weight 404.26
XLogP 4.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCC(C(=O)OC1CC(C)C=C2C1C(CCC1CC(O)CC(=O)O1)C(C=C2)C)C
Isomeric SMILES CC[C@@H](C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
InChI InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
InChI Key PCZOHLXUXFIOCF-BXMDZJJMSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1987))
IUPAC Name Click here for help
[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
International Nonproprietary Names Click here for help
INN number INN
6074 lovastatin
Synonyms Click here for help
(+)-mevinolin | 6α-methylcompactin | Mevacor®
Database Links Click here for help
BindingDB Ligand 34168
CAS Registry No. 75330-75-5 (source: Scifinder)
ChEBI CHEBI:40303
ChEMBL Ligand CHEMBL503
DrugBank Ligand DB00227
DrugCentral Ligand 1612
GtoPdb PubChem SID 135652701
PubChem CID 53232
RCSB PDB Ligand 803
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Wikipedia Lovastatin

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Tocris
Lovastatin
Cat. No. 1530