mevastatin   Click here for help

GtoPdb Ligand ID: 3031

Synonyms: compactin [2] | ML-236B [6]
PDB Ligand
Compound class: Synthetic organic
Comment: Mevastatin, originally isolated from Penicillium citrinum, was the first HMG-CoA reductase inhibitor (statin) to be identified [6].
Note, the structure presented here is a representative one, as there is some ambiguity in the stereoisomeric specification, see [2] and [5] for the primary references.
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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 390.24
XLogP 4.07
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCC(C(=O)OC1CCC=C2C1C(CCC1CC(O)CC(=O)O1)C(C=C2)C)C
Isomeric SMILES CC[C@@H](C(=O)O[C@H]1CCC=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/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1
InChI Key AJLFOPYRIVGYMJ-INTXDZFKSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
International Nonproprietary Names Click here for help
INN number INN
4943 mevastatin
Synonyms Click here for help
compactin [2] | ML-236B [6]
Database Links Click here for help
CAS Registry No. 73573-88-3
ChEMBL Ligand CHEMBL54440
DrugBank Ligand DB06693
GtoPdb PubChem SID 135650602
PubChem CID 64715
RCSB PDB Ligand 2UO
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Wikipedia Mevastatin

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Tocris
Mevastatin
Cat. No. 1526