Compound: Mevastatin
SMILES: O=C1O[C@@H](C[C@H](C1)O)CC[C@@H]2[C@@H]3C(C=C[C@@H]2C)=CCC[C@@H]3OC(=O)[C@H](CC)C
InChIKey: AJLFOPYRIVGYMJ-INTXDZFKSA-N
Synonyms: Mevastatin, compactin, 73573-88-3, Mevastatina, Mevastatine, Mevastatinum, Antibiotic ML 236B, ML-236B lactone, ML-236B, ML236B lactone, ML 236 B, CS 500, CS-500, 1UQM1K0W9X, DTXSID4040684, CS500, NSC-281245, NSC-759322, L-637312, [(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, DTXCID2020684, CHEBI:34848, L637312, NSC281245, 7-(1,2,6,7,8,8a-Hexahydro-2-methyl-8-(2-methylbutyryloxy)naphthyl)-3-hydroxyheptan-5-olide, (1S,7S,8S,8aR)-8-(2-((2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl(2S)-2-methylbutanoate, ML236B, 6-demethylmevinolin, ((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, RefChem:53384, EC 700-442-0, 658-033-7, 700-442-0, Mevastatin [INN], Mevastatinum [INN-Latin], Compactin;ML236B, (1S,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate, MFCD05662341, Mevastatin (Compactin), CHEMBL54440, Butanoic acid, 2-methyl-, (1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, (2S)-, (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, M02108, (1S,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-7-methyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthyl (S)-2-methylbutyrate, Compactin (penicillium), Mevastatine [INN-French], Mevastatina [INN-Spanish], SMR000336944, (+)-Compactin, CCRIS 4505, Lovastatin EP Impurity A, UNII-1UQM1K0W9X, kompaktin, NCGC00095942-01, Mevastatin/Compactin, Mevastatin (Standard), MEVASTATIN [MI], MEVASTATIN [JAN], MEVASTATIN [MART.], SCHEMBL1116, MEVASTATIN [USP-RS], Lopac0_000754, MLS000721804, MLS000759452, MLS001424284, MLS002207227, Compactin, 6-Demethylvevinolin, CS-500, ML-236 B, GTPL3031, Mevastatin - Bio-X trade mark, orb1310389, orb3139879, Mevastatin, >=96% (HPLC), HMS2052P07, HMS2089D10, HMS2232N09, HMS3262G10, HMS3268A19, HMS3412H15, HMS3676H15, HMS3713B06, [(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-tetrahydropyran-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate, MSK10322, Compactin, Mevastatinum, Mevastatina, Tox21_111540, Tox21_500754, BDBM50011036, HY-17408R, NSC779705, s4223, AKOS015994712, Mevastatin, >=95% (HPLC), powder, CCG-101174, CS-1234, DB06693, EBC-615461, FM25991, KS-1085, LP00754, NC00424, NSC 759322, NSC-779705, SDCCGSBI-0050732.P002, SMP1_000077, NCGC00025202-04, NCGC00261439-01, BM164666, Butanoic acid, 2-methyl-, (1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (2S)-, Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1-alpha(R*),7-beta,8-beta(2S*,4S*),8a-beta))-, HY-17408, Mevastatin 100 microg/mL in Acetonitrile, SY077144, CAS-73573-88-3, LOVASTATIN IMPURITY A [EP IMPURITY], EU-0100754, M2275, H11997, M 2537, AB00588266-06, AB00588266-08, AB00588266_09, Q414407, SR-01000729493, SR-01000729493-4, BRD-K94441233-001-03-1, BRD-K94441233-001-12-2, BRD-K94441233-001-13-0, BRD-K94441233-001-17-1, (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate, (S)-((1S,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate, (S)-((1S,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate, (S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester, 2-Methyl-butyric acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester, 2-Methyl-butyric acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester((+)-compactin), 2-Methyl-butyric acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester(compactin), Lovastatin EP Impurity A; Pravastatin Deshydroxy Impurity; Mevastatin; Compactin (Penicillium)
Theoretical properties:
molecular_formula: C23H34O5
molecular_weight: 390.5 g/mol
exact_mass: 390.24062418 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 7
heavy_atom_count: 28
topological_polar_surface_area: 72.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Mevastatin is a carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals. It has a role as an antifungal agent, an apoptosis inducer, a fungal metabolite, a Penicillium metabolite and an EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor. It is a member of hexahydronaphthalenes, a polyketide, a carboxylic ester, a member of 2-pyranones and a statin (naturally occurring).", "chebi": "A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from <em>Penicillium citrinum</em> and from <em>Penicillium brevicompactum</em>, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.", "chembl": "MEVASTATIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Mevastatin (compactin, ML-236B) is a hypolipidemic agent that belongs to the statins class.\nIt was isolated from the mold Penicillium citrinum by Akira Endo in the 1970s, and he identified it as a HMG-CoA reductase inhibitor, i.e., a statin. Mevastatin might be considered the first statin drug; clinical trials on mevastatin were performed in the late 1970s in Japan, but it was never marketed. The first statin drug available to the general public was lovastatin.\nMevastatin has since been derivatized to the compound pravastatin, which is a pharmaceutical used in the lowering of cholesterol and preventing cardiovascular disease.\nIn vitro, it has antiproliferative properties.\nA British group isolated the same compound from Penicillium brevicompactum, named it compactin, and published their results in 1976. The British group mentions antifungal properties with no mention of HMG-CoA reductase inhibition.\nHigh doses inhibit growth and proliferation of melanoma cells."}