Mevastatin

Details

• Internal ID: 96407907-ca68-4438-8255-c9bfc7972727
• Taxonomy: Organoheterocyclic compounds > Lactones > Delta valerolactones
• IUPAC Name: [(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
• 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
• Popularity: 668 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄O₅
• Molecular Weight: 390.50 g/mol
• Exact Mass: 390.24062418 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.95
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• Compactin
• EC 700-442-0
• Mevastatin
• ML-236B
• Mevastatinum
• Mevastatina
• Mevastatine
• Antibiotic ML 236B
• Mevastatin [INN]
• Mevastatinum [INN-Latin]
• Compactin (penicillium)
• CS 500
• ML 236 B
• CCRIS 4505
• Mevastatine [INN-French]
• UNII-1UQM1K0W9X
• Mevastatina [INN-Spanish]
• 1UQM1K0W9X
• Compactin;ML236B
• DTXSID4040684
• CHEBI:34848
• NSC-759322
• CHEMBL54440
• DTXCID2020684
• ML236B
• NSC 759322
• (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
• (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
• [(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
• Mevastatine (INN-French)
• Mevastatinum (INN-Latin)
• Mevastatina (INN-Spanish)
• MEVASTATIN (MART.)
• MEVASTATIN [MART.]
• 7-(1,2,6,7,8,8a-Hexahydro-2-methyl-8-(2-methylbutyryloxy)naphthyl)-3-hydroxyheptan-5-olide
• MEVASTATIN (USP-RS)
• MEVASTATIN [USP-RS]
• 6-demethylmevinolin
• (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
• 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))-
• Mevastatin (Compactin)
• MFCD05662341
• (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
• 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)-
• SMR000336944
• LOVASTATIN IMPURITY A (EP IMPURITY)
• LOVASTATIN IMPURITY A [EP IMPURITY]
• kompaktin
• NCGC00095942-01
• (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
• (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
• Mevastatin- Bio-X
• MEVASTATIN [MI]
• MEVASTATIN [JAN]
• SCHEMBL1116
• Lopac0_000754
• MLS000721804
• MLS000759452
• MLS001424284
• MLS002207227
• GTPL3031
• Mevastatin, >=96% (HPLC)
• AJLFOPYRIVGYMJ-INTXDZFKSA-N
• HMS2052P07
• HMS2089D10
• HMS2232N09
• HMS3262G10
• HMS3268A19
• HMS3412H15
• HMS3676H15
• HMS3713B06
• Compactin, Mevastatinum, Mevastatina
• Tox21_111540
• Tox21_500754
• BDBM50011036
• CS-500
• NSC779705
• s4223
• AKOS015994712
• Mevastatin, >=95% (HPLC), powder
• CCG-101174
• CS-1234
• DB06693
• KS-1085
• LP00754
• NC00424
• NSC-779705
• SDCCGSBI-0050732.P002
• SMP1_000077
• NCGC00025202-04
• NCGC00261439-01
• BM164666
• HY-17408
• Mevastatin 100 microg/mL in Acetonitrile
• CAS-73573-88-3
• EU-0100754
• M2275
• H11997
• M 2537
• AB00588266-06
• AB00588266-08
• AB00588266_09
• A837861
• Q414407
• SR-01000729493
• L-637312
• SR-01000729493-4
• BRD-K94441233-001-03-1
• BRD-K94441233-001-17-1
• (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
• (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)-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)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9806	98.06%
Caco-2	+	0.6522	65.22%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6141	61.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8092	80.92%
OATP1B3 inhibitior	+	0.9618	96.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8195	81.95%
P-glycoprotein inhibitior	+	0.7995	79.95%
P-glycoprotein substrate	-	0.6189	61.89%
CYP3A4 substrate	+	0.5584	55.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8852	88.52%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	-	0.9291	92.91%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.8901	89.01%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7315	73.15%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9541	95.41%
Skin irritation	+	0.5493	54.93%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8211	82.11%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.8176	81.76%
skin sensitisation	-	0.8532	85.32%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8709	87.09%
Acute Oral Toxicity (c)	III	0.6226	62.26%
Estrogen receptor binding	+	0.9164	91.64%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	-	0.5884	58.84%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	-	0.7059	70.59%
Honey bee toxicity	-	0.8340	83.40%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9907	99.07%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL402	P04035	HMG-CoA reductase	23 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.63%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.88%	97.25%
CHEMBL2581	P07339	Cathepsin D	96.58%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.05%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.60%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.02%	93.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.95%	96.47%
CHEMBL2996	Q05655	Protein kinase C delta	88.90%	97.79%
CHEMBL221	P23219	Cyclooxygenase-1	87.22%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.28%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.86%	90.71%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	84.26%	83.10%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.24%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.69%	99.17%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.62%	96.37%
CHEMBL340	P08684	Cytochrome P450 3A4	81.11%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.05%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.83%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.69%	100.00%
CHEMBL299	P17252	Protein kinase C alpha	80.14%	98.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.00%	86.33%

Plants that contains it

• Genista compacta
• Morus alba

Cross-Links

• PubChem: 64715
• LOTUS: LTS0122611
• wikiData: Q414407