Lovastatin

Details

• Internal ID: 44c6b991-6a51-4748-84fa-135722591f9d
• Taxonomy: Organoheterocyclic compounds > Lactones > Delta valerolactones
• IUPAC Name: [(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
• SMILES (Canonical): CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C
• SMILES (Isomeric): CC[C@H](C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O)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
• Popularity: 6,744 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₆O₅
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.25627424 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.20
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 75330-75-5
• mevinolin
• Mevacor
• Altoprev
• Mevlor
• Sivlor
• Altocor
• MK-803
• Monacolin K
• Lovastatine
• 6alpha-Methylcompactin
• Lovastatina
• Mevinacor
• Lovastatinum [Latin]
• 6-alpha-Methylcompactin
• Lovastatinum
• MK 803
• DTXSID5020784
• 9LHU78OQFD
• NSC-758662
• (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
• L-154803
• C10AA02
• 2beta,6alpha-Dimethyl-8alpha-(2-methyl-1-oxobutoxy)-mevinic acid lactone
• [(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
• DTXCID50784
• (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyrate
• CHEBI:40303
• 6-Methylcompactin
• NSC633781
• Lovastatinum (Latin)
• (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-2-Methylbutanoic acid 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester
• (S)-2-Methylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one
• 1,2,6,7,8,8a-Hexahydro-beta,delta-dihydroxy-2,6-dimethyl-8-(2-methyl-1-oxobutyoxy)-1-naphthaleneheptanoic acid delta-lactone
• Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-
• 1 alpha-Isomer Lovastatin
• 6 Methylcompactin
• (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
• MK803
• alpha-Isomer Lovastatin, 1
• ML-530B
• Mevinacor 10
• Mevinacor 40
• ((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
• (S)-2-Methylbutyric acid, 8-ester with (4R,6R)-6-[2-[(1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl]ethyl]tetrahydro-4-hydroxy-2H-pyran-2-one
• Lovastatin, 1 alpha
• RefChem:5964
• (2S)-2-Methylbutanoic Acid, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl Ester
• (8-(2-(4-hydroxy-6-oxooxan-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate
• 616-212-7
• ((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) (2R)-2-methylbutanoate
• Lovalord
• Nergadan
• Artein
• Lovastatine [French]
• Lovastatina [Spanish]
• Lovalip
• Hipovastin
• Lovasterol
• Cholestra
• Closterol
• Colevix
• Hipolip
• Lestatin
• Lipivas
• Lipofren
• Lovastin
• Lozutin
• Paschol
• Rodatin
• Rovacor
• Tecnolip
• Teroltrat
• Belvas
• Lipdip
• Taucor
• butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, (2S)-
• MFCD00072164
• Lovastatin [USAN]
• MLS000069585
• Lovastatin (Standard)
• 6.alpha.-Methylcompactin
• MSD 803
• SMR000058779
• (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
• C24H36O5
• Lovastatin (Mevacor)
• (S)-(1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoate
• HSDB 6534
• NCGC00023509-03
• Liposcler
• 6 alpha-Methylcompactin
• Rextat
• Monakolin K
• (+)-mevinolin
• (1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate
• [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-tetrahydropyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
• Mevacor (TN)
• CHEMBL503
• Lovastatin & Primycin
• Lovastatin (USP/INN)
• SR-05000001880
• UNII-9LHU78OQFD
• Simvastatin EP Impurity E
• BRN 3631989
• Tancor
• Mevinolin from Aspergillus sp.
• CCRIS 8092
• Mevinacor;
• Lipofren;
• Nergadan;
• Mevacor;
• Lovastatin CRS
• Monacolin K;
• 1cqp
• Lovastatin [USAN:USP:INN:BAN]
• (2S)-2-METHYLBUTANOIC ACID (1S,3R,7S,8S,8AR)-1,2,3,7,8,8A-HEXAHYDRO-3,7-DIMETHYL-8-(2-((2R,4R)-TETRAHYDRO-4-HYDROXY-6-OXO-2H-PYRAN-2-YL)ETHYL)-1-NAPHTHALENYL ESTER
• (2S)-2-Methylbutanoic acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester
• Butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (2S)-
• Prestwick_819
• CAS-75330-75-5
• Mevinolin (lovastatin)
• LOVASTATIN [MI]
• LOVASTATIN [INN]
• Opera_ID_1578
• Prestwick0_000516
• Prestwick1_000516
• Prestwick2_000516
• Prestwick3_000516
• Spectrum3_001873
• Spectrum5_001294
• Lovastatin (MK-803)
• LOVASTATIN [HSDB]
• LOVASTATIN [VANDF]
• EC 616-212-7
• LOVASTATIN [MART.]
• SCHEMBL3136
• LOVASTATIN [USP-RS]
• LOVASTATIN [WHO-DD]
• US9115116, lovastatin
• BIDD:PXR0113
• BSPBio_000471
• BSPBio_001265
• BSPBio_003346
• 74133-25-8
• cid_53232
• MLS001055358
• MLS006011867
• US9353061, Lovastatina
• BIDD:GT0749
• DivK1c_001032
• SPECTRUM1503977
• SPBio_002392
• BPBio1_000519
• GTPL2739
• Lovastatin - Bio-X trade mark
• MEGxm0_000398
• orb1309414
• LOVASTATIN [ORANGE BOOK]
• ACon0_000534
• ACon1_000390
• BDBM34168
• HMS503O05
• HY-N0504R
• KBio1_001032
• KBio3_002848
• LOVASTATIN [EP MONOGRAPH]
• Simvastatin impurity, lovastatin-
• Lovastatin for peak identification
• NINDS_001032
• GLXC-06458
• HMS1569H13
• HMS1792O07
• HMS1923O13
• HMS1990O07
• HMS2089M06
• HMS2093O03
• HMS2096H13
• HMS2236F07
• HMS3039N16
• HMS3259F10
• HMS3268C03
• HMS3403O07
• HMS3412H19
• HMS3676H19
• HMS3713H13
• HMS3884B03
• LOVASTATIN [USP MONOGRAPH]
• Pharmakon1600-01503977
• ADVICOR COMPONENT LOVASTATIN
• ALBB-027272
• BB_NC-01457
• HY-N0504
• MK-803; LOVALIP; MEVACOR
• MSK10235
• Tox21_110888
• Tox21_201475
• Tox21_300268
• BBL024473
• CCG-39627
• EBC-02080
• NSC758662
• NSC779704
• s2061
• SBB080686
• STK801953
• AKOS005267139
• Lovastatin for peak identification CRS
• Lovastatin; Simvastatin EP Impurity E
• Tox21_110888_1
• CS-1990
• DB00227
• FH24950
• KS-1082
• Mevinolin from Aspergillus sp., powder
• NC00713
• NSC 758662
• NSC-633781
• NSC-779704
• IDI1_001032
• NCGC00023509-04
• NCGC00023509-05
• NCGC00023509-06
• NCGC00023509-07
• NCGC00023509-08
• NCGC00023509-09
• NCGC00023509-10
• NCGC00023509-11
• NCGC00023509-13
• NCGC00023509-14
• NCGC00023509-16
• NCGC00254157-01
• NCGC00259026-01
• AC-13961
• BL164644
• Butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (2S)-
• G226
• SMR000673570
• SBI-0051881.P002
• CS-0694830
• L0214
• NS00000544
• SIMVASTATIN IMPURITY E [EP IMPURITY]
• EN300-52515
• C07074
• D00359
• M02056
• AB00052400-17
• AB00052400_18
• AB00052400_19
• Mevinolin from Aspergillus sp., >=98% (HPLC)
• 330L755
• A838030
• Q417740
• SR-01000000123
• SR-01000000123-3
• SR-05000001880-1
• SR-05000001880-2
• BRD-K09416995-001-06-8
• BRD-K09416995-001-21-7
• BRD-K09416995-001-38-1
• BRD-K09416995-001-39-9
• BRD-K09416995-001-40-7
• Mevacor;Monacolin K;mevinolin;6-alpha-Methylcompactin
• SIMVASTATIN IMPURITY, LOVASTATIN- [USP IMPURITY]
• Z754931258
• (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-8-(2-((4R,6R)-4-hydroxy-2-oxo-2H-pyran-6-yl)ethyl)-3,7-dimethylnaphtyl(S)-2-methylbutyrat
• (2S)-2-methylbutanoic acid [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-2-oxanyl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] ester
• (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-8-[2-((3R,5R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl ester
• [(1S,3R,7S,8S,8aR)-3,7-dimethyl-8-[2-[(2R,4R)-4-oxidanyl-6-oxidanylidene-oxan-2-yl]ethyl]-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
• 1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl 2-methylbutanoate
• 1S,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
• 8-[2-((2R,4R)-4-hydroxy-6-oxo(2H-3,4,5-trihydropyran-2-yl))ethyl](1S,7S,8S,3R, 8aR)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthyl (2S)-2-methylbutanoate
• 8-[2-(4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthale
• Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-- oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-
• BUTANOIC ACID, 2-METHYL-, 1,2,3,7,8,8A-HEXAHYDRO-3,7-DIMETHYL-8-(2-(TETRAHYDRO-4-HYDROXY-6-OXO-2H-PYRAN-2-YL)ETHYL)-1-NAPHTHALENYL ESTER, (1S-(1.ALPHA.(R*),3.ALPHA.,7.BETA.,8.BETA.(2S*,4S*),8.ALPHA..BETA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9806	98.06%
Caco-2	+	0.6717	67.17%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.9714	97.14%
Subcellular localzation	Mitochondria	0.6141	61.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7999	79.99%
OATP1B3 inhibitior	+	0.9618	96.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8498	84.98%
P-glycoprotein inhibitior	+	0.9117	91.17%
P-glycoprotein substrate	+	0.7834	78.34%
CYP3A4 substrate	+	0.6535	65.35%
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	+	0.9818	98.18%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7315	73.15%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9548	95.48%
Skin irritation	+	0.5493	54.93%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.5854	58.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8917	89.17%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.9750	97.50%
skin sensitisation	-	0.8532	85.32%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	III	0.6226	62.26%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	-	0.5614	56.14%
Glucocorticoid receptor binding	+	0.8448	84.48%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	-	0.6391	63.91%
Honey bee toxicity	-	0.8192	81.92%
Biodegradation	-	0.9250	92.50%
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	0.6 nM; 2.2 nM	Ki; IC50	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.34%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.97%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	94.41%	97.79%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.02%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.45%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.06%	96.09%
CHEMBL299	P17252	Protein kinase C alpha	91.03%	98.03%
CHEMBL221	P23219	Cyclooxygenase-1	90.73%	90.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.49%	96.47%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.05%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.03%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.60%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.32%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.73%	86.33%

Plants that contains it

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Cross-Links

• PubChem: 53232
• LOTUS: LTS0240572
• wikiData: Q417740