UCSF

ZINC03780893

Draw Identity 99% 90% 80% 70%

Substance Information

In ZINC since Heavy atoms Benign functionality
September 26th, 2005 30 Yes

Popular Name: Simvastatin Simvastatin

Find On: PubMed — Wikipedia — Google

CAS Numbers: , 1002347-61-6 , 79902-63-9 , [79902-63-9]

Other Names:

(+)-Simvastatin; Cholestat; Denan; Eucor; Kolestevan; Lipex; Lipinorm; Liponorm; Lipovas; Lodales; Modutrol; Nor-Vastina; Pepstatin; Rechol; Simcor; Simovil; Simvastatin; Simvastatin lactone; Simvotin; Sinvacor; Sinvascor; Sivastin; Statin; Synvinolin; Va

(+)-Simvastatin;Cholestat;Denan;Eucor;Kolestevan;Lipex;Lipinorm;Liponorm;Lipovas;Lodales;Modutrol;Nor-Vastina;Pepstatin;Rechol;Simcor;Simovil;Simvastatin;Simvastatin lactone;Simvotin;Sinvacor;Sinvascor;Sivastin;Statin;Synvinolin;Valemia;Velostatin;Zocor;Z

(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 2,2-dimethylbutanoate

(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 2,2-dimethylbutanoate

(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 2,2-dimethylbutanoate

stat-

2,2-Dimethyl-butyric acid (1S,3R,7S,8S,8aR)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

2,2-Dimethylbutanoic 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

2,2-Dimethylbutyric 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

2,2-Dimethylbutyric 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; BRN 4768037; Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,*aR)-1,2,3,7,8,8a-hexahydro-

2,2-dimethylbutyric 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; MK-733; Simvastatin; Simvastatina; Simvastatine; Simvastatinum; Zocor

79902-63-9

79902-63-9; CPD000718785; SAM002589969; Simvastatin

79902-63-9; D00434; MK-733; Simvastatin (JP16/USP/INN); Zocor (TN)

79902-63-9; Prestwick_171; Simvastatin

8-[2-(4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl 2,2-dimethylbutanoate

AC-1530

AC1L1H1F

AKOS005111006

ARONIS24119

BAN

BCBcMAP01_000007

BIDD:GT0769

Bio-0672

BPBio1_001001

BRD-K22134346-001-05-8

BRN 4768037

BSPBio_000909

BSPBio_002337

Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,*aR)-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, 2,2-dimethyl-, (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, 2,2-dimethyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-

butanoic acid, 2,2-dimethyl-, (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, 2,2-dimethyl-, 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,3alpha,7beta,8beta(2S*,4S*),8abeta))-

butanoic acid, 2,2-dimethyl-,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,3 alpha,7 beta,8 beta(2S*,4S*),-8a beta

C25H38O5

CCRIS 7558

CHEBI:45577

CHEBI:9150

CHEMBL1064

Cholestat

CID54454

Coledis

Colemin

Corolin

CPD000718785

CPD000718785; SAM002589969; Simvastatin

CPD66-17; inactive simvastatin; simvastatin; simvastatin predrug; zocor

D00434

D019821

DAP000552

Denan

DivK1c_006991

DRG-0320

FDA

HMS1570N11

HMS1922H13

HMS2089D12

HMS2093E06

HSDB 7208

InChI=1/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1

INN

KBio1_001935

KBio2_002197

KBio2_004765

KBio2_007333

KBio3_001557

KBioGR_001244

KBioSS_002197

KS-1113

L 644128-000U

Labistatin

Lipex

Liponorm

Lipovas

Lodales

LS-46264

Medipo

MFCD00072007

MFCD06407575

MFCD09832920

MK 0733

MK 733

MK-0733

MK-733

MK733

MLS001304029

MLS001333077

MLS001333078

MLS002154038

MolPort-002-507-345

MolPort-002-885-862

NCGC00017324-01

NCGC00017324-02

NCGC00017324-03

nchembio790-comp16

Nivelipol

Pantok

Prestwick0_000865

Prestwick1_000865

Prestwick2_000865

Prestwick3_000865

Prestwick_171

QA-8441

Rendapid

RYMZZMVNJRMUDD-HGQWONQESA-

S1792_Selleck

S6196_SIGMA

SAM002589969

Simlup, Simcard, Simvacor, Simvoget, Zorced

Simovil

Simvast CR

Simvastatin & Primycin

Simvastatin (BAN

Simvastatin (FDA

Simvastatin (JAN/USP/INN)

Simvastatin (Zocor)

Simvastatin [Usan:Ban:Inn]

Simvastatin [USAN:INN:BAN]

Simvastatin, Compactin

Simvastatin-d3

Simvastatina

Simvastatina [Spanish]

Simvastatine

Simvastatine [French]

Simvastatinum

Simvastatinum [Latin]

Sinvacor

Sivastin

SMR000718785

SPBio_001881

SPBio_002830

SpecPlus_000895

SPECTRUM1504236

Spectrum2_001671

Spectrum3_000669

Spectrum4_000632

Spectrum5_001428

Spectrum_001717

STK801938

Synvinolin

TNP00259

UNII-AGG2FN16EV

USAN

USP)

Vasotenal

Velastatin

ZINC03780893

Zocor

Zocor (TN)

Zocor, Simlup, Simcard, Simvacor, Simvoget, Zorced, Simvastatin

Zocord

[(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] 2,2-dimethylbutanoate

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 4.76 11.51 -13.61 1 5 0 73 418.574 7 ↓

Vendor Notes

Note Type Comments Provided By
ALOGPS_SOLUBILITY 1.22e-02 g/l DrugBank-approved
MP 134 TCI
purity 9.500000000000000e+001 Enamine Building Blocks Enamine Building Blocks
Purity >98% APIChem
biological_use Antiarteriosclerotic IBScreen Bioactives IBScreen Bioactives
Indications antihypercholesterolemic KeyOrganics Bioactives
Therapy antihyperlipidemic, HMGCoA reductase inhibitor SMDC Iconix
mechanism Cholesterol synthesis inhibitor IBScreen Bioactives
mechanism Decreases LDL cholesterol levels, VLDL cholesterol levels and plasma triglycerides IBScreen Bioactives
Patent Database Links EP0814080; EP0940395; EP0987251; EP0992496; EP1036783; EP1055671; EP1127573; EP1254667; EP1258253; EP1284264; EP1325745; EP1438962; EP1452526; EP1452530; EP1479666; EP1491541; EP1510208; EP1510521; EP1514877; EP1520590; EP1533292; EP1533308; EP1541175; EP ChEBI
Target HMG-CoA Reductase Selleck Chemicals
mechanism HMG-CoA reductase inhibitor IBScreen Bioactives IBScreen Bioactives
mechanism Increases HDL cholesterol levels IBScreen Bioactives
UniProt Database Links LV1B1_LYCMC; LV1B2_LYCMC; LV1B_BUTOC; LV1B_BUTOS; LV1B_MESMA ChEBI
biological_source Metab. of Aspergillus terreus and Monascus spp.* ZereneX Building Blocks
PUBCHEM_SUBSTANCE_COMMENT NCC_SAMPLE_SUPPLIER : LightBiologicals; NCC_SUPPLIER_STRUCTURE_ID : S-9661; NCC_SUPPLIER_SAMPLE_COMMENTS : OFF-WHITE CRYSTALLINE POWDER NIH Clinical Collection via PubChem
Target Others Selleck Chemicals
PUBCHEM_SUBSTANCE_COMMENT SAMPLE_SUPPLIER: LightBiologicals; SUPPLIER_STRUCTURE_ID: S-9661; SUPPLIER_COMMENTS: OFF-WHITE CRYSTALLINE POWDER NIH Clinical Collection via PubChem
biological_use Used in the treatment of hypercholesterolaemia, and to reduce risk of death in patients with coronary heart disease and high serum cholesterol levels IBScreen Bioactives

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
HMDH-1-E HMG-CoA Reductase (cluster #1 Of 2), Eukaryotic Eukaryotes 4 0.39 Binding ≤ 10μM
HMDH-1-E HMG-CoA Reductase (cluster #1 Of 2), Eukaryotic Eukaryotes 12 0.37 Binding ≤ 10μM
HMDH-1-E HMG-CoA Reductase (cluster #1 Of 1), Eukaryotic Eukaryotes 12 0.37 Functional ≤ 10μM
Z80952-1-O HES (cluster #1 Of 1), Other Other 7 0.38 Functional ≤ 10μM
Z81020-2-O HepG2 (Hepatoblastoma Cells) (cluster #2 Of 8), Other Other 40 0.35 Functional ≤ 10μM
Z81135-1-O L6 (Skeletal Muscle Myoblast Cells) (cluster #1 Of 4), Other Other 27 0.35 Functional ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
HMDH_RAT P51639 HMG-CoA Reductase, Rat 18 0.36 Binding ≤ 1μM
HMDH_HUMAN P04035 HMG-CoA Reductase, Human 11 0.37 Binding ≤ 1μM
HMDH_RAT P51639 HMG-CoA Reductase, Rat 18 0.36 Binding ≤ 10μM
HMDH_HUMAN P04035 HMG-CoA Reductase, Human 11 0.37 Binding ≤ 10μM
Z81020 Z81020 HepG2 (Hepatoblastoma Cells) 40 0.35 Functional ≤ 10μM
Z80952 Z80952 HES 6.5 0.38 Functional ≤ 10μM
HMDH_HUMAN P04035 HMG-CoA Reductase, Human 12 0.37 Functional ≤ 10μM
Z81135 Z81135 L6 (Skeletal Muscle Myoblast Cells) 150 0.32 Functional ≤ 10μM

Reactome Annotations from Targets (via Uniprot)

Description Species
Activation of gene expression by SREBF (SREBP)
Cholesterol biosynthesis
PPARA activates gene expression

Analogs ( Draw Identity 99% 90% 80% 70% )