simvastatin (CHEBI:9150)

ChEBI > Main

CHEBI:9150 - simvastatin

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	simvastatin

ChEBI ID	CHEBI:9150

Definition	A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45577

Supplier Information	eMolecules:1934541, ZINC000004543732

Download	Molfile XML SDF

more structures >>

call loadScript javascripts\jsmol\core\package.js

call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode

call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js

Jmol JavaScript applet jmolApplet0_object__290488234008532__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__290488234008532__)

call loadScript javascripts\jsmol\core\corestate.z.js

viewerOptions:

{ "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9150","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__290488234008532__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"290488234008532","bgcolor":"#000" }

Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $

java.vendor: j2s

java.version: 0.0

os.name: j2s

Access: ALL

memory: 0.0/0.0

processors available: 1

useCommandThread: false

appletId:jmolApplet0_object (signed)

starting HoverWatcher_1

getValue emulate = null

defaults = "Jmol"

getValue boxbgcolor = null

getValue bgcolor = #000

backgroundColor = "#000"

getValue ANIMFRAMECallback = null

getValue APPLETREADYCallback = Jmol._readyCallback

APPLETREADYCallback = "Jmol._readyCallback"

getValue ATOMMOVEDCallback = null

getValue CLICKCallback = null

getValue ECHOCallback = null

getValue ERRORCallback = null

getValue EVALCallback = null

getValue HOVERCallback = null

getValue LOADSTRUCTCallback = null

getValue MEASURECallback = null

getValue MESSAGECallback = null

getValue MINIMIZATIONCallback = null

getValue PICKCallback = null

getValue RESIZECallback = null

getValue SCRIPTCallback = null

getValue SYNCCallback = null

getValue STRUCTUREMODIFIEDCallback = null

getValue doTranslate = null

language=en_US

getValue popupMenu = null

getValue script = null

Jmol applet jmolApplet0_object__290488234008532__ ready

call loadScript javascripts\jsmol\core\corescript.z.js

call loadScript javascripts\jsmol\J\script\FileLoadThread.js

starting QueueThread0_2

script 1 started

starting HoverWatcher_3

starting HoverWatcher_4

The Resolver thinks Mol

Mrv0541 02061413352D

starting HoverWatcher_5

Time for openFile(

Mrv0541 02061413352D

31 33 0 0 1 0 999 V2000

9.7549 -10.5607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

9.0453 -13.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

11.2141 -13.3702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

14.5595 -8.1909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0

10.5153 -12.1501 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0

11.9346 -11.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

9.0453 -11.0132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

9.7839 -12.5556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

11.2141 -12.5556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0

12.0396 -8.6109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

12.7456 -8.1909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

10.5153 -13.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

12.6153 -13.3702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

8.2089 -10.5642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

11.2286 -11.7301 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0

9.7839 -13.3702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0

13.2888 -12.1791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

9.4699 -11.7610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

12.7782 -10.6802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

11.2358 -8.2561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0

10.5479 -11.0639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0

11.9129 -12.1501 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0

13.4733 -9.4327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

12.6153 -12.5556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0

12.0396 -9.4327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0

7.2856 -11.0386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

12.7456 -9.8564 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0

13.4733 -8.6109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0

11.9129 -13.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

8.4243 -11.6253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

9.7803 -9.7243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0

9 3 1 0 0 0 0

9 5 1 0 0 0 0

7 14 1 0 0 0 0

27 23 1 0 0 0 0

28 4 1 6 0 0 0

1 31 2 0 0 0 0

8 16 1 0 0 0 0

3 12 2 0 0 0 0

12 16 1 0 0 0 0

29 13 2 0 0 0 0

24 13 1 0 0 0 0

7 18 1 0 0 0 0

9 15 1 1 0 0 0

14 26 1 0 0 0 0

27 25 1 0 0 0 0

3 29 1 0 0 0 0

9 22 1 0 0 0 0

7 30 1 0 0 0 0

25 10 1 0 0 0 0

5 8 1 0 0 0 0

21 1 1 0 0 0 0

27 19 1 1 0 0 0

10 20 2 0 0 0 0

10 11 1 0 0 0 0

28 11 1 0 0 0 0

6 19 1 0 0 0 0

5 21 1 6 0 0 0

16 2 1 6 0 0 0

1 7 1 0 0 0 0

22 24 1 0 0 0 0

23 28 1 0 0 0 0

22 6 1 1 0 0 0

24 17 1 1 0 0 0

M END): 17 ms

reading 31 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

31 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
[object Object]
Read full article at Wikipedia

Formula

C25H38O5

Net Charge

Average Mass

418.56620

Monoisotopic Mass

418.27192

InChI

InChI=1S/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

InChIKey

RYMZZMVNJRMUDD-HGQWONQESA-N

SMILES

CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@@H]12

Roles Classification
Biological Role(s):	EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor An EC 3.4.24.* (metalloendopeptidase) inhibitor that interferes with the action of anthrax lethal factor endopeptidase (EC 3.4.24.83). EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme. (via statin ) ferroptosis inducer Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.

Application(s):	prodrug A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. anticholesteremic drug A substance used to lower plasma cholesterol levels. (via statin )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	simvastatin (CHEBI:9150) has functional parent lovastatin (CHEBI:40303) simvastatin (CHEBI:9150) has role EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor (CHEBI:35664) simvastatin (CHEBI:9150) has role EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor (CHEBI:77255) simvastatin (CHEBI:9150) has role ferroptosis inducer (CHEBI:173085) simvastatin (CHEBI:9150) has role geroprotector (CHEBI:176497) simvastatin (CHEBI:9150) has role prodrug (CHEBI:50266) simvastatin (CHEBI:9150) is a δ-lactone (CHEBI:18946) simvastatin (CHEBI:9150) is a fatty acid ester (CHEBI:35748) simvastatin (CHEBI:9150) is a hexahydronaphthalenes (CHEBI:142348) simvastatin (CHEBI:9150) is a statin (semi-synthetic) (CHEBI:87633)

IUPAC Name

(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

INN	Source
simvastatin	DrugBank

Synonyms	Sources
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	ChemIDplus
MK-733	KEGG DRUG
Simvastatin	KEGG DRUG
Simvastatina	ChemIDplus
Simvastatine	ChemIDplus
Simvastatinum	ChemIDplus
Zocor	ChemIDplus

Manual Xrefs	Databases
2445	DrugCentral
D00434	KEGG DRUG
DB00641	DrugBank
EP33538	Patent
HMDB0005007	HMDB
LSM-2492	LINCS
Simvastatin	Wikipedia
US4444784	Patent
View more database links

Registry Numbers	Types	Sources
4768037	Beilstein Registry Number	Beilstein
79902-63-9	CAS Registry Number	KEGG DRUG
79902-63-9	CAS Registry Number	ChemIDplus

Citations	Types	Sources
11336576	PubMed citation	Europe PMC
12827636	PubMed citation	Europe PMC
14561068	PubMed citation	Europe PMC
14691614	PubMed citation	Europe PMC
14973129	PubMed citation	Europe PMC
16144183	PubMed citation	Europe PMC
17640385	PubMed citation	Europe PMC
18199328	PubMed citation	Europe PMC
18688862	PubMed citation	Europe PMC
18936176	PubMed citation	Europe PMC
22737247	PubMed citation	Europe PMC

Last Modified

28 October 2021

CHEBI:9150 - simvastatin

ChEBI is part of the ELIXIR infrastructure