radicicol (CHEBI:556075)

ChEBI > Main

CHEBI:556075 - radicicol

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	radicicol

ChEBI ID	CHEBI:556075

Definition	An antifungal macrolactone antibiotic, obtained from Diheterospora chlamydosporia and Chaetomium chiversii that inhibits protein tyrosine kinase and heat shock protein 90 (Hsp90).

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

Secondary ChEBI IDs	CHEBI:47652, CHEBI:47650, CHEBI:68728

Supplier Information	ChemicalBook:CB62507657, ChemicalBook:CB12470923, Selleckchem:BIBW2992, ZINC000003976838

Download	Molfile XML SDF

more structures >>

Molfile

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__173436703950156__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__173436703950156__)

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

viewerOptions:

{ "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do;jsessionid=4541AEEA4D664C013D7F91B098E6A07F?chebiId=556075","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__173436703950156__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"173436703950156","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__173436703950156__ 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

Marvin 10121214153D

starting HoverWatcher_5

Time for openFile(

Marvin 10121214153D

42 44 0 0 0 0 999 V2000

-1.2100 0.1710 -0.4070 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0810 0.0960 1.0550 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.1890 -0.2290 1.8520 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.0510 -0.2960 3.2280 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.8200 -0.0430 3.8140 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2800 0.2810 3.0260 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1550 0.3530 1.6580 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3430 0.7090 0.8040 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2410 -0.4890 0.6520 C 0 0 0 0 0 0 0 0 0 0 0 0

2.6820 -0.8860 -0.6240 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2140 -0.2620 -1.7350 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7070 -0.6460 -3.0540 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1380 -0.1630 -4.1610 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9610 0.7720 -4.0670 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.4170 0.1540 -3.8180 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.4150 0.9550 -2.9810 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.5040 0.0180 -2.4510 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.3290 -1.3700 -3.0700 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3930 -0.0770 -1.0050 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.2420 0.4610 -1.0830 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.3920 -0.4770 1.2760 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.6890 -0.1110 5.1640 O 0 0 0 0 0 0 0 0 0 0 0 0

1.8160 0.5960 3.7720 Cl 0 0 0 0 0 0 0 0 0 0 0 0

2.5870 -1.1150 1.6330 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.0330 0.6860 -5.0880 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.9020 -0.5460 3.8440 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8980 1.5200 1.2750 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9990 1.0310 -0.1780 H 0 0 0 0 0 0 0 0 0 0 0 0

3.3930 -1.6940 -0.7210 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4750 0.5190 -1.6410 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5440 -1.3250 -3.1370 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5260 -0.4440 -5.1310 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1620 1.7470 -3.6260 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4680 -0.9290 -3.7140 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8710 1.7280 -3.6000 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8960 1.4190 -2.1430 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.4840 0.4130 -2.7150 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4120 -1.8230 -2.6920 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1800 -1.9960 -2.8040 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2690 -1.2790 -4.1550 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.8560 0.3690 1.2230 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8780 0.7720 5.5080 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 19 1 0 0 0 0

1 20 2 0 0 0 0

2 3 4 0 0 0 0

2 7 4 0 0 0 0

3 4 4 0 0 0 0

3 21 1 0 0 0 0

4 5 4 0 0 0 0

4 26 1 0 0 0 0

5 6 4 0 0 0 0

5 22 1 0 0 0 0

6 7 4 0 0 0 0

6 23 1 0 0 0 0

7 8 1 0 0 0 0

8 9 1 0 0 0 0

8 27 1 0 0 0 0

8 28 1 0 0 0 0

9 10 1 0 0 0 0

9 24 2 0 0 0 0

10 11 2 0 0 0 0

10 29 1 0 0 0 0

11 12 1 0 0 0 0

11 30 1 0 0 0 0

12 13 2 0 0 0 0

12 31 1 0 0 0 0

13 14 1 0 0 0 0

13 32 1 0 0 0 0

14 15 1 0 0 0 0

14 25 1 0 0 0 0

14 33 1 0 0 0 0

15 16 1 0 0 0 0

15 25 1 0 0 0 0

15 34 1 0 0 0 0

16 17 1 0 0 0 0

16 35 1 0 0 0 0

16 36 1 0 0 0 0

17 18 1 0 0 0 0

17 19 1 0 0 0 0

17 37 1 0 0 0 0

18 38 1 0 0 0 0

18 39 1 0 0 0 0

18 40 1 0 0 0 0

21 41 1 0 0 0 0

22 42 1 0 0 0 0

M END): 23 ms

reading 42 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

42 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Leflunomide, sold under the brand name Arava among others, is an immunosuppressive disease-modifying antirheumatic drug (DMARD), used in active moderate-to-severe rheumatoid arthritis and psoriatic arthritis. It is a pyrimidine synthesis inhibitor that works by inhibiting dihydroorotate dehydrogenase.
Read full article at Wikipedia

Formulae

C18H17ClO6
C18H17ClO6

Net Charge

Average Mass

364.77700

Monoisotopic Mass

364.07137

InChI

InChI=1S/C18H17ClO6/c1-9-6-15-14(25-15)5-3-2-4-10(20)7-11-16(18(23)24-9)12(21)8-13(22)17(11)19/h2-5,8-9,14-15,21-22H,6-7H2,1H3/b4-2+,5-3-/t9-,14-,15-/m1/s1

InChIKey

WYZWZEOGROVVHK-GTMNPGAYSA-N

SMILES

C[C@@H]1C[C@H]2O[C@@H]2\C=C/C=C/C(=O)Cc2c(Cl)c(O)cc(O)c2C(=O)O1

Metabolite of Species	Details
Chaetomium chiversii (NCBI:txid155873)	See: PubMed

Roles Classification
Biological Role(s):	tyrosine kinase inhibitor Any protein kinase inhibitor that interferes with the action of tyrosine kinase. antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via macrolide antibiotic )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	radicicol (CHEBI:556075) has role antifungal agent (CHEBI:35718) radicicol (CHEBI:556075) has role metabolite (CHEBI:25212) radicicol (CHEBI:556075) has role tyrosine kinase inhibitor (CHEBI:38637) radicicol (CHEBI:556075) is a cyclic ketone (CHEBI:3992) radicicol (CHEBI:556075) is a enone (CHEBI:51689) radicicol (CHEBI:556075) is a epoxide (CHEBI:32955) radicicol (CHEBI:556075) is a macrolide antibiotic (CHEBI:25105) radicicol (CHEBI:556075) is a monochlorobenzenes (CHEBI:83403) radicicol (CHEBI:556075) is a phenols (CHEBI:33853)

IUPAC Name

(1aR,2Z,4E,14R,15aR)-8-chloro-9,11-dihydroxy-14-methyl-1a,14,15,15a-tetrahydro-6H-oxireno[e][2]benzoxacyclotetradecine-6,12(7H)-dione

Synonyms	Sources
Monorden	ChemIDplus
RADICICOL	PDBeChem

Manual Xrefs	Databases
DB03758	DrugBank
Radicicol	Wikipedia
RDC	PDBeChem
View more database links

Registry Numbers	Types	Sources
12772-57-5	CAS Registry Number	ChemIDplus
15865423	Reaxys Registry Number	Reaxys

Citations

Last Modified

24 October 2014

CHEBI:556075 - radicicol

ChEBI is part of the ELIXIR infrastructure