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Revision as of 12:30, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 463300857 of page Radicicol for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').		Latest revision as of 14:19, 23 December 2023 edit Equinox (talk | contribs)Extended confirmed users18,277 editsmNo edit summary
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			{{Chembox
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			| Verifiedfields = changed
	{{chembox
			| Watchedfields = changed
	| verifiedrevid = 401038937		| verifiedrevid = 464379673
	| ImageFile = Radicicol Winssinger et al.svg		| ImageFile = Radicicol Winssinger et al.svg
	| ImageSize = 250		| ImageSize = 250
	| IUPACName = (1a''R'',​2''E'',​4''E'',​14''R'',​15a''R'')-​8-​chloro-​9,​11-​dihydroxy-​14-​methyl-​1a,​14,​15,​15a-​tetrahydro-​6''H''-​oxireno​​​benzoxacyclotetradecine-​6,​12(7''H'')-​dione		| PIN = (1a''R'',2''E'',4''E'',14''R'',15a''R'')-8-Chloro-9,11-dihydroxy-14-methyl-1a,14,15,15a-tetrahydro-6''H''-oxirenobenzoxacyclotetradecine-6,12(7''H'')-dione
	| OtherNames =		| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| Abbreviations =		| Abbreviations =
		⚫	| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫	| 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-
		⚫	| ChemSpiderID = 20137057
⚫	| InChIKey = WYZWZEOGROVVHK-HZDAAVBUBT
			| SMILES = C1C2(O2)/C=C\C=C\C(=O)Cc3c(c(cc(c3Cl)O)O)C(=O)O1
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 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-		| InChI = 1/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-GTMNPGAYBX
⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫	| StdInChIKey = WYZWZEOGROVVHK-HZDAAVBUSA-N
		⚫	| StdInChI = 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
	| InChIKey1 = WYZWZEOGROVVHK-HZDAAVBUSA-N
		⚫	| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫	| CASNo = <!-- blanked - oldvalue: 12772-57-5 -->
		⚫	| StdInChIKey = WYZWZEOGROVVHK-GTMNPGAYSA-N
⚫	| CASNo_Ref ={{cascite|??|??}}
		⚫	| CASNo = 12772-57-5
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = I60EH8GECX
	| EINECS =		| EINECS =
	| PubChem = 6323491		| PubChem = 6323491
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| ChEMBL = <!-- blanked - oldvalue: 453386 -->
			| ChEMBL = 453386
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| ChemSpiderID=16735913
	| SMILES = O=C1\C=C\C=C/C3OC3CC(C)OC(=O)c2c(O)cc(O)c(Cl)c2C1
	| InChI =
	| RTECS =		| RTECS =
	| MeSHName =		| MeSHName =
			| ChEBI_Ref = {{ebicite|changed|EBI}}
	| ChEBI =		| ChEBI = 556075
	| KEGG =		| KEGG =
			}}
	| ATCCode = }}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| MolarMass =		| MolarMass =
	| C=18|H=17|Cl=1|O=6		| C=18 | H=17 | Cl=1 | O=6
	| Appearance =		| Appearance =
	| Density =		| Density =
	| MeltingPt =		| MeltingPt =
	| Melting_notes =		| MeltingPt_notes =
	| BoilingPt =		| BoilingPt =
	| Boiling_notes =		| BoilingPt_notes =
	| Solubility =		| Solubility =
	| SolubleOther =		| SolubleOther =
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	| RefractIndex =		| RefractIndex =
	| Viscosity =		| Viscosity =
	| Dipole = }}		| Dipole =
			}}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| CrystalStruct =		| CrystalStruct =
	| Coordination =		| Coordination =
	| MolShape =		| MolShape =
	| Dipole = }}		| Dipole =
			}}
	| Section4 = {{Chembox Thermochemistry		|Section4={{Chembox Thermochemistry
	| DeltaHf =		| DeltaHf =
	| DeltaHc =		| DeltaHc =
	| Entropy =		| Entropy =
	| HeatCapacity = }}		| HeatCapacity =
			}}
	| Section5 = {{Chembox Pharmacology		|Section5={{Chembox Pharmacology
	| AdminRoutes =		| AdminRoutes =
	| Bioavail =		| Bioavail =
	| Metabolism =		| Metabolism =
	| HalfLife =		| HalfLife =
	| ProteinBound		| ProteinBound =
	| Excretion =		| Excretion =
	| Legal_status =		| Legal_status =
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	| Legal_AU =		| Legal_AU =
	| Legal_CA =		| Legal_CA =
	| PregCat =		| Pregnancy_category =
	| PregCat_AU =		| Pregnancy_AU =
	| PregCat_US = }}		| Pregnancy_US =
			}}
	| Section6 = {{Chembox Explosive		|Section6={{Chembox Explosive
	| ShockSens =		| ShockSens =
	| FrictionSens =		| FrictionSens =
	| ExplosiveV =		| DetonationV =
	| REFactor = }}		| REFactor =
			}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| EUClass =
	| EUIndex =
	| MainHazards =		| MainHazards =
	| NFPA-H =		| NFPA-H =
	| NFPA-F =		| NFPA-F =
	| NFPA-R =		| NFPA-R =
	| NFPA-O =		| NFPA-S =
	| RPhrases =		| HPhrases =
	| SPhrases =		| PPhrases =
	| RSPhrases =		| GHS_ref =
	| FlashPt =		| FlashPt =
	| Autoignition =		| AutoignitionPt =
	| ExploLimits =		| ExploLimits =
	| PEL = }}		| PEL =
			}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| OtherAnions =		| OtherAnions =
	| OtherCations =		| OtherCations =
	| OtherFunctn =		| OtherFunction =
	| Function =		| OtherFunction_label =
	| OtherCpds = }}		| OtherCompounds =
			}}
	}}		}}
			'''Radicicol''', also known as '''monorden''', is a natural product that binds to ] (Heat Shock Protein 90) and alters its function. HSP90 client proteins play important roles in the regulation of the cell cycle, cell growth, cell survival, ], ] and ].
			== Biosynthesis ==
			Biosynthesis of radicicol has been best studied in '']'', in which the majority of the core structure is produced in vivo through iterative type I ].<ref>{{cite journal | doi = 10.1074/jbc.M110.183574 | volume=285 | title=Insights into Radicicol Biosynthesis via Heterologous Synthesis of Intermediates and Analogs | journal=Journal of Biological Chemistry | pages=41412–41421 | pmid=20961859 | pmc=3009867 | vauthors=Zhou H, Qiao K, Gao Z, Vederas JC, Tang Y| year=2010 | issue=53 | doi-access=free }}</ref> This structure produced is the earliest intermediate in the radicicol biosynthesis, monocillin II. This intermediate is transformed to radicicol through halogenation and epoxide formation performed by RadH and RadP respectively.<ref name=Wang>{{cite journal | doi = 10.1016/j.chembiol.2008.10.006 | volume=15 | title=Functional Characterization of the Biosynthesis of Radicicol, an Hsp90 Inhibitor Resorcylic Acid Lactone from Chaetomium chiversii | journal= Chemistry & Biology| year=2008 | pages=1328–1338| doi-access=free | last1=Wang | first1=Shuhao | last2=Xu | first2=Yuquan | last3=Maine | first3=Erin A. | last4=Wijeratne | first4=E.M. Kithsiri | last5=Espinosa-Artiles | first5=Patricia | last6=Gunatilaka | first6=A.A. Leslie | last7=Molnár | first7=István | issue=12 | pmid=19101477 }}</ref> These enzymes are coded by the genes Rdc2 and Rdc4 in the pathway, and removing either of these results in a product that has the monocillin II core, but does not have either the epoxide or halogen added.<ref name=Wang/>
			]{{clear left}}
			== See also ==
			* ]
			== References ==
			<references />
			==Further reading==
			*{{cite journal |vauthors=Winssinger N, Barluanga S |title=Chemistry and biology of resorcylic acid lactones |journal=Chem Commun |volume= 13|issue=1 |pages=22–36 |date=January 2007 |doi=10.1039/B610344H |pmid=17279252 }} Review of the chemistry and biology of resorcylic acid lactones, including radicicol.
			]
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