Radicicol

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Radicicol
250px
Names
IUPAC name
(1aR,​2E,​4E,​14R,​15aR)-​8-​chloro-​9,​11-​dihydroxy-​14-​methyl-​1a,​14,​15,​15a-​tetrahydro-​6H-​oxireno​[e]​[2]​benzoxacyclotetradecine-​6,​12(7H)-​dione
Identifiers
12772-57-5 N
ChEBI CHEBI:556075 N
ChEMBL ChEMBL453386 N
ChemSpider 20137057 N
Jmol 3D model Interactive image
PubChem 6323491
  • 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 N
    Key: WYZWZEOGROVVHK-GTMNPGAYSA-N N
  • 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
    Key: WYZWZEOGROVVHK-GTMNPGAYBX
  • C[C@@H]1C[C@@H]2[C@H](O2)/C=C\C=C\C(=O)Cc3c(c(cc(c3Cl)O)O)C(=O)O1
Properties
C18H17ClO6
Molar mass 364.78 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Radicicol, also known as monorden, is a natural product that binds to Hsp90 (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, apoptosis, angiogenesis and oncogenesis.

Biosynthesis

Biosynthesis of Radicicol has been best studied in Pochonia chlamydosporia, in which the majority of the core structure is produced in vivo through iterative type I polyketide synthases.[1] 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.[2] 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.[3]

File:Proposed Radicicol Biosynthetic Pathway.png
Proposed biosynthetic pathway of Radicicol.

See also

Geldanamycin

References

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Further reading

  • Lua error in package.lua at line 80: module 'strict' not found. Review of the chemistry and biology of resorcylic acid lactones, including radicicol.


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