Structure via PubChem · Public domain (PubChem)
Radicicol
Sign in to saveRadicicol, 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.
In the Vinony graph
Vinony's link graph records 7 inbound references to Radicicol, and connects out to digital object identifier, chemical formula and molar mass.
It sits within the topics Chembox image size set, Chlorine-containing natural products and Chloroarenes.
Vinony links it to 7 Wikipedia language editions.
Chemical data
- Formula
- C18H17ClO6
- Molecular weight
- 364.8 g/mol
- IUPAC name
- (4R,6R,8R,9Z,11E)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione
- SMILES
- C[C@@H]1C[C@@H]2[C@H](O2)/C=C\C=C\C(=O)CC3=C(C(=CC(=C3Cl)O)O)C(=O)O1
- InChIKey
- WYZWZEOGROVVHK-GTMNPGAYSA-N
- XLogP
- 3.4
- Polar surface area
- 96.4 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
547 papers- Development of radicicol analogues.Current cancer drug targets · 2003
- Hydrating for resistance to radicicol.ACS chemical biology · 2009
- Geldanamycin, radicicol, and chimeric inhibitors of the Hsp90 N-terminal ATP binding site.Current topics in medicinal chemistry · 2006
- Radicicol Inhibits Chikungunya Virus Replication by Targeting Nonstructural Protein 2.Antimicrobial agents and chemotherapy · 2021
- Radicicol - A multifaceted natural product with promising anticancer and anti-inflammatory activities: Insights into its mechanisms and therapeutic perspectives.Fitoterapia · 2026
via PubMed
Wikidata facts
- Subclass of
- macrolides
- Mass
- 364.0713659439999
Show 5 more facts
- canonical SMILES
- O=C1\C=C\C=C/C3OC3CC(C)OC(=O)c2c(O)cc(O)c(Cl)c2C1
- chemical formula
- C₁₈H₁₇ClO₆
- subject has role
- antimalarial
- isomeric SMILES
- C[C@@H]1C[C@@H]2[C@H](O2)/C=CC=CC(=O)Cc3c(c(cc(c3Cl)O)O)C(=O)O1
- inhibitor of
- heat shock protein Hsp90 family
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Biosynthesis
- See also
- References
- Further reading
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. 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. 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.
Excerpted from Wikipedia’s “Radicicol” article, available under the CC BY-SA 4.0 licence.