radicicol
naturalproductmech:mibig-7fc8631300 MINTED SEEDED enzyme inhibitor
Structure
| Standard InChIKey | WYZWZEOGROVVHK-UHFFFAOYSA-N |
|---|---|
| SMILES | CC1CC2OC2C=CC=CC(=O)CC2=C(C(O)=CC(O)=C2Cl)C(=O)O1 |
| Stereochemistry | undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers |
| Cross-references | npatlas:NPA03487, pubchem:6323491 |
Filing pathway
Polyketides — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is pks, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Pochonia chlamydosporia NCBITaxon:280754 |
SOURCE_ASSERTION | mibig:BGC0000134 | PMID:18567690 |
Occurrences 2
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Ilyonectria radicicola NCBITaxon:64609 |
LOTUS | DOI:10.1016/0040-4039(64)80029-0 |
| Metacordyceps chlamydosporia NCBITaxon:280754 |
LOTUS | DOI:10.1128/AEM.00478-08 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000134 | Pochonia chlamydosporia NCBITaxon:280754 |
CLUSTER_UNSTATED | genbank:EU520419.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Causal graph — bioactivity 4 nodes, 3 edges
Radicicol inhibits Saccharomyces cerevisiae HSP82 and engages human HSP90-alpha and HSP90-beta.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| radicicol | inhibits | Saccharomyces cerevisiae ATP-dependent molecular chaperone HSP82 | DOI:10.1016/j.chembiol.2004.03.033 |
| radicicol | binds | human heat shock protein HSP 90-alpha | DOI:10.1074/jbc.M113.533885 |
| radicicol | binds | human heat shock protein HSP 90-beta | DOI:10.1021/jm050355z |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Causal graph — bioactivity 2 nodes, 1 edges
Radicicol binds the Saccharolobus shibatae type II DNA topoisomerase VI subunit B ATPase.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| radicicol | binds | Saccharolobus shibatae TopoVI-B | DOI:10.1016/j.str.2007.12.020 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Molecular targets 9
| Target | Assay organism | Measurement | Reference |
|---|---|---|---|
| ATP-dependent molecular chaperone HSP82 UniProtKB:P02829 |
Saccharomyces cerevisiae (strain ATCC 204508 / S288c) NCBITaxon:559292 |
IC50 200 nM | PMID:15217611 |
| ATP-dependent molecular chaperone HSP82 UniProtKB:P02829 |
Saccharomyces cerevisiae (strain ATCC 204508 / S288c) NCBITaxon:559292 |
IC50 200 nM | PMID:17114002 |
| ATP-dependent molecular chaperone HSP82 UniProtKB:P02829 |
Saccharomyces cerevisiae (strain ATCC 204508 / S288c) NCBITaxon:559292 |
IC50 47 nM | PMID:17114002 |
| ATP-dependent molecular chaperone HSP82 UniProtKB:P02829 |
Saccharomyces cerevisiae (strain ATCC 204508 / S288c) NCBITaxon:559292 |
IC50 30 nM | PMID:17114002 |
| Heat shock protein HSP 90-alpha [1-236] UniProtKB:P07900 |
Homo sapiens NCBITaxon:9606 |
KD 46.3 nM | PMID:24356970 |
| Heat shock protein HSP 90-beta UniProtKB:P08238 |
Homo sapiens NCBITaxon:9606 |
IC50 150 nM | PMID:15974572 |
| Heat shock protein HSP 90-beta UniProtKB:P08238 |
Homo sapiens NCBITaxon:9606 |
IC50 150 nM | PMID:16202589 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial UniProtKB:Q15119 |
Homo sapiens NCBITaxon:9606 |
IC50 77800 nM | PMID:24356970 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial UniProtKB:Q15119 |
Homo sapiens NCBITaxon:9606 |
KD 18600 nM | PMID:24356970 |
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| Colorimetric Determination of ATPase Activity from Article 10.1016/j.chembiol.2004.03.033: "Structure-activity relationships in purine-based inhibitor binding to HSP90 isoforms." | IC50 0.2 uM | PMID:15217611 |
| Constitutive androstane receptor (CAR) small molecule agonists, cell-based qHTS assay in HepG2 cells | 0.3099 uM | pubchem.aid:2202728 |
| Constitutive androstane receptor (CAR) small molecule agonists, cell-based qHTS assay in HepG2 cells | 0.3099 uM | pubchem.aid:2202728 |
| Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB | IC50 400 uM | PMID:17683942 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 0.0027 uM | PMID:9925731 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 2 uM | PMID:18334211 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 715 uM | PMID:18440021 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 0.09 uM | PMID:19236053 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 0.019 uM | PMID:22573733 |
| FP Assay from Article 10.1016/j.chembiol.2006.09.015: "Inhibition of Hsp90 with synthetic macrolactones: synthesis and structural and biological evaluation of ring and conformational analogs of radicicol." | IC50 0.03 uM | PMID:17114002 |
| FP Assay from Article 10.1016/j.chembiol.2006.09.015: "Inhibition of Hsp90 with synthetic macrolactones: synthesis and structural and biological evaluation of ring and conformational analogs of radicicol." | IC50 0.047 uM | PMID:17114002 |
| Fluorescence Polarization (FP) Assay from Article 10.1016/j.bmcl.2005.08.092: "Structure-based discovery of a new class of Hsp90 inhibitors." | IC50 0.15 uM | PMID:16202589 |
| Fluorescence Polarization (FP) Assay from Article 10.1021/jm050355z: "Novel, potent small-molecule inhibitors of the molecular chaperone Hsp90 discovered through structure-based design." | IC50 0.15 uM | PMID:15974572 |
| Isothermal Titration Calorimetry (ITC) from Article 10.1074/jbc.M113.533885: "Structure-guided development of specific pyruvate dehydrogenase kinase inhibitors targeting the ATP-binding pocket." | KD 0.0463 uM | PMID:24356970 |
| Isothermal Titration Calorimetry (ITC) from Article 10.1074/jbc.M113.533885: "Structure-guided development of specific pyruvate dehydrogenase kinase inhibitors targeting the ATP-binding pocket." | KD 18.6 uM | PMID:24356970 |
| Malachite Green Assay from Article 10.1016/j.chembiol.2006.09.015: "Inhibition of Hsp90 with synthetic macrolactones: synthesis and structural and biological evaluation of ring and conformational analogs of radicicol." | IC50 0.2 uM | PMID:17114002 |
| P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 0.4375 uM | PMID:31515284 |
| P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 5.7016 uM | PMID:31515284 |
| PDK Inhibition Assay from Article 10.1074/jbc.M113.533885: "Structure-guided development of specific pyruvate dehydrogenase kinase inhibitors targeting the ATP-binding pocket." | IC50 77.8 uM | PMID:24356970 |
| Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) | 2.3576 uM | pubchem.aid:1964107 |
| Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) | 3.8482 uM | pubchem.aid:1964107 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 0.2747 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 0.2747 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 0.6397 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 0.6397 uM | pubchem.aid:1645877 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000134 | MIBIG | 3 |
This page is generated from data/natural_products/polyketides/radicicol.yaml, which is generated from the committed inventories. Neither is edited by hand.