Radicicol

Identification

Name
Radicicol
Accession Number
DB03758  (EXPT02763)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-294404 / RADICICOL R-2146
Categories
UNII
I60EH8GECX
CAS number
Not Available
Weight
Average: 364.777
Monoisotopic: 364.071365983
Chemical Formula
C18H17ClO6
InChI Key
WYZWZEOGROVVHK-GTMNPGAYSA-N
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
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
[H]/C1=C([H])\C(=O)CC2=C(C(O)=CC(O)=C2Cl)C(=O)O[C@]([H])(C)C[C@@]2([H])O[C@]2([H])/C([H])=C\1/[H]

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHeat shock protein HSP 90-betaNot AvailableHuman
UEndoplasminNot AvailableHuman
UDihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialNot AvailableHuman
U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 3, mitochondrialNot AvailableHuman
UVirulence sensor histidine kinase PhoQNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Radicicol.
PropacetamolThe serum concentration of Propacetamol can be increased when it is combined with Radicicol.
Food Interactions
Not Available

References

Synthesis Reference

Yukio Sugimura, Kimio Iino, Yoshio Tsujita, Yoko Shimada, Tomowo Kobayashi, Takeshi Kagasaki, "Radicicol derivatives, their preparation and their anti-tumor activity." U.S. Patent US5597846, issued September, 1979.

US5597846
General References
Not Available
External Links
PubChem Compound
6323491
PubChem Substance
46504837
ChemSpider
20137057
BindingDB
15361
ChEBI
556075
ChEMBL
CHEMBL414883
Therapeutic Targets Database
DNC001195
HET
RDC
Wikipedia
Radicicol
PDB Entries
1bgq / 1u0z / 2hkj / 2q8i / 2wer / 2zbk / 3cgy / 4egk

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.188 mg/mLALOGPS
logP3.22ALOGPS
logP3.68ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.02ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area96.36 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity93.56 m3·mol-1ChemAxon
Polarizability34.58 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9938
Blood Brain Barrier+0.9051
Caco-2 permeable+0.6021
P-glycoprotein substrateNon-substrate0.6299
P-glycoprotein inhibitor INon-inhibitor0.8888
P-glycoprotein inhibitor IINon-inhibitor0.9838
Renal organic cation transporterNon-inhibitor0.9069
CYP450 2C9 substrateNon-substrate0.827
CYP450 2D6 substrateNon-substrate0.8152
CYP450 3A4 substrateNon-substrate0.5578
CYP450 1A2 substrateNon-inhibitor0.7194
CYP450 2C9 inhibitorNon-inhibitor0.7904
CYP450 2D6 inhibitorNon-inhibitor0.9256
CYP450 2C19 inhibitorNon-inhibitor0.8108
CYP450 3A4 inhibitorNon-inhibitor0.8086
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9777
Ames testNon AMES toxic0.6926
CarcinogenicityNon-carcinogens0.9116
BiodegradationNot ready biodegradable0.9858
Rat acute toxicity2.4787 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7902
hERG inhibition (predictor II)Non-inhibitor0.9691
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Hydroxybenzoic acid derivatives
Alternative Parents
1-hydroxy-2-unsubstituted benzenoids / Aryl chlorides / Vinylogous acids / Lactones / Cyclic ketones / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Epoxides / Dialkyl ethers
show 3 more
Substituents
Dihydroxybenzoic acid / 1-hydroxy-2-unsubstituted benzenoid / Aryl chloride / Aryl halide / Vinylogous acid / Carboxylic acid ester / Ketone / Cyclic ketone / Lactone / Carboxylic acid derivative
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cyclic ketone, epoxide, phenols, macrolide antibiotic, enone, monochlorobenzenes (CHEBI:556075)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Utp binding
Specific Function
Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Under...
Gene Name
HSP90AB1
Uniprot ID
P08238
Uniprot Name
Heat shock protein HSP 90-beta
Molecular Weight
83263.475 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Virion binding
Specific Function
Molecular chaperone that functions in the processing and transport of secreted proteins. When associated with CNPY3, required for proper folding of Toll-like receptors (By similarity). Functions in...
Gene Name
HSP90B1
Uniprot ID
P14625
Uniprot Name
Endoplasmin
Molecular Weight
92468.06 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Dihydrolipoyllysine-residue acetyltransferase activity
Specific Function
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name
DLAT
Uniprot ID
P10515
Uniprot Name
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial
Molecular Weight
68996.03 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Pyruvate dehydrogenase (acetyl-transferring) kinase activity
Specific Function
Inhibits pyruvate dehydrogenase activity by phosphorylation of the E1 subunit PDHA1, and thereby regulates glucose metabolism and aerobic respiration. Can also phosphorylate PDHA2. Decreases glucos...
Gene Name
PDK3
Uniprot ID
Q15120
Uniprot Name
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial
Molecular Weight
46938.485 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Member of the two-component regulatory system PhoP/PhoQ which regulates the expression of genes involved in virulence, adaptation to acidic and low Mg(2+) environments and resistance to host defense antimicrobial peptides. Essential for intramacrophage survival of S.typhimurium. In low periplasmic Mg(2+), PhoQ functions as a membrane-associated protein kinase that undergoes autophosphorylation and subsequently transfers the phosphate to PhoP, resulting in the expression of PhoP-activated genes (PAG) and repression of PhoP-repressed genes (PRG). In high periplasmic Mg(2+), acts as a protein phosphatase that dephosphorylates phospho-PhoP, resulting in the repression of PAG and may lead to expression of some PRG. Essential for transcription of spiC inside macrophages by controlling the expression of the two-component regulatory system SsrB/SpiR (SsrA) and Pir at transcriptional and post-transcriptional levels respectively. Promotes expression of the two-component regulatory system PmrA/PmrB via activation of pmrD gene. Is required to attenuate bacterial growth within fibroblast cells and to enhance bacterial resistance to bile in intestinal cells. Negatively regulates prgH, which is required for invasion of epithelial cells. Involved in acid tolerance.
Specific Function
Atp binding
Gene Name
phoQ
Uniprot ID
P0DM80
Uniprot Name
Virulence sensor histidine kinase PhoQ
Molecular Weight
55466.19 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:43