4-chloro-6-{5-[(2-morpholin-4-ylethyl)amino]-1,2-benzisoxazol-3-yl}benzene-1,3-diol

Identification

Name
4-chloro-6-{5-[(2-morpholin-4-ylethyl)amino]-1,2-benzisoxazol-3-yl}benzene-1,3-diol
Accession Number
DB07601
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 389.833
Monoisotopic: 389.11423385
Chemical Formula
C19H20ClN3O4
InChI Key
JLIRVZVVCCIAKG-UHFFFAOYSA-N
InChI
InChI=1S/C19H20ClN3O4/c20-15-10-13(16(24)11-17(15)25)19-14-9-12(1-2-18(14)27-22-19)21-3-4-23-5-7-26-8-6-23/h1-2,9-11,21,24-25H,3-8H2
IUPAC Name
4-chloro-6-(5-{[2-(morpholin-4-yl)ethyl]amino}-1,2-benzoxazol-3-yl)benzene-1,3-diol
SMILES
OC1=CC(O)=C(Cl)C=C1C1=NOC2=C1C=C(NCCN1CCOCC1)C=C2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHeat shock protein HSP 90-alphaNot AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
24836816
PubChem Substance
99444072
ChemSpider
22376941
BindingDB
20739
ChEBI
90529
ChEMBL
CHEMBL404630
HET
CXZ
PDB Entries
3bmy

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 Solubility0.227 mg/mLALOGPS
logP3.19ALOGPS
logP2.31ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)7.47ChemAxon
pKa (Strongest Basic)6.67ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.99 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity104.65 m3·mol-1ChemAxon
Polarizability39.65 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9846
Blood Brain Barrier+0.6858
Caco-2 permeable-0.6448
P-glycoprotein substrateSubstrate0.7358
P-glycoprotein inhibitor INon-inhibitor0.6443
P-glycoprotein inhibitor IIInhibitor0.8226
Renal organic cation transporterNon-inhibitor0.6681
CYP450 2C9 substrateNon-substrate0.8537
CYP450 2D6 substrateNon-substrate0.7347
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.5443
CYP450 2C9 inhibitorNon-inhibitor0.6662
CYP450 2D6 inhibitorNon-inhibitor0.7339
CYP450 2C19 inhibitorNon-inhibitor0.7404
CYP450 3A4 inhibitorNon-inhibitor0.5735
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6064
Ames testAMES toxic0.5528
CarcinogenicityNon-carcinogens0.7307
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6594 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8327
hERG inhibition (predictor II)Inhibitor0.6283
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 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 benzisoxazoles. These are aromatic compounds containing a benzene ring fused to an isoxazole ring. Isoxazole is five-membered ring with three carbon atoms, and an oxygen atom next to a nitrogen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzisoxazoles
Sub Class
Not Available
Direct Parent
Benzisoxazoles
Alternative Parents
Resorcinols / P-chlorophenols / O-chlorophenols / Secondary alkylarylamines / 1-hydroxy-2-unsubstituted benzenoids / Chlorobenzenes / Aryl chlorides / Morpholines / Isoxazoles / Heteroaromatic compounds
show 7 more
Substituents
Benzisoxazole / 4-chlorophenol / 2-chlorophenol / Resorcinol / 2-halophenol / 4-halophenol / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Secondary aliphatic/aromatic amine / Chlorobenzene
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tpr domain 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
HSP90AA1
Uniprot ID
P07900
Uniprot Name
Heat shock protein HSP 90-alpha
Molecular Weight
84659.015 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 September 15, 2010 15:24 / Updated on December 01, 2017 15:53