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VER-50589 - 10mM in DMSO, high purity , CAS No.747413-08-7

    Grade & Purity:
  • 10mM in DMSO
In stock
Item Number
V425808
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V425808-1ml
1ml
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$241.90

an isoxazole compound that inhibits Hsp90, a heat shock protein that acts as a molecular chaperone with roles in protein folding, cell signa

Basic Description

Synonyms VER-50589 | 747413-08-7 | 5-(5-Chloro-2,4-Dihydroxyphenyl)-N-Ethyl-4-(4-Methoxyphenyl)isoxazole-3-Carboxamide | VER50589 | CHEMBL252124 | 5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide | 5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl
Specifications & Purity 10mM in DMSO
Storage Temp Store at -80°C
Shipped In
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Product Description

VER-50589 is an isoxazole compound that inhibits Hsp90, a heat shock protein that acts as a molecular chaperone with roles in protein folding, cell signaling, and cancer.|VER-50589 is an isoxazole compound that has been shown to inhibit Hsp90 with an IC50 value of 21 nM. It produces a mean cellular antiproliferative GI50 value of 78 nM when tested against a human cancer cell line panel. Consistent with inhibition of Hsp90, VER-50589 has also been shown to induce the expression of HSP27 and Hsp72 while reducing the client proteins C-RAF, B-RAF, survivin, and PRMT5, causing cell cycle arrest and apoptosis. VER-50589 shows favorable pharmacokinetics and impairs tumor growth in animals. Importantly, glioblastoma cells do not acquire resistance to VER-50589 and resistance to other Hsp90 inhibitors does not produce cross-resistance to VER-50589.

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Benzenoids
Class Phenols
Subclass Benzenediols
Intermediate Tree Nodes Not available
Direct Parent Resorcinols
Alternative Parents Phenoxy compounds  P-chlorophenols  2-heteroaryl carboxamides  Anisoles  O-chlorophenols  Methoxybenzenes  1-hydroxy-2-unsubstituted benzenoids  Alkyl aryl ethers  Chlorobenzenes  Aryl chlorides  Isoxazoles  Heteroaromatic compounds  Secondary carboxylic acid amides  Oxacyclic compounds  Azacyclic compounds  Organic oxides  Organochlorides  Organonitrogen compounds  Organopnictogen compounds  Hydrocarbon derivatives  
Molecular Framework Aromatic heteromonocyclic compounds
Substituents 2-heteroaryl carboxamide - Phenoxy compound - Anisole - 2-chlorophenol - 2-halophenol - 4-halophenol - 4-chlorophenol - Phenol ether - Methoxybenzene - Resorcinol - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Halobenzene - Chlorobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Heteroaromatic compound - Azole - Isoxazole - Carboxamide group - Secondary carboxylic acid amide - Oxacycle - Azacycle - Carboxylic acid derivative - Organoheterocyclic compound - Ether - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Aromatic heteromonocyclic compound
Description This compound belongs to the class of organic compounds known as resorcinols. These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
External Descriptors Not available

Associated Targets(Human)

HSP90AA1 Tchem Heat shock protein HSP 90-alpha (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
HSP90AB1 Tchem Heat shock protein HSP 90-beta (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
HSP90AA1 Tchem Heat shock protein HSP 90-alpha (4115 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HSP90AB1 Tchem Heat shock protein HSP 90-beta (1689 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
DU-145 (51482 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SK-MEL-28 (48833 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HCT-116 (91556 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HepG2 (196354 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SF-268 (49410 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HSP90AA1 Tchem Heat shock protein HSP90 (3606 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name 5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-(4-methoxyphenyl)-1,2-oxazole-3-carboxamide
INCHI InChI=1S/C19H17ClN2O5/c1-3-21-19(25)17-16(10-4-6-11(26-2)7-5-10)18(27-22-17)12-8-13(20)15(24)9-14(12)23/h4-9,23-24H,3H2,1-2H3,(H,21,25)
InChIKey JXPCDMPJCKNLBY-UHFFFAOYSA-N
Smiles CCNC(=O)C1=NOC(=C1C2=CC=C(C=C2)OC)C3=CC(=C(C=C3O)O)Cl
Isomeric SMILES CCNC(=O)C1=NOC(=C1C2=CC=C(C=C2)OC)C3=CC(=C(C=C3O)O)Cl
PubChem CID 135446210
Molecular Weight 388.8

Certificates(CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Molecular Weight 388.800 g/mol
XLogP3 3.500
Hydrogen Bond Donor Count 3
Hydrogen Bond Acceptor Count 6
Rotatable Bond Count 5
Exact Mass 388.083 Da
Monoisotopic Mass 388.083 Da
Topological Polar Surface Area 105.000 Ų
Heavy Atom Count 27
Formal Charge 0
Complexity 502.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 0
Covalently-Bonded Unit Count 1

Solution Calculators

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