4-(3',5'-Dichloro-4'-hydroxy-3-biphenyl)-5-phenylisoxazole-3-carboxylic Acid

ID: ALA4217308

Chembl Id: CHEMBL4217308

PubChem CID: 145973093

Max Phase: Preclinical

Molecular Formula: C22H13Cl2NO4

Molecular Weight: 426.26

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(O)c1noc(-c2ccccc2)c1-c1cccc(-c2cc(Cl)c(O)c(Cl)c2)c1

Standard InChI:  InChI=1S/C22H13Cl2NO4/c23-16-10-15(11-17(24)20(16)26)13-7-4-8-14(9-13)18-19(22(27)28)25-29-21(18)12-5-2-1-3-6-12/h1-11,26H,(H,27,28)

Standard InChI Key:  HSUAKBVODMNSFP-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

    ALA4217308

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Associated Targets(Human)

PTPN1 Tchem Protein-tyrosine phosphatase 1B (8528 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DUSP3 Tchem Dual specificity protein phosphatase 3 (1161 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Cavia porcellus (23802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Phosphotyrosine-protein phosphatase PTPB (308 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ptbB Phosphotyrosine protein phosphatase (409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
J774.A1 (2436 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ptbB Phosphotyrosine protein phosphatase ptpB (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 426.26Molecular Weight (Monoisotopic): 425.0222AlogP: 6.39#Rotatable Bonds: 4
Polar Surface Area: 83.56Molecular Species: ACIDHBA: 4HBD: 2
#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski): 1
CX Acidic pKa: 3.85CX Basic pKa: CX LogP: 6.15CX LogD: 1.91
Aromatic Rings: 4Heavy Atoms: 29QED Weighted: 0.40Np Likeness Score: -0.41

References

1. Vickers CF, Silva APG, Chakraborty A, Fernandez P, Kurepina N, Saville C, Naranjo Y, Pons M, Schnettger LS, Gutierrez MG, Park S, Kreiswith BN, Perlin DS, Thomas EJ, Cavet JS, Tabernero L..  (2018)  Structure-Based Design of MptpB Inhibitors That Reduce Multidrug-Resistant Mycobacterium tuberculosis Survival and Infection Burden in Vivo.,  61  (18): [PMID:30153005] [10.1021/acs.jmedchem.8b00832]
2. Sahoo SK, Rani B, Gaikwad NB, Ahmad MN, Kaul G, Shukla M, Nanduri S, Dasgupta A, Chopra S, Yaddanapudi VM..  (2021)  Synthesis and structure-activity relationship of new chalcone linked 5-phenyl-3-isoxazolecarboxylic acid methyl esters potentially active against drug resistant Mycobacterium tuberculosis.,  222  [PMID:34116324] [10.1016/j.ejmech.2021.113580]

Source