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

ID: ALA4214022

Chembl Id: CHEMBL4214022

PubChem CID: 138393064

Max Phase: Preclinical

Molecular Formula: C17H11Cl2NO4

Molecular Weight: 364.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1onc(C(=O)O)c1-c1cccc(-c2cc(Cl)c(O)c(Cl)c2)c1

Standard InChI:  InChI=1S/C17H11Cl2NO4/c1-8-14(15(17(22)23)20-24-8)10-4-2-3-9(5-10)11-6-12(18)16(21)13(19)7-11/h2-7,21H,1H3,(H,22,23)

Standard InChI Key:  RHLHXHOGVCAPFR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4214022

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 364.18

Molecular Weight (Monoisotopic): 363.0065

AlogP: 5.03

#Rotatable Bonds: 3

Polar Surface Area: 83.56

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.86

CX Basic pKa: ┄

CX LogP: 4.78

CX LogD: 0.54

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.68

Np Likeness Score: -0.66

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. Cazzaniga G, Mori M, Meneghetti F, Chiarelli LR, Stelitano G, Caligiuri I, Rizzolio F, Ciceri S, Poli G, Staver D, Ortore G, Tuccinardi T, Villa S..  (2022)  Virtual screening and crystallographic studies reveal an unexpected γ-lactone derivative active against MptpB as a potential antitubercular agent.,  234  [PMID:35286928] [10.1016/j.ejmech.2022.114235]

3. Cheng S, Wang Q, Chen X, Chen J, Wang B, Chen D, Shen D, Tian J, Ye F, Lu Y, Huang H, Lu Y, Zhang D..  (2022)  Discovery of biphenyls bearing thiobarbiturate fragment by structure-based strategy as Mycobacterium tuberculosis protein tyrosine phosphatase B inhibitors.,  73  [PMID:36150342] [10.1016/j.bmc.2022.117006]

Source

Source(1):

• Scientific Literature