5-(4-(4-chlorophenoxy)phenyl)isoxazole-3-carboxylic acid

ID: ALA2323028

Cas Number: 925001-05-4

PubChem CID: 71625260

Max Phase: Preclinical

Molecular Formula: C16H10ClNO4

Molecular Weight: 315.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(-c2ccc(Oc3ccc(Cl)cc3)cc2)on1

Standard InChI:  InChI=1S/C16H10ClNO4/c17-11-3-7-13(8-4-11)21-12-5-1-10(2-6-12)15-9-14(16(19)20)18-22-15/h1-9H,(H,19,20)

Standard InChI Key:  UPFLMJBXADQZST-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   16.9285  -12.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9273  -12.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6354  -13.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3450  -12.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3422  -12.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6336  -11.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2207  -11.7545    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.0534  -13.3895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7605  -12.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4655  -13.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1721  -12.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1712  -12.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4579  -11.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7542  -12.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8759  -11.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6235  -12.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1685  -11.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7578  -10.7593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9590  -10.9316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9827  -11.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3172  -12.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4611  -10.8860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
 12 15  1  0
 20 21  1  0
 20 22  2  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2323028

   5-(4-(4-Chlorophenoxy)phenyl)isoxazole-3-carboxylic acid

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: 315.71

Molecular Weight (Monoisotopic): 315.0298

AlogP: 4.49

#Rotatable Bonds: 4

Polar Surface Area: 72.56

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.91

CX Basic pKa: ┄

CX LogP: 4.05

CX LogD: 0.84

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.77

Np Likeness Score: -1.13

References

1. Zhang M, Catrow JL, Ji H..  (2013)  High-Throughput Selectivity Assays for Small-Molecule Inhibitors of β-Catenin/T-Cell Factor Protein-Protein Interactions.,  4  (2): [PMID:24900664] [10.1021/ml300367f]

2. Catrow JL, Zhang Y, Zhang M, Ji H..  (2015)  Discovery of Selective Small-Molecule Inhibitors for the β-Catenin/T-Cell Factor Protein-Protein Interaction through the Optimization of the Acyl Hydrazone Moiety.,  58  (11): [PMID:25985283] [10.1021/acs.jmedchem.5b00223]

3. McCoy MA, Spicer D, Wells N, Hoogewijs K, Fiedler M, Baud MGJ..  (2022)  Biophysical Survey of Small-Molecule β-Catenin Inhibitors: A Cautionary Tale.,  65  (10.0): [PMID:35581674] [10.1021/acs.jmedchem.2c00228]

Source

Source(1):

• Scientific Literature