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

ID: ALA4206173

PubChem CID: 145975895

Max Phase: Preclinical

Molecular Formula: C24H19NO4

Molecular Weight: 385.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2cccc(-c3c(C(=O)O)noc3-c3ccccc3)c2)cc(C)c1O

Standard InChI:  InChI=1S/C24H19NO4/c1-14-11-19(12-15(2)22(14)26)17-9-6-10-18(13-17)20-21(24(27)28)25-29-23(20)16-7-4-3-5-8-16/h3-13,26H,1-2H3,(H,27,28)

Standard InChI Key:  YJWODEWDNRBMBA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   31.4687   -5.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4676   -5.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1756   -6.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8853   -5.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8824   -5.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1738   -4.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1719   -3.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8315   -3.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5767   -2.6660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7595   -2.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5094   -3.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2768   -2.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6069   -1.2589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4644   -2.0944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7375   -3.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1286   -3.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3528   -3.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1847   -4.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7985   -4.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5720   -4.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7467   -2.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9161   -2.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3082   -1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5307   -1.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3646   -2.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9738   -3.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9213   -1.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4765   -0.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5889   -2.8382    0.0000 C   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
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  2  0
  6  7  1  0
 12 13  1  0
 12 14  2  0
 10 12  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 11 15  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 17 21  1  0
 24 27  1  0
 23 28  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4206173

   ---

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: 385.42

Molecular Weight (Monoisotopic): 385.1314

AlogP: 5.70

#Rotatable Bonds: 4

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: 3.85

CX Basic pKa: ┄

CX LogP: 5.97

CX LogD: 2.73

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: -0.29

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]

Source

Source(1):

• Scientific Literature