3-Chloro-4-fluoro-N-(5-isopropylisoxazol-3-yl)benzamide

ID: ALA4089219

PubChem CID: 137643971

Max Phase: Preclinical

Molecular Formula: C13H12ClFN2O2

Molecular Weight: 282.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1cc(NC(=O)c2ccc(F)c(Cl)c2)no1

Standard InChI:  InChI=1S/C13H12ClFN2O2/c1-7(2)11-6-12(17-19-11)16-13(18)8-3-4-10(15)9(14)5-8/h3-7H,1-2H3,(H,16,17,18)

Standard InChI Key:  CHFQLBJFOFJEFR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   12.3415   -8.6505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1429   -8.4696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5587   -9.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0150   -9.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2642   -9.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5576   -9.8849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3718   -9.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8489   -8.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7141   -9.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8449   -9.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1423   -9.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4320   -9.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7299   -9.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7398  -10.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4575  -11.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1566  -10.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0378  -11.1522    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0174   -9.5158    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.8346   -8.6680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  1  5  2  0
  5  6  1  0
  7  8  1  0
  7  9  1  0
  3  7  1  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 13 18  1  0
 10 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089219

   ---

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: 282.70

Molecular Weight (Monoisotopic): 282.0571

AlogP: 3.84

#Rotatable Bonds: 3

Polar Surface Area: 55.13

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.73

CX Basic pKa: ┄

CX LogP: 3.86

CX LogD: 3.86

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.93

Np Likeness Score: -2.26

References

1. Rietz A, Li H, Quist KM, Cherry JJ, Lorson CL, Burnett BG, Kern NL, Calder AN, Fritsche M, Lusic H, Boaler PJ, Choi S, Xing X, Glicksman MA, Cuny GD, Androphy EJ, Hodgetts KJ..  (2017)  Discovery of a Small Molecule Probe That Post-Translationally Stabilizes the Survival Motor Neuron Protein for the Treatment of Spinal Muscular Atrophy.,  60  (11): [PMID:28481536] [10.1021/acs.jmedchem.6b01885]

Source

Source(1):

• Scientific Literature