4-(2-(3,4-dichlorophenyl)acetamido)-N-(5-methylisoxazol-3-yl)benzamide

ID: ALA3108840

PubChem CID: 53255391

Max Phase: Preclinical

Molecular Formula: C19H15Cl2N3O3

Molecular Weight: 404.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NC(=O)c2ccc(NC(=O)Cc3ccc(Cl)c(Cl)c3)cc2)no1

Standard InChI:  InChI=1S/C19H15Cl2N3O3/c1-11-8-17(24-27-11)23-19(26)13-3-5-14(6-4-13)22-18(25)10-12-2-7-15(20)16(21)9-12/h2-9H,10H2,1H3,(H,22,25)(H,23,24,26)

Standard InChI Key:  UTTSAVIJOACRKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    5.5239   -6.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8137   -6.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1049   -6.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994   -6.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6879   -6.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887   -5.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983   -4.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1031   -5.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9752   -4.8633    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9742   -6.5154    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2335   -6.5082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9413   -6.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0699   -4.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6440   -6.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3549   -6.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3549   -5.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6440   -4.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9413   -5.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0668   -4.0453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7501   -2.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9336   -2.8362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7688   -3.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4782   -4.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0825   -3.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8852   -3.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5232   -5.2810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7788   -5.2751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  8  2  0
  6  9  1  0
  5 10  1  0
  2  3  1  0
 11  1  1  0
 11 12  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 12 18  2  0
 13 19  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 20 24  1  0
 24 25  1  0
 19 22  1  0
 16 13  1  0
  1 26  2  0
 13 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108840

   4-[[2-(3,4-dichlorophenyl)acetyl]amino]-N-(5-methyl-1,2-oxazol-3-yl)benzamide

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: 404.25

Molecular Weight (Monoisotopic): 403.0490

AlogP: 4.72

#Rotatable Bonds: 5

Polar Surface Area: 84.23

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.70

CX Basic pKa: ┄

CX LogP: 4.50

CX LogD: 4.50

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -2.15

References

1. Brimacombe KR, Walsh MJ, Liu L, Vásquez-Valdivieso MG, Morgan HP, McNae I, Fothergill-Gilmore LA, Michels PA, Auld DS, Simeonov A, Walkinshaw MD, Shen M, Boxer MB..  (2014)  Identification of ML251, a Potent Inhibitor of T. brucei and T. cruzi Phosphofructokinase.,  5  (1): [PMID:24900769] [10.1021/ml400259d]

Source

Source(1):

• Scientific Literature