rac-3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-(dimethylamino)propoxy)-2,6-difluorobenzamide

ID: ALA3098679

PubChem CID: 72947705

Max Phase: Preclinical

Molecular Formula: C22H19BrF5N3O3

Molecular Weight: 548.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCC(Oc1ccc(F)c(C(N)=O)c1F)c1nc(-c2ccc(C(F)(F)F)cc2)c(Br)o1

Standard InChI:  InChI=1S/C22H19BrF5N3O3/c1-31(2)10-9-15(33-14-8-7-13(24)16(17(14)25)20(29)32)21-30-18(19(23)34-21)11-3-5-12(6-4-11)22(26,27)28/h3-8,15H,9-10H2,1-2H3,(H2,29,32)

Standard InChI Key:  QOAOOBLEORARMS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.1530   -6.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1519   -6.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599   -7.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696   -6.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -6.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8581   -5.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4452   -5.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4450   -4.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7376   -6.1499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4438   -7.3771    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557   -4.9235    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2729   -5.7347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9821   -6.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6883   -5.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4377   -6.0637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7723   -4.9212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5709   -4.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9809   -5.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000   -4.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7137   -3.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0439   -3.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5615   -2.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7451   -2.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4186   -3.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8907   -1.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7030   -1.6718    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.4076   -1.1016    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0976   -0.9658    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7939   -5.5380    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -6.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2791   -7.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2821   -8.1862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760   -8.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9914   -8.5922    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
  1  7  1  0
  7  8  2  0
  7  9  1  0
  2 10  1  0
  6 11  1  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 18  1  0
 17 16  1  0
 16 14  2  0
 17 18  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 17 19  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 18 29  1  0
 13 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3098679

   3-(1-(5-Bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-(dimethylamino)propoxy)-2,6-difluoro-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: 548.31

Molecular Weight (Monoisotopic): 547.0530

AlogP: 5.57

#Rotatable Bonds: 8

Polar Surface Area: 81.59

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.96

CX Basic pKa: 8.66

CX LogP: 4.36

CX LogD: 3.08

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.37

Np Likeness Score: -1.01

References

1. Stokes NR, Baker N, Bennett JM, Chauhan PK, Collins I, Davies DT, Gavade M, Kumar D, Lancett P, Macdonald R, Macleod L, Mahajan A, Mitchell JP, Nayal N, Nayal YN, Pitt GR, Singh M, Yadav A, Srivastava A, Czaplewski LG, Haydon DJ..  (2014)  Design, synthesis and structure-activity relationships of substituted oxazole-benzamide antibacterial inhibitors of FtsZ.,  24  (1): [PMID:24287381] [10.1016/j.bmcl.2013.11.002]

Source

Source(1):

• Scientific Literature