rac-3-((5-bromo-4-(4-chlorophenyl)oxazol-2-yl)(pyridin-3-yl)methoxy)-2,6-difluorobenzamide

ID: ALA3098677

PubChem CID: 70980286

Max Phase: Preclinical

Molecular Formula: C22H13BrClF2N3O3

Molecular Weight: 520.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(F)ccc(OC(c2cccnc2)c2nc(-c3ccc(Cl)cc3)c(Br)o2)c1F

Standard InChI:  InChI=1S/C22H13BrClF2N3O3/c23-20-18(11-3-5-13(24)6-4-11)29-22(32-20)19(12-2-1-9-28-10-12)31-15-8-7-14(25)16(17(15)26)21(27)30/h1-10,19H,(H2,27,30)

Standard InChI Key:  MWLJSWIGWFXOMH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.1161  -18.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1150  -18.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8230  -19.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5327  -18.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5299  -18.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8212  -17.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4083  -17.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4081  -16.9465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7007  -18.1725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4069  -19.3997    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.8188  -16.9461    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.2360  -17.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9453  -18.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6514  -17.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4008  -18.0863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7354  -16.9438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5341  -16.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9441  -17.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8631  -16.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6768  -15.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0070  -15.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5246  -14.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7082  -14.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3818  -15.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7570  -17.5607    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.8538  -13.7833    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.9508  -18.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2431  -19.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2458  -20.2049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9556  -20.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6641  -20.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6578  -19.3810    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
 18 25  1  0
 22 26  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 13 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3098677

   3-((5-Bromo-4-(4-chlorophenyl)oxazol-2-yl)(pyridin-3-yl)methoxy)-2,6-difluorobenzamide

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: 520.72

Molecular Weight (Monoisotopic): 518.9797

AlogP: 5.70

#Rotatable Bonds: 6

Polar Surface Area: 91.24

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.95

CX Basic pKa: 4.64

CX LogP: 4.52

CX LogD: 4.52

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.35

Np Likeness Score: -1.17

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