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

ID: ALA3098678

PubChem CID: 66574789

Max Phase: Preclinical

Molecular Formula: C20H14BrF5N2O4

Molecular Weight: 521.24

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H14BrF5N2O4/c21-17-16(9-1-3-10(4-2-9)20(24,25)26)28-19(32-17)13(7-8-29)31-12-6-5-11(22)14(15(12)23)18(27)30/h1-6,13,29H,7-8H2,(H2,27,30)

Standard InChI Key:  LGROMENIPXXFFI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   21.8399  -18.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8387  -19.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5468  -19.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2564  -19.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2536  -18.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5450  -17.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1321  -17.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1319  -17.1157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4245  -18.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1307  -19.5689    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.5425  -17.1153    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.9598  -17.9265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6690  -18.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3752  -17.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1246  -18.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4592  -17.1130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2578  -16.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6678  -17.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5869  -16.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4006  -16.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7308  -15.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2484  -14.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4320  -14.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1055  -15.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5776  -13.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3899  -13.8637    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.0944  -13.2935    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.7845  -13.1576    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.4808  -17.7299    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   24.6721  -19.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9659  -19.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9690  -20.3781    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA3098678

   3-[1-[5-Bromo-4-[4-(trifluoromethyl)phenyl]oxazol-2-yl]-3-hydroxy-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: 521.24

Molecular Weight (Monoisotopic): 520.0057

AlogP: 5.00

#Rotatable Bonds: 7

Polar Surface Area: 98.58

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.96

CX Basic pKa: ┄

CX LogP: 3.65

CX LogD: 3.65

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -0.75

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