3-(2-oxo-5-(trifluoromethyl)benzo[d]oxazol-3(2H)-yl)propanoic acid

ID: ALA4093950

Cas Number: 893725-14-9

PubChem CID: 16636975

Max Phase: Preclinical

Molecular Formula: C11H8F3NO4

Molecular Weight: 275.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCn1c(=O)oc2ccc(C(F)(F)F)cc21

Standard InChI:  InChI=1S/C11H8F3NO4/c12-11(13,14)6-1-2-8-7(5-6)15(10(18)19-8)4-3-9(16)17/h1-2,5H,3-4H2,(H,16,17)

Standard InChI Key:  UOFLSFDYMYAREA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   32.5005  -20.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4994  -20.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2074  -21.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2056  -19.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9142  -20.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9190  -20.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6991  -21.0846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1764  -20.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6913  -19.7601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9936  -20.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9561  -21.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4128  -22.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6699  -23.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1266  -23.8570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4702  -23.4118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7913  -21.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0839  -20.8396    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.7907  -22.0659    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.0780  -21.6514    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  8 10  2  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093950

   2-Oxo-5-(trifluoromethyl)-3(2H)-benzoxazolepropanoic acid

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: 275.18

Molecular Weight (Monoisotopic): 275.0405

AlogP: 2.09

#Rotatable Bonds: 3

Polar Surface Area: 72.44

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.61

CX Basic pKa: ┄

CX LogP: 1.79

CX LogD: -1.55

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.93

Np Likeness Score: -1.44

References

1. Liddle J, Beaufils B, Binnie M, Bouillot A, Denis AA, Hann MM, Haslam CP, Holmes DS, Hutchinson JP, Kranz M, McBride A, Mirguet O, Mole DJ, Mowat CG, Pal S, Rowland P, Trottet L, Uings IJ, Walker AL, Webster SP..  (2017)  The discovery of potent and selective kynurenine 3-monooxygenase inhibitors for the treatment of acute pancreatitis.,  27  (9): [PMID:28336141] [10.1016/j.bmcl.2017.02.078]

Source

Source(1):

• Scientific Literature