Propyl 2-(4-(3,3,3-trifluoro-2,2-dimethylpropanoyloxy)benzamido)benzoate

ID: ALA3398159

PubChem CID: 118727255

Max Phase: Preclinical

Molecular Formula: C22H22F3NO5

Molecular Weight: 437.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOC(=O)c1ccccc1NC(=O)c1ccc(OC(=O)C(C)(C)C(F)(F)F)cc1

Standard InChI:  InChI=1S/C22H22F3NO5/c1-4-13-30-19(28)16-7-5-6-8-17(16)26-18(27)14-9-11-15(12-10-14)31-20(29)21(2,3)22(23,24)25/h5-12H,4,13H2,1-3H3,(H,26,27)

Standard InChI Key:  JROXMUKXHVGXGD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   10.3947    7.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3927    6.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3546    6.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933    5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924    6.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4914    5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915    3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    3.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548    3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7927    6.0049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0914    5.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6914    5.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0894    4.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7318    5.8461    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7295    4.6463    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.6893    4.0482    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -5.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
  4 11  2  0
  4 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 13 20  2  0
 13 21  1  0
 23  2  1  0
  2 24  1  0
 23 25  2  0
 22 23  1  0
 17 22  1  0
  6 21  1  0
 12 26  1  0
 24 27  1  0
 24 28  1  0
 24 29  1  0
 26 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3398159

   ---

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: 437.41

Molecular Weight (Monoisotopic): 437.1450

AlogP: 5.00

#Rotatable Bonds: 7

Polar Surface Area: 81.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.37

CX LogD: 6.37

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: -0.89

References

1. Hwang TL, Wang WH, Wang TY, Yu HP, Hsieh PW..  (2015)  Synthesis and pharmacological characterization of 2-aminobenzaldehyde oxime analogs as dual inhibitors of neutrophil elastase and proteinase 3.,  23  (5): [PMID:25650311] [10.1016/j.bmc.2014.12.056]

Source

Source(1):

• Scientific Literature