(S)-5-chloro-2-hydroxy-N-(3-methyl-1-oxo-1-(4-(trifluoromethyl)phenylamino)butan-2-yl)benzamide

ID: ALA2425560

PubChem CID: 46861971

Max Phase: Preclinical

Molecular Formula: C19H18ClF3N2O3

Molecular Weight: 414.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](NC(=O)c1cc(Cl)ccc1O)C(=O)Nc1ccc(C(F)(F)F)cc1

Standard InChI:  InChI=1S/C19H18ClF3N2O3/c1-10(2)16(25-17(27)14-9-12(20)5-8-15(14)26)18(28)24-13-6-3-11(4-7-13)19(21,22)23/h3-10,16,26H,1-2H3,(H,24,28)(H,25,27)/t16-/m0/s1

Standard InChI Key:  SMJZGDRVSORQDF-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   17.8941  -18.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8930  -19.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6077  -19.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3242  -19.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3213  -18.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6059  -18.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0392  -19.9837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0342  -18.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7502  -18.7364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0311  -17.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4631  -18.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1791  -18.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8920  -18.3158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1823  -19.5561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6080  -18.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6082  -19.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3234  -19.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0373  -19.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0315  -18.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3158  -18.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1795  -18.3331    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.4601  -17.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1729  -17.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7440  -17.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7538  -19.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7581  -20.7790    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.4662  -19.5379    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.4662  -20.3663    0.0000 F   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
  4  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 21  1  0
 11 22  1  1
 22 23  1  0
 22 24  1  0
 18 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2425560

   5-chloro-2-hydroxy-N-[(1S)-2-methyl-1-[[4-(trifluoromethyl)phenyl]carbamoyl]propyl]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: 414.81

Molecular Weight (Monoisotopic): 414.0958

AlogP: 4.46

#Rotatable Bonds: 5

Polar Surface Area: 78.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.66

CX Basic pKa: ┄

CX LogP: 5.24

CX LogD: 5.05

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -1.35

References

1. Imramovský A, Jorda R, Pauk K, Rezníčková E, Dušek J, Hanusek J, Kryštof V..  (2013)  Substituted 2-hydroxy-N-(arylalkyl)benzamides induce apoptosis in cancer cell lines.,  68  [PMID:23981532] [10.1016/j.ejmech.2013.08.009]

2. Pauk K, Zadražilová I, Imramovský A, Vinšová J, Pokorná M, Masaříková M, Cížek A, Jampílek J..  (2013)  New derivatives of salicylamides: Preparation and antimicrobial activity against various bacterial species.,  21  (21): [PMID:24045008] [10.1016/j.bmc.2013.08.029]

3. Pospisilova S, Michnova H, Kauerova T, Pauk K, Kollar P, Vinsova J, Imramovsky A, Cizek A, Jampilek J..  (2018)  In vitro activity of salicylamide derivatives against vancomycin-resistant enterococci.,  28  (12): [PMID:29773506] [10.1016/j.bmcl.2018.05.011]

Source

Source(1):

• Scientific Literature