(S)-5-chloro-N-(3-cyclohexyl-1-oxo-1-(3-(trifluoromethyl)phenylamino)propan-2-yl)-2-hydroxybenzamide

ID: ALA2425561

PubChem CID: 72708208

Max Phase: Preclinical

Molecular Formula: C23H24ClF3N2O3

Molecular Weight: 468.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](CC1CCCCC1)C(=O)Nc1cccc(C(F)(F)F)c1)c1cc(Cl)ccc1O

Standard InChI:  InChI=1S/C23H24ClF3N2O3/c24-16-9-10-20(30)18(13-16)21(31)29-19(11-14-5-2-1-3-6-14)22(32)28-17-8-4-7-15(12-17)23(25,26)27/h4,7-10,12-14,19,30H,1-3,5-6,11H2,(H,28,32)(H,29,31)/t19-/m0/s1

Standard InChI Key:  GEDNWCDPRLAKEC-IBGZPJMESA-N

Molfile:  

     RDKit          2D

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   27.9470  -19.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6551  -20.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3647  -19.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.0731  -20.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0681  -18.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7773  -18.8029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0650  -17.5798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4835  -18.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1927  -18.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8989  -18.3863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1958  -19.6148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6081  -18.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6083  -19.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.3092  -18.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2404  -18.4034    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   31.4804  -17.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1866  -17.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7229  -18.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4336  -18.7723    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.7169  -17.5517    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.4269  -17.9534    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.8922  -17.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5963  -17.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5974  -16.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8883  -15.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1781  -16.3485    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
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  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
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 12 14  2  0
 13 15  1  0
 15 16  2  0
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 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
 19 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 23 28  1  0
 23 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2425561

   5-chloro-N-[(2S)-3-cyclohexyl-1-oxo-1-[3-(trifluoromethyl)anilino]propan-2-yl]-2-hydroxybenzamide

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: 468.90

Molecular Weight (Monoisotopic): 468.1428

AlogP: 5.77

#Rotatable Bonds: 6

Polar Surface Area: 78.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.66

CX Basic pKa: ┄

CX LogP: 6.48

CX LogD: 6.29

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -1.08

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]

Source

Source(1):

• Scientific Literature