(S)-N-(1-(4-bromophenylamino)-3-cyclohexyl-1-oxopropan-2-yl)-5-chloro-2-hydroxybenzamide

ID: ALA2425562

PubChem CID: 72708209

Max Phase: Preclinical

Molecular Formula: C22H24BrClN2O3

Molecular Weight: 479.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](CC1CCCCC1)C(=O)Nc1ccc(Br)cc1)c1cc(Cl)ccc1O

Standard InChI:  InChI=1S/C22H24BrClN2O3/c23-15-6-9-17(10-7-15)25-22(29)19(12-14-4-2-1-3-5-14)26-21(28)18-13-16(24)8-11-20(18)27/h6-11,13-14,19,27H,1-5,12H2,(H,25,29)(H,26,28)/t19-/m0/s1

Standard InChI Key:  GPYSJCXRTFPQPS-IBGZPJMESA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.1270  -23.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1259  -24.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224  -24.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123  -24.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7095  -23.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4206  -22.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009  -24.4711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0041  -22.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2936  -23.2356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0093  -22.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4137  -22.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1229  -23.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291  -22.8190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1260  -24.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5384  -23.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5386  -24.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470  -24.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541  -24.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9484  -23.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394  -22.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8307  -22.8361    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4106  -22.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168  -21.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224  -22.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5265  -21.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5276  -20.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186  -20.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1083  -20.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6639  -24.4417    0.0000 Br  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
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 18 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2425562

   N-[(2S)-1-(4-bromoanilino)-3-cyclohexyl-1-oxopropan-2-yl]-5-chloro-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: 479.80

Molecular Weight (Monoisotopic): 478.0659

AlogP: 5.52

#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: 6.37

CX LogD: 6.18

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -0.85

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