(R)-5-chloro-N-(1-(4-chlorophenylamino)-1-oxo-3-phenylpropan-2-yl)-2-hydroxybenzamide

ID: ALA2425584

Cas Number: 1227476-98-3

PubChem CID: 46863371

Max Phase: Preclinical

Molecular Formula: C22H18Cl2N2O3

Molecular Weight: 429.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H](Cc1ccccc1)C(=O)Nc1ccc(Cl)cc1)c1cc(Cl)ccc1O

Standard InChI:  InChI=1S/C22H18Cl2N2O3/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/h1-11,13,19,27H,12H2,(H,25,29)(H,26,28)/t19-/m1/s1

Standard InChI Key:  VDXPOMCEKWAGSX-LJQANCHMSA-N

Molfile:  

     RDKit          2D

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   18.4131  -11.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1212  -11.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8308  -11.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8280  -10.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1194  -10.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5392  -11.9160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5342  -10.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2434  -10.6806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5311   -9.4574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9496  -10.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6588  -10.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3650  -10.2640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6619  -11.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0742  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0745  -11.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7829  -11.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4900  -11.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4843  -10.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7753  -10.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9465   -9.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7065  -10.2811    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.6527   -9.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1998  -11.8867    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.3583   -9.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0640   -9.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0614   -8.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3472   -7.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6444   -8.2292    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
  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
 11 21  1  6
  1 22  1  0
 21 23  1  0
 18 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2425584

   5-chloro-N-[(2R)-1-(4-chloroanilino)-1-oxo-3-phenylpropan-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: 429.30

Molecular Weight (Monoisotopic): 428.0694

AlogP: 4.68

#Rotatable Bonds: 6

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: 5.74

CX LogD: 5.55

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.92

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