N-(2-amino-4-fluorophenyl)-4-(1-phenylcyclopropanecarboxamido)benzamide

ID: ALA4282365

PubChem CID: 145980433

Max Phase: Preclinical

Molecular Formula: C23H20FN3O2

Molecular Weight: 389.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cc(F)ccc1NC(=O)c1ccc(NC(=O)C2(c3ccccc3)CC2)cc1

Standard InChI:  InChI=1S/C23H20FN3O2/c24-17-8-11-20(19(25)14-17)27-21(28)15-6-9-18(10-7-15)26-22(29)23(12-13-23)16-4-2-1-3-5-16/h1-11,14H,12-13,25H2,(H,26,29)(H,27,28)

Standard InChI Key:  SGNVQIGYVYFLHY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    4.2964  -23.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8920  -23.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789  -23.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285  -21.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0273  -22.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7395  -23.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4533  -22.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4505  -21.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7377  -21.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1607  -21.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8741  -21.9231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1577  -20.6918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5803  -21.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2921  -21.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0019  -21.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9992  -20.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2809  -20.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5740  -20.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8632  -20.2883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7090  -20.2721    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.3152  -23.1638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036  -22.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6043  -21.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1841  -22.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895  -21.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4788  -21.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657  -21.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677  -22.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4789  -23.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 18 19  1  0
 16 20  1  0
  5 21  1  0
 21 22  1  0
 22  2  1  0
 22 23  2  0
  2 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4282365

   ---

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: 389.43

Molecular Weight (Monoisotopic): 389.1540

AlogP: 4.33

#Rotatable Bonds: 5

Polar Surface Area: 84.22

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: 2.19

CX LogP: 4.09

CX LogD: 4.09

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.57

Np Likeness Score: -1.42

References

1. Adhikari N, Amin SA, Trivedi P, Jha T, Ghosh B..  (2018)  HDAC3 is a potential validated target for cancer: An overview on the benzamide-based selective HDAC3 inhibitors through comparative SAR/QSAR/QAAR approaches.,  157  [PMID:30179749] [10.1016/j.ejmech.2018.08.081]

Source

Source(1):

• Scientific Literature