3-[2-Chloro-4-(4-fluorphenyl-)benzamido]-4-chloro-N-hydroxybenzamide.

ID: ALA4876103

PubChem CID: 164627964

Max Phase: Preclinical

Molecular Formula: C20H13Cl2FN2O3

Molecular Weight: 419.24

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(Cl)c(NC(=O)c2ccc(-c3ccc(F)cc3)cc2Cl)c1

Standard InChI:  InChI=1S/C20H13Cl2FN2O3/c21-16-8-4-13(19(26)25-28)10-18(16)24-20(27)15-7-3-12(9-17(15)22)11-1-5-14(23)6-2-11/h1-10,28H,(H,24,27)(H,25,26)

Standard InChI Key:  LSQMYZTUXVBHJR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   22.1722   -8.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1710   -9.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8858   -9.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6022   -9.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5993   -8.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8840   -7.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4582   -9.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7437   -9.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0295   -9.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0284  -10.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7476  -10.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4589  -10.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3122   -7.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0281   -8.3154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3091   -7.0807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7410   -7.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4554   -8.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1677   -7.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1651   -7.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4441   -6.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7347   -7.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8836   -8.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8863   -9.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5967   -7.8943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3124   -8.3044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8815   -7.0867    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.0171   -6.6734    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.3142  -10.7990    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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  2  7  1  0
  5 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 18 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
  6 26  1  0
 21 27  1  0
 10 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876103

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 419.24

Molecular Weight (Monoisotopic): 418.0287

AlogP: 5.17

#Rotatable Bonds: 4

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: 9.01

CX Basic pKa: ┄

CX LogP: 4.91

CX LogD: 4.90

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: -1.66

References

1. Ghazy E, Heimburg T, Lancelot J, Zeyen P, Schmidtkunz K, Truhn A, Darwish S, Simoben CV, Shaik TB, Erdmann F, Schmidt M, Robaa D, Romier C, Jung M, Pierce R, Sippl W..  (2021)  Synthesis, structure-activity relationships, cocrystallization and cellular characterization of novel smHDAC8 inhibitors for the treatment of schistosomiasis.,  225  [PMID:34392190] [10.1016/j.ejmech.2021.113745]

Source

Source(1):

• Scientific Literature