3-(4-Acetyl-2-methoxy-phenylcarbamoyl)-4-chloro-N-hydroxybenzamide

ID: ALA4866890

PubChem CID: 164624154

Max Phase: Preclinical

Molecular Formula: C17H15ClN2O5

Molecular Weight: 362.77

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(C(C)=O)cc1NC(=O)c1cc(C(=O)NO)ccc1Cl

Standard InChI:  InChI=1S/C17H15ClN2O5/c1-9(21)10-4-6-15(25-2)14(8-10)19-17(23)12-7-11(16(22)20-24)3-5-13(12)18/h3-8,24H,1-2H3,(H,19,23)(H,20,22)

Standard InChI Key:  RHPDEYIVLYNXPS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   14.7858   -2.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7847   -3.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4995   -4.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2159   -3.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2130   -2.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4977   -2.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9260   -2.5353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6420   -2.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3549   -2.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0693   -2.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7817   -2.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7790   -1.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0580   -1.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3486   -1.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4975   -2.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5002   -3.7638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2106   -2.5240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9264   -2.9340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6450   -3.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6309   -1.3030    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.4952   -1.7163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7795   -1.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4993   -5.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2136   -5.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7847   -5.4317    0.0000 O   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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  8 19  2  0
 14 20  1  0
  6 21  1  0
 21 22  1  0
  3 23  1  0
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4866890

   ---

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: 362.77

Molecular Weight (Monoisotopic): 362.0669

AlogP: 2.92

#Rotatable Bonds: 5

Polar Surface Area: 104.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.01

CX Basic pKa: ┄

CX LogP: 1.92

CX LogD: 1.91

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: -1.24

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