3-(4-Acetyl-2-ethoxy-phenylcarbamoyl)-N-hydroxy-4-methoxybenzamide

ID: ALA4878820

PubChem CID: 164626073

Max Phase: Preclinical

Molecular Formula: C19H20N2O6

Molecular Weight: 372.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1ccc(C(C)=O)cc1NC(=O)c1cc(C(=O)NO)ccc1OC

Standard InChI:  InChI=1S/C19H20N2O6/c1-4-27-17-8-5-12(11(2)22)10-15(17)20-19(24)14-9-13(18(23)21-25)6-7-16(14)26-3/h5-10,25H,4H2,1-3H3,(H,20,24)(H,21,23)

Standard InChI Key:  QHYDZMMXOLOKOS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.7319   -3.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307   -4.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455   -4.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1619   -4.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1591   -3.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4437   -3.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8720   -3.0310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5880   -3.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3009   -3.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0154   -3.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7277   -3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7251   -2.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0040   -1.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2945   -2.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4436   -3.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4463   -4.2596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1566   -3.0197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8725   -3.4299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5911   -4.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5770   -1.7988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5706   -0.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412   -2.2121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -1.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7231   -0.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4453   -5.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1597   -5.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307   -5.9275    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
 20 21  1  0
  6 22  1  0
 22 23  1  0
 23 24  1  0
  3 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878820

   ---

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: 372.38

Molecular Weight (Monoisotopic): 372.1321

AlogP: 2.67

#Rotatable Bonds: 7

Polar Surface Area: 113.96

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 1.51

CX LogD: 1.50

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: -1.10

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