N-hydroxy-3-(4-isopropoxybenzamido)-4-methoxybenzamide

ID: ALA4869825

PubChem CID: 164624269

Max Phase: Preclinical

Molecular Formula: C18H20N2O5

Molecular Weight: 344.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)NO)cc1NC(=O)c1ccc(OC(C)C)cc1

Standard InChI:  InChI=1S/C18H20N2O5/c1-11(2)25-14-7-4-12(5-8-14)17(21)19-15-10-13(18(22)20-23)6-9-16(15)24-3/h4-11,23H,1-3H3,(H,19,21)(H,20,22)

Standard InChI Key:  XCRRMDGVURVBFB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   14.6857  -21.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6845  -22.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3993  -22.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1157  -22.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1128  -21.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3975  -21.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8258  -21.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5417  -21.7028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8226  -20.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2547  -21.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9690  -21.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6814  -21.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6788  -20.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9578  -20.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2483  -20.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3973  -21.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3999  -22.5215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1103  -21.2817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8262  -21.6918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9697  -22.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2556  -22.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5307  -20.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5244  -19.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2562  -21.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5408  -22.9500    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
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 12 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 15 22  1  0
 22 23  1  0
 21 24  1  0
 21 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4869825

   ---

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: 344.37

Molecular Weight (Monoisotopic): 344.1372

AlogP: 2.85

#Rotatable Bonds: 6

Polar Surface Area: 96.89

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: 2.36

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.55

Np Likeness Score: -1.17

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