3-[N-(4-Chlorobenzyl)amino]-4-methylbenzhydroxamic acid

ID: ALA4097353

PubChem CID: 137662006

Max Phase: Preclinical

Molecular Formula: C15H15ClN2O2

Molecular Weight: 290.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)NO)cc1NCc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C15H15ClN2O2/c1-10-2-5-12(15(19)18-20)8-14(10)17-9-11-3-6-13(16)7-4-11/h2-8,17,20H,9H2,1H3,(H,18,19)

Standard InChI Key:  QJSJFQHMDUHUEW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   16.2929  -19.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2917  -20.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9998  -21.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7094  -20.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7066  -19.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9980  -19.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5837  -21.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4178  -21.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4191  -21.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1249  -20.7018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8332  -21.1093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5851  -19.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8763  -20.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1683  -21.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4617  -20.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7541  -21.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7530  -21.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4654  -22.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1700  -21.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0455  -22.3345    0.0000 Cl  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
  2  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  1 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097353

   ---

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: 290.75

Molecular Weight (Monoisotopic): 290.0822

AlogP: 3.38

#Rotatable Bonds: 4

Polar Surface Area: 61.36

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: 3.03

CX LogP: 3.14

CX LogD: 3.13

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.60

Np Likeness Score: -1.57

References

1. Heimburg T, Kolbinger FR, Zeyen P, Ghazy E, Herp D, Schmidtkunz K, Melesina J, Shaik TB, Erdmann F, Schmidt M, Romier C, Robaa D, Witt O, Oehme I, Jung M, Sippl W..  (2017)  Structure-Based Design and Biological Characterization of Selective Histone Deacetylase 8 (HDAC8) Inhibitors with Anti-Neuroblastoma Activity.,  60  (24): [PMID:29190092] [10.1021/acs.jmedchem.7b01447]

Source

Source(1):

• Scientific Literature