3-(2,4-Dichlorobenzyloxy)-4-methoxybenzhydroxamic acid

ID: ALA4095909

PubChem CID: 137652925

Max Phase: Preclinical

Molecular Formula: C15H13Cl2NO4

Molecular Weight: 342.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)NO)cc1OCc1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C15H13Cl2NO4/c1-21-13-5-3-9(15(19)18-20)6-14(13)22-8-10-2-4-11(16)7-12(10)17/h2-7,20H,8H2,1H3,(H,18,19)

Standard InChI Key:  MABBOOSTBYKIJW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    7.0066  -17.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0055  -18.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7135  -19.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4232  -18.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4203  -17.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7117  -17.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2974  -19.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1315  -19.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1328  -19.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8386  -18.5928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5469  -19.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2988  -17.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5912  -17.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5901  -18.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8820  -19.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1754  -18.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4678  -18.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4668  -19.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791  -20.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8838  -19.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5925  -20.2225    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7593  -20.2254    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
 12 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 20 21  1  0
 18 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095909

   ---

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: 342.18

Molecular Weight (Monoisotopic): 341.0222

AlogP: 3.70

#Rotatable Bonds: 5

Polar Surface Area: 67.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 3.43

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: -1.10

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