4-((4-Benzylpiperazin-1-yl)methyl)-N-hydroxybenzamide

ID: ALA5192796

PubChem CID: 168287377

Max Phase: Preclinical

Molecular Formula: C19H23N3O2

Molecular Weight: 325.41

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(CN2CCN(Cc3ccccc3)CC2)cc1

Standard InChI:  InChI=1S/C19H23N3O2/c23-19(20-24)18-8-6-17(7-9-18)15-22-12-10-21(11-13-22)14-16-4-2-1-3-5-16/h1-9,24H,10-15H2,(H,20,23)

Standard InChI Key:  YUDJFSRXZHYHCF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.5749   -2.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749   -3.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -3.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965   -3.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965   -2.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2881   -2.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358   -2.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358   -1.2357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5760   -0.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5760   -0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358    0.4142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477   -0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477   -0.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358    1.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749    1.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749    2.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2851    2.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0002    2.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0002    1.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2900    1.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7091    2.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7091    3.7023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4218    2.4743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1308    2.8878    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
  1  6  1  0
  1  7  1  0
  7  8  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 11 12  1  0
  8 13  1  0
 13 12  1  0
 11 14  1  0
 14 15  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 18 19  1  0
 15 20  1  0
 20 19  2  0
 18 21  1  0
 21 22  2  0
 21 23  1  0
 24 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5192796

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 325.41

Molecular Weight (Monoisotopic): 325.1790

AlogP: 2.12

#Rotatable Bonds: 5

Polar Surface Area: 55.81

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.07

CX Basic pKa: 7.75

CX LogP: 2.10

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: -0.88

References

1. Hashimoto K, Ide S, Arata M, Nakata A, Ito A, Ito TK, Kudo N, Lin B, Nunomura K, Tsuganezawa K, Yoshida M, Nagaoka Y, Sumiyoshi T..  (2022)  Discovery of Benzylpiperazine Derivatives as CNS-Penetrant and Selective Histone Deacetylase 6 Inhibitors.,  13  (7.0): [PMID:35859864] [10.1021/acsmedchemlett.2c00081]

Source

Source(1):

• Scientific Literature