N-Hydroxy-4-(3-methyl-2-phenyl-butyrylamino)-benzamide

ID: ALA191091

PubChem CID: 6918801

Max Phase: Preclinical

Molecular Formula: C18H20N2O3

Molecular Weight: 312.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C(C(=O)Nc1ccc(C(=O)NO)cc1)c1ccccc1

Standard InChI:  InChI=1S/C18H20N2O3/c1-12(2)16(13-6-4-3-5-7-13)18(22)19-15-10-8-14(9-11-15)17(21)20-23/h3-12,16,23H,1-2H3,(H,19,22)(H,20,21)

Standard InChI Key:  LAMIXXKAWNLXOC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.0042   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -1.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750    0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -0.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750    1.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -0.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417    0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042    0.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333    0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  1  1  0
  5  1  2  0
  6 11  1  0
  7  3  2  0
  8  3  1  0
  9  4  1  0
 10  2  1  0
 11 15  2  0
 12 14  1  0
 13  4  1  0
 14 10  2  0
 15 10  1  0
 16  8  1  0
 17  9  1  0
 18  9  2  0
 19 13  1  0
 20 13  1  0
 21 17  2  0
 22 18  1  0
 23 22  2  0
  6 12  2  0
 23 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA191091

   N-hydroxy-4-[(3-methyl-2-phenylbutanoyl)amino]benzamide

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: 312.37

Molecular Weight (Monoisotopic): 312.1474

AlogP: 3.18

#Rotatable Bonds: 5

Polar Surface Area: 78.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 3.16

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: -0.94

References

1. Lu Q, Wang DS, Chen CS, Hu YD, Chen CS..  (2005)  Structure-based optimization of phenylbutyrate-derived histone deacetylase inhibitors.,  48  (17): [PMID:16107152] [10.1021/jm0503749]

2. PubChem BioAssay data set, 

3. Tng J, Lim J, Wu KC, Lucke AJ, Xu W, Reid RC, Fairlie DP..  (2020)  Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class I HDAC Enzymes and Cancer Cell Proliferation.,  63  (11): [PMID:32383881] [10.1021/acs.jmedchem.0c00230]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays