4-((2-(tert-Butyl)-1H-indol-1-yl)methyl)-N-hydroxybenzamide

ID: ALA4468860

PubChem CID: 155533398

Max Phase: Preclinical

Molecular Formula: C20H22N2O2

Molecular Weight: 322.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc2ccccc2n1Cc1ccc(C(=O)NO)cc1

Standard InChI:  InChI=1S/C20H22N2O2/c1-20(2,3)18-12-16-6-4-5-7-17(16)22(18)13-14-8-10-15(11-9-14)19(23)21-24/h4-12,24H,13H2,1-3H3,(H,21,23)

Standard InChI Key:  YTLCVCCFNDIFMM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   18.0676   -5.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0664   -5.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7745   -6.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4842   -5.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4813   -5.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7727   -4.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1925   -6.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1938   -7.1408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8996   -5.9139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6079   -6.3214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3598   -4.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3596   -3.8715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7673   -2.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0185   -3.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6979   -3.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9510   -2.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4084   -2.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6126   -2.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3622   -2.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9065   -3.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7962   -3.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9675   -4.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4025   -3.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5837   -3.8466    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
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  1 11  1  0
 11 12  1  0
 12 14  1  0
 13 16  1  0
 15 12  1  0
 13 14  2  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
 14 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4468860

   ---

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: 322.41

Molecular Weight (Monoisotopic): 322.1681

AlogP: 4.11

#Rotatable Bonds: 3

Polar Surface Area: 54.26

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 4.33

CX LogD: 4.33

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.56

Np Likeness Score: -0.97

References

1. Géraldy M, Morgen M, Sehr P, Steimbach RR, Moi D, Ridinger J, Oehme I, Witt O, Malz M, Nogueira MS, Koch O, Gunkel N, Miller AK..  (2019)  Selective Inhibition of Histone Deacetylase 10: Hydrogen Bonding to the Gatekeeper Residue is Implicated.,  62  (9): [PMID:30964290] [10.1021/acs.jmedchem.8b01936]

Source

Source(1):

• Scientific Literature