N-Hydroxy-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide

ID: ALA2407730

PubChem CID: 73355098

Max Phase: Preclinical

Molecular Formula: C17H15N5O2

Molecular Weight: 321.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(CNc2nccc(-c3cccnc3)n2)cc1

Standard InChI:  InChI=1S/C17H15N5O2/c23-16(22-24)13-5-3-12(4-6-13)10-20-17-19-9-7-15(21-17)14-2-1-8-18-11-14/h1-9,11,24H,10H2,(H,22,23)(H,19,20,21)

Standard InChI Key:  DMKHBMNHLWJUQI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   14.3451  -14.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3440  -15.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0588  -16.2119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7753  -15.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7725  -14.9679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0570  -14.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6311  -16.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9166  -15.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2022  -16.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2011  -17.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9203  -17.4465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6317  -17.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4904  -16.2098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2043  -15.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9195  -16.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9161  -17.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6304  -17.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3453  -17.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3413  -16.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6264  -15.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0610  -17.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0633  -18.2642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7743  -17.0246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4900  -17.4350    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
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  2  7  1  0
  4 13  1  0
 13 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
 18 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2407730

   N-hydroxy-4-[[(4-pyridin-3-ylpyrimidin-2-yl)amino]methyl]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: 321.34

Molecular Weight (Monoisotopic): 321.1226

AlogP: 2.27

#Rotatable Bonds: 5

Polar Surface Area: 100.03

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.05

CX Basic pKa: 4.34

CX LogP: 1.59

CX LogD: 1.58

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.49

Np Likeness Score: -1.38

References

1. Marson CM, Matthews CJ, Yiannaki E, Atkinson SJ, Soden PE, Shukla L, Lamadema N, Thomas NS..  (2013)  Discovery of potent, isoform-selective inhibitors of histone deacetylase containing chiral heterocyclic capping groups and a N-(2-aminophenyl)benzamide binding unit.,  56  (15): [PMID:23829483] [10.1021/jm400634n]

2. Zhang X, Lv P, Li D, Zhang W, Zhu H.  (2015)  Navigating into the chemical space between MGCD0103 and SAHA: novel histone deacetylase inhibitors as a promising lead,  6  (10): [10.1039/C5MD00247H]

Source

Source(1):

• Scientific Literature