N-(2-aminophenyl)-5-(benzylamino)pyrazine-2-carboxamide

ID: ALA4589724

PubChem CID: 155568230

Max Phase: Preclinical

Molecular Formula: C18H17N5O

Molecular Weight: 319.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ccccc1NC(=O)c1cnc(NCc2ccccc2)cn1

Standard InChI:  InChI=1S/C18H17N5O/c19-14-8-4-5-9-15(14)23-18(24)16-11-22-17(12-20-16)21-10-13-6-2-1-3-7-13/h1-9,11-12H,10,19H2,(H,21,22)(H,23,24)

Standard InChI Key:  VNDKSSOLKIUTSX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   12.3390   -3.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3379   -4.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0459   -4.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7556   -4.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7527   -3.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0441   -3.2189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4589   -3.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1681   -3.6189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4558   -2.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8743   -3.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5820   -3.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2876   -3.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2850   -2.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5708   -1.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8680   -2.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5830   -4.4341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6298   -4.8554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6292   -5.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9211   -6.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2155   -5.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5079   -6.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5068   -6.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2192   -7.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9238   -6.8934    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
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 11 16  1  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4589724

   ---

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: 319.37

Molecular Weight (Monoisotopic): 319.1433

AlogP: 2.92

#Rotatable Bonds: 5

Polar Surface Area: 92.93

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.05

CX LogP: 1.98

CX LogD: 1.98

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -1.46

References

1. Amin SA, Adhikari N, Kotagiri S, Jha T, Ghosh B..  (2019)  Histone deacetylase 3 inhibitors in learning and memory processes with special emphasis on benzamides.,  166  [PMID:30735902] [10.1016/j.ejmech.2019.01.077]

2. Pulya S, Patel T, Paul M, Adhikari N, Banerjee S, Routholla G, Biswas S, Jha T, Ghosh B..  (2022)  Selective inhibition of histone deacetylase 3 by novel hydrazide based small molecules as therapeutic intervention for the treatment of cancer.,  238  [PMID:35635949] [10.1016/j.ejmech.2022.114470]

Source

Source(1):

• Scientific Literature