N-(4-Ethyl-3-(4-(pyridin-3-yl)-1H-imidazol-2-ylamino)phenyl)benzamide

ID: ALA514458

PubChem CID: 24971210

Max Phase: Preclinical

Molecular Formula: C23H21N5O

Molecular Weight: 383.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(NC(=O)c2ccccc2)cc1Nc1nc(-c2cccnc2)c[nH]1

Standard InChI:  InChI=1S/C23H21N5O/c1-2-16-10-11-19(26-22(29)17-7-4-3-5-8-17)13-20(16)27-23-25-15-21(28-23)18-9-6-12-24-14-18/h3-15H,2H2,1H3,(H,26,29)(H2,25,27,28)

Standard InChI Key:  RVMRDDULSKUOQQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -1.5181    2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5193    1.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8044    1.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0880    1.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909    2.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062    2.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2327    2.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    1.1659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409    1.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0561    1.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3396    2.4046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2341    1.1649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2347    0.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053   -0.1432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509   -0.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -0.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5705   -0.1443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1327   -1.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9541   -1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4393   -2.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1044   -2.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2795   -3.0104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979   -2.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527    0.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7670   -0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4818    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778    1.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630    1.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329    3.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0
  3  4  2  0
  4  8  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
  9 11  2  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
  5  6  2  0
 10 24  2  0
  2 12  1  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 12 13  1  0
 26 27  1  0
 13 14  2  0
 27 28  2  0
 28 10  1  0
  1  2  2  0
  7 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA514458

   N-[4-ethyl-3-[(5-pyridin-3-yl-1H-imidazol-2-yl)amino]phenyl]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: 383.46

Molecular Weight (Monoisotopic): 383.1746

AlogP: 5.03

#Rotatable Bonds: 6

Polar Surface Area: 82.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.14

CX Basic pKa: 7.53

CX LogP: 4.84

CX LogD: 4.49

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -1.45

References

1. Mahboobi S, Sellmer A, Eswayah A, Elz S, Uecker A, Böhmer FD..  (2008)  Inhibition of PDGFR tyrosine kinase activity by a series of novel N-(3-(4-(pyridin-3-yl)-1H-imidazol-2-ylamino)phenyl)amides: a SAR study on the bioisosterism of pyrimidine and imidazole.,  43  (7): [PMID:17983688] [10.1016/j.ejmech.2007.09.021]

Source

Source(1):

• Scientific Literature