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

ID: ALA473322

PubChem CID: 24971111

Max Phase: Preclinical

Molecular Formula: C23H21N5O

Molecular Weight: 383.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C(=O)Nc2ccc(C)c(Nc3nc(-c4cccnc4)c[nH]3)c2)c1

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

Standard InChI Key:  ARYPTQHOZWFSFI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.5681  -11.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693  -12.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8544  -12.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1380  -12.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1409  -11.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562  -11.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2827  -11.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771  -12.6966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2909  -12.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061  -12.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2896  -11.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2841  -12.6976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847  -13.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9553  -14.0057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009  -14.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8759  -14.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205  -14.0068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1827  -15.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041  -15.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4893  -16.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1544  -16.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295  -16.8729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8479  -16.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027  -13.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7170  -13.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318  -13.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4278  -12.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7130  -12.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1402  -12.2700    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
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA473322

   3-methyl-N-[4-methyl-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: 5.08

#Rotatable Bonds: 5

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: 4.91

CX LogD: 4.56

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -1.78

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