1-[7-(1-Methyl-1H-pyrazol-4-yl)-1,5-naphthyridin-2-yl]-3-(2-phenylethyl)urea

ID: ALA3318030

PubChem CID: 53239587

Max Phase: Preclinical

Molecular Formula: C21H20N6O

Molecular Weight: 372.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2cnc3ccc(NC(=O)NCCc4ccccc4)nc3c2)cn1

Standard InChI:  InChI=1S/C21H20N6O/c1-27-14-17(13-24-27)16-11-19-18(23-12-16)7-8-20(25-19)26-21(28)22-10-9-15-5-3-2-4-6-15/h2-8,11-14H,9-10H2,1H3,(H2,22,25,26,28)

Standard InChI Key:  AEBGAQZHEWUQER-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    8.5669   -4.3336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8578   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6860   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2719   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1041   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5182   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3950   -4.3336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1041   -3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9810   -4.3336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5182   -3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8132   -2.6992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6860   -3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8132   -4.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2719   -3.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3950   -2.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2273   -4.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3134   -5.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1141   -5.3161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5227   -4.6069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9745   -3.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4471   -6.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1505   -4.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1548   -5.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4535   -5.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4574   -6.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1626   -6.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8651   -6.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8577   -5.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 16  1  0
  3 12  1  0
  7  5  1  0
 12 15  2  0
  4 14  2  0
 15  8  1  0
 10  6  2  0
 11 10  1  0
  7  3  2  0
 13  5  2  0
  8 11  2  0
  9  3  1  0
  4  9  1  0
  1  4  1  0
  1  2  1  0
  6 13  1  0
  8  5  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
 18 21  1  0
  2 22  1  0
 23 22  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3318030

   1-[7-(1-Methylpyrazol-4-yl)-1,5-naphthyridin-2-yl]-3-(2-phenylethyl)urea

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: 372.43

Molecular Weight (Monoisotopic): 372.1699

AlogP: 3.39

#Rotatable Bonds: 5

Polar Surface Area: 84.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.78

CX Basic pKa: 2.57

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -2.00

References

1. Defaux J, Antoine M, Logé C, Le Borgne M, Schuster T, Seipelt I, Aicher B, Teifel M, Günther E, Gerlach M, Marchand P..  (2014)  Discovery of (7-aryl-1,5-naphthyridin-2-yl)ureas as dual inhibitors of ERK2 and Aurora B kinases with antiproliferative activity against cancer cells.,  24  (16): [PMID:25022204] [10.1016/j.bmcl.2014.06.078]

Source

Source(1):

• Scientific Literature