US9023865, 5

ID: ALA3703707

PubChem CID: 71555243

Max Phase: Preclinical

Molecular Formula: C21H20N6O

Molecular Weight: 372.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2n[nH]c3cc(NC(=O)NCCc4ccccc4)ncc23)ccn1

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

Standard InChI Key:  SXHJFLZPXBCHPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -1.1395   -7.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4233   -6.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928   -4.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327   -3.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175   -4.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -6.1485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    3.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070    5.2502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078    5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    8.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9171    9.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2187   10.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5151    9.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5099    8.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083    7.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 13 26  2  0
 26 27  1  0
 27 28  2  0
 28  8  1  0
 28 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3703707

   1-[3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-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: 3.69

#Rotatable Bonds: 5

Polar Surface Area: 95.59

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.38

CX Basic pKa: 4.77

CX LogP: 2.76

CX LogD: 2.76

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -1.48

References

1.  (2015)  Compounds that are ERK inhibitors, 

2. Lim J, Kelley EH, Methot JL, Zhou H, Petrocchi A, Chen H, Hill SE, Hinton MC, Hruza A, Jung JO, Maclean JK, Mansueto M, Naumov GN, Philippar U, Raut S, Spacciapoli P, Sun D, Siliphaivanh P..  (2016)  Discovery of 1-(1H-Pyrazolo[4,3-c]pyridin-6-yl)urea Inhibitors of Extracellular Signal-Regulated Kinase (ERK) for the Treatment of Cancers.,  59  (13): [PMID:27329786] [10.1021/acs.jmedchem.6b00708]

Source

Source(2):

• Scientific Literature
• BindingDB Database