N-(4-(5-Amino-1-(4-methoxybenzyl)-1H-pyrazol-4-ylcarbamoyl)-3-methylphenyl)benzo[b]thiophene-2-carboxamide

ID: ALA1684793

PubChem CID: 53318345

Max Phase: Preclinical

Molecular Formula: C24H23N7O3

Molecular Weight: 457.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cn2ncc(NC(=O)c3ccc(NC(=O)c4cnccn4)cc3C)c2N)cc1

Standard InChI:  InChI=1S/C24H23N7O3/c1-15-11-17(29-24(33)21-12-26-9-10-27-21)5-8-19(15)23(32)30-20-13-28-31(22(20)25)14-16-3-6-18(34-2)7-4-16/h3-13H,14,25H2,1-2H3,(H,29,33)(H,30,32)

Standard InChI Key:  YVBRBKKYGXRBBQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   27.3235  -12.9545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7390  -12.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5635  -12.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3295  -11.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4986  -12.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6680  -13.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6660  -14.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3827  -14.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0973  -14.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0959  -13.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3799  -12.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9503  -14.4880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2382  -14.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8076  -12.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5214  -13.2432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5220  -14.0678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3050  -14.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7917  -13.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3075  -12.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5638  -12.2060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6167  -13.6592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0301  -12.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8550  -12.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6186  -12.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2636  -13.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0877  -13.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0861  -12.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2633  -12.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8497  -11.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9722  -12.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7961  -12.9660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2119  -12.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7980  -11.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9755  -11.5348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  2  0
 16 17  2  0
 15 16  1  0
 17 18  1  0
 19 15  1  0
  1  5  1  0
 19 20  1  0
  2  3  1  0
 18 21  1  0
  1  2  1  0
 21 22  1  0
  2  4  2  0
 22 23  1  0
 22 24  2  0
  6  7  2  0
 23 25  2  0
  7  8  1  0
 25 26  1  0
 26  5  2  0
  8  9  2  0
  5 27  1  0
  9 10  1  0
 27 28  2  0
 28 23  1  0
 10 11  2  0
 28 29  1  0
 11  6  1  0
  3 30  2  0
  7 12  1  0
 30 31  1  0
 12 13  1  0
 31 32  2  0
 10 14  1  0
 32 33  1  0
 14 15  1  0
 33 34  2  0
 34  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1684793

   N-[4-[[5-amino-1-[(4-methoxyphenyl)methyl]pyrazol-4-yl]carbamoyl]-3-methylphenyl]pyrazine-2-carboxamide

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: 457.49

Molecular Weight (Monoisotopic): 457.1862

AlogP: 3.13

#Rotatable Bonds: 7

Polar Surface Area: 137.05

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: 2.69

CX LogP: 1.88

CX LogD: 1.88

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.39

Np Likeness Score: -1.91

References

1. Kim MH, Kim M, Yu H, Kim H, Yoo KH, Sim T, Hah JM..  (2011)  Structure based design and syntheses of amino-1H-pyrazole amide derivatives as selective Raf kinase inhibitors in melanoma cells.,  19  (6): [PMID:21353571] [10.1016/j.bmc.2011.01.067]

Source

Source(1):

• Scientific Literature