N2-(2-(1H-indol-3-yl)ethyl)-N4-(1H-indazol-5-yl)quinazoline-2,4-diamine

ID: ALA4098057

PubChem CID: 137659229

Max Phase: Preclinical

Molecular Formula: C25H21N7

Molecular Weight: 419.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc2c(NCCc3c[nH]c4ccccc34)nc(Nc3ccc4[nH]ncc4c3)nc2c1

Standard InChI:  InChI=1S/C25H21N7/c1-3-7-22-19(5-1)16(14-27-22)11-12-26-24-20-6-2-4-8-23(20)30-25(31-24)29-18-9-10-21-17(13-18)15-28-32-21/h1-10,13-15,27H,11-12H2,(H,28,32)(H2,26,29,30,31)

Standard InChI Key:  XCUFKEUWKWBESN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
   16.0164  -13.0255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0152  -13.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7233  -14.2540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7215  -12.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4301  -13.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4308  -13.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1394  -14.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8476  -13.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8429  -13.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1338  -12.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7190  -11.7994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3072  -14.2531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4255  -11.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4231  -10.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1296  -10.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8759  -10.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4209   -9.8771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2114   -9.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0091   -9.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2598   -8.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7137   -7.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9137   -7.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6668   -8.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5998  -13.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6050  -13.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1914  -13.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8985  -14.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1894  -13.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8960  -12.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7266  -11.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9153  -11.7346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5834  -12.4798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  4 11  1  0
  2 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 19  1  0
 18 15  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 12 24  1  0
 24 25  2  0
 25 29  1  0
 28 26  1  0
 26 27  2  0
 27 24  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098057

   ---

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: 419.49

Molecular Weight (Monoisotopic): 419.1858

AlogP: 5.39

#Rotatable Bonds: 6

Polar Surface Area: 94.31

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.77

CX Basic pKa: 4.82

CX LogP: 5.05

CX LogD: 5.04

Aromatic Rings: 6

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -1.44

References

1. Hao C, Huang W, Li X, Guo J, Chen M, Yan Z, Wang K, Jiang X, Song S, Wang J, Zhao D, Li F, Cheng M..  (2017)  Development of 2, 4-diaminoquinazoline derivatives as potent PAK4 inhibitors by the core refinement strategy.,  131  [PMID:28284095] [10.1016/j.ejmech.2017.02.063]

Source

Source(1):

• Scientific Literature