5-((4-((2-(1H-indol-3-yl)ethyl)amino)-6-chloroquinazolin-2-yl)amino)indolin-2-one

ID: ALA4098355

PubChem CID: 137660199

Max Phase: Preclinical

Molecular Formula: C26H21ClN6O

Molecular Weight: 468.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Cc2cc(Nc3nc(NCCc4c[nH]c5ccccc45)c4cc(Cl)ccc4n3)ccc2N1

Standard InChI:  InChI=1S/C26H21ClN6O/c27-17-5-7-23-20(13-17)25(28-10-9-15-14-29-22-4-2-1-3-19(15)22)33-26(32-23)30-18-6-8-21-16(11-18)12-24(34)31-21/h1-8,11,13-14,29H,9-10,12H2,(H,31,34)(H2,28,30,32,33)

Standard InChI Key:  YRXVIUVOUXJFJE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
    1.8682  -12.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671  -13.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751  -14.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733  -12.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2819  -12.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2827  -13.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9857  -12.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604  -12.3818    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9813  -11.5592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4088  -14.0077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149  -13.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6651   -8.9575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104  -10.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2654   -9.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715   -9.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213  -10.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712  -11.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5632  -11.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8100  -12.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5239  -12.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1302  -12.2241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7909  -11.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9751  -11.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1944  -10.7657    0.0000 O   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
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  1 11  1  0
 10 12  1  0
  8 13  1  0
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 29 17  2  0
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 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 24  1  0
 23 20  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
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098355

   ---

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: 468.95

Molecular Weight (Monoisotopic): 468.1465

AlogP: 5.66

#Rotatable Bonds: 6

Polar Surface Area: 94.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.35

CX Basic pKa: 4.00

CX LogP: 5.43

CX LogD: 5.43

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.26

Np Likeness Score: -1.30

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