(Z)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-5-((2-oxo-5-(1-(pyridin-3-yl)-1H-pyrazol-4-yl)indolin-3-ylidene)methyl)-1H-pyrrole-3-carboxamide

ID: ALA3732483

PubChem CID: 117622453

Max Phase: Preclinical

Molecular Formula: C30H33N7O2

Molecular Weight: 523.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCNC(=O)c1c(C)[nH]c(/C=C2\C(=O)Nc3ccc(-c4cnn(-c5cccnc5)c4)cc32)c1C

Standard InChI:  InChI=1S/C30H33N7O2/c1-5-36(6-2)13-12-32-30(39)28-19(3)27(34-20(28)4)15-25-24-14-21(9-10-26(24)35-29(25)38)22-16-33-37(18-22)23-8-7-11-31-17-23/h7-11,14-18,34H,5-6,12-13H2,1-4H3,(H,32,39)(H,35,38)/b25-15-

Standard InChI Key:  VLJPCUOBYKWXOK-MYYYXRDXSA-N

Molfile:  

     RDKit          2D

 39 43  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7388    1.9224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0412    2.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7359    4.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    4.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1353    2.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433    5.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7411    5.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9142    4.9935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2817    6.6750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2886    7.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8291    9.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8361   10.3296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3766   11.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3039   10.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1080   10.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1817   12.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168    1.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580    2.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2259    3.2843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9730    1.9836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669    0.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8393    4.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0560    5.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7704    7.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2699    7.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0549    6.0091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3406    4.6901    0.0000 C   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  1  0
  8  9  1  0
  9  5  1  0
  8 10  2  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  2  0
 14 17  1  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 25 28  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 29  1  0
  1 29  1  0
 31 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3732483

   N-[2-(diethylamino)ethyl]-2,4-dimethyl-5-[(Z)-[2-oxo-5-(1-pyridin-3-ylpyrazol-4-yl)-1H-indol-3-ylidene]methyl]-1H-pyrrole-3-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: 523.64

Molecular Weight (Monoisotopic): 523.2696

AlogP: 4.44

#Rotatable Bonds: 9

Polar Surface Area: 107.94

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.18

CX Basic pKa: 9.04

CX LogP: 3.30

CX LogD: 1.65

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.28

Np Likeness Score: -1.38

References

1.  (2014)  3-(aryl or heteroaryl) methyleneindolin-2-one derivatives as inhibitors of cancer stem cell pathway kinases for the treatment of cancer, 

2.  (2019)  3-(aryl or heteroaryl) methyleneindolin-2-one derivatives as inhibitors of cancer stem cell pathway kinases for the treatment of cancer, 

Source

Source(1):

• Patent Bioactivity Data