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

ID: ALA3727926

PubChem CID: 117622390

Max Phase: Preclinical

Molecular Formula: C32H36N6O2

Molecular Weight: 536.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCCNC(=O)c1c(C)[nH]c(/C=C2\C(=O)Nc3ccc(-c4cnn(-c5ccccc5)c4)cc32)c1C

Standard InChI:  InChI=1S/C32H36N6O2/c1-5-37(6-2)16-10-15-33-32(40)30-21(3)29(35-22(30)4)18-27-26-17-23(13-14-28(26)36-31(27)39)24-19-34-38(20-24)25-11-8-7-9-12-25/h7-9,11-14,17-20,35H,5-6,10,15-16H2,1-4H3,(H,33,40)(H,36,39)/b27-18-

Standard InChI Key:  NRMVNOHALPEPOV-IMRQLAEWSA-N

Molfile:  

     RDKit          2D

 40 44  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
   -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 C   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
    7.8361   10.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3766   11.7583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3835   12.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9101   12.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5440   13.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0162   14.0136    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
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 24  1  0
  1 24  1  0
 26 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 23 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 37 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3727926

   N-[3-(diethylamino)propyl]-2,4-dimethyl-5-[(Z)-[2-oxo-5-(1-phenylpyrazol-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: 536.68

Molecular Weight (Monoisotopic): 536.2900

AlogP: 5.44

#Rotatable Bonds: 10

Polar Surface Area: 95.05

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.19

CX Basic pKa: 9.82

CX LogP: 4.34

CX LogD: 2.17

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.19

Np Likeness Score: -1.30

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