(Z)-4-(3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2-oxoindolin-5-yl)benzaldehyde

ID: ALA3728212

PubChem CID: 118696400

Max Phase: Preclinical

Molecular Formula: C22H18N2O2

Molecular Weight: 342.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c(/C=C2\C(=O)Nc3ccc(-c4ccc(C=O)cc4)cc32)[nH]1

Standard InChI:  InChI=1S/C22H18N2O2/c1-13-9-14(2)23-21(13)11-19-18-10-17(7-8-20(18)24-22(19)26)16-5-3-15(12-25)4-6-16/h3-12,23H,1-2H3,(H,24,26)/b19-11-

Standard InChI Key:  RABWTLKFYXCNBY-ODLFYWEKSA-N

Molfile:  

     RDKit          2D

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   -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
    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
    3.7889    0.0269    0.0000 O   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
   -3.6203    2.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9210    3.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2184    2.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2150    1.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9143    0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5214    3.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5584    3.1303    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  1  0
  8  9  1  0
  9  5  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  2  0
 13 16  1  0
 15 17  1  0
  8 18  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  1 19  1  0
 22 25  1  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3728212

   ---

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: 342.40

Molecular Weight (Monoisotopic): 342.1368

AlogP: 4.60

#Rotatable Bonds: 3

Polar Surface Area: 61.96

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.26

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -0.13

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