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

ID: ALA3730037

PubChem CID: 127036534

Max Phase: Preclinical

Molecular Formula: C31H34Cl2N6O2

Molecular Weight: 520.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1[nH]c(/C=C2\C(=O)Nc3ccc(-c4cnn(-c5ccccc5)c4)cc32)c(C)c1C(=O)NCC1(N)CCCC1.Cl.Cl

Standard InChI:  InChI=1S/C31H32N6O2.2ClH/c1-19-27(35-20(2)28(19)30(39)33-18-31(32)12-6-7-13-31)15-25-24-14-21(10-11-26(24)36-29(25)38)22-16-34-37(17-22)23-8-4-3-5-9-23;;/h3-5,8-11,14-17,35H,6-7,12-13,18,32H2,1-2H3,(H,33,39)(H,36,38);2*1H/b25-15-;;

Standard InChI Key:  MVWAOHYYFDIZPA-JWLSWTATSA-N

Molfile:  

     RDKit          2D

 41 44  0  0  0  0  0  0  0  0999 V2000
   10.7082    4.5310    0.0000 Cl  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
    5.7737    8.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4769    8.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7929   10.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2852   10.5753    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
   -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
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    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
    7.6345   10.1062    0.0000 N   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
   13.2082    4.5310    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 14 16  2  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  2  0
 20 23  1  0
 22 24  1  0
 21 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28  2  1  0
  2 29  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 30  1  0
  7 30  1  0
 32 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 35  1  0
M  END

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: 520.64

Molecular Weight (Monoisotopic): 520.2587

AlogP: 4.98

#Rotatable Bonds: 6

Polar Surface Area: 117.83

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.19

CX Basic pKa: 9.70

CX LogP: 4.06

CX LogD: 2.03

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.27

Np Likeness Score: -0.92

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