N-((cis)-3-azabicyclo[3.1.0]hexan-6-yl)-2,4-dimethyl-5-((Z)-(2-oxo-5-(1-phenyl-1H-pyrazol-4-yl)indolin-3-ylidene)methyl)-1H-pyrrole-3-carboxamide dihydrochloride

ID: ALA3732058

PubChem CID: 127036536

Max Phase: Preclinical

Molecular Formula: C30H30Cl2N6O2

Molecular Weight: 504.59

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)N[C@H]1[C@@H]2CNC[C@@H]21.Cl.Cl

Standard InChI:  InChI=1S/C30H28N6O2.2ClH/c1-16-26(33-17(2)27(16)30(38)35-28-23-13-31-14-24(23)28)11-22-21-10-18(8-9-25(21)34-29(22)37)19-12-32-36(15-19)20-6-4-3-5-7-20;;/h3-12,15,23-24,28,31,33H,13-14H2,1-2H3,(H,34,37)(H,35,38);2*1H/b22-11-;;/t23-,24+,28+;;

Standard InChI Key:  SISYAXFBGUBROU-OBUWGQEBSA-N

Molfile:  

     RDKit          2D

 42 46  0  0  0  0  0  0  0  0999 V2000
   13.9821    3.4164    0.0000 Cl  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
    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
    4.2449    4.2986    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
    6.0412    2.6666    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
   -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
    3.6433    5.3370    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
    6.7457    5.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3820    6.3856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2119    4.9213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2234    6.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8246    7.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5599    5.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4821    6.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0653    8.0761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7468    8.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8012    7.1070    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2464    6.7088    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4821    3.4164    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
  9 11  2  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
  2 18  1  0
 20 23  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
 14 29  1  0
 16 30  1  0
 15 31  1  0
 31 32  2  0
 31 33  1  0
 34 33  1  6
 36 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 35  1  0
 35 40  1  6
 36 41  1  6
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: 504.59

Molecular Weight (Monoisotopic): 504.2274

AlogP: 3.92

#Rotatable Bonds: 5

Polar Surface Area: 103.84

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.33

CX Basic pKa: 10.66

CX LogP: 2.61

CX LogD: 0.02

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.31

Np Likeness Score: -0.87

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