(3E)-N-(4-(methylthio)phenyl)-N'-(2-oxo-(3-(1-methyl-1H-imidazol-2-yl)methylene)-indolin-5-yl)urea

ID: ALA3736265

PubChem CID: 127037283

Max Phase: Preclinical

Molecular Formula: C21H19N5O2S

Molecular Weight: 405.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ccc(NC(=O)Nc2ccc3c(c2)/C(=C\c2nccn2C)C(=O)N3)cc1

Standard InChI:  InChI=1S/C21H19N5O2S/c1-26-10-9-22-19(26)12-17-16-11-14(5-8-18(16)25-20(17)27)24-21(28)23-13-3-6-15(29-2)7-4-13/h3-12H,1-2H3,(H,25,27)(H2,23,24,28)/b17-12+

Standard InChI Key:  HHVUJHPMRXIBKN-SFQUDFHCSA-N

Molfile:  

     RDKit          2D

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    3.7889    0.0269    0.0000 O   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 N   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
   -1.0028    1.5132    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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1889   -3.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2891   -3.5814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927   -4.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -5.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5222   -5.1969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6236   -5.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187   -1.4919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267   -2.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300   -3.7369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9380   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2396   -5.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2445   -7.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480   -8.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9499   -9.7387    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118  -10.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6465   -7.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415   -5.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5905   -3.5979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  4  9  1  0
  9 10  1  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 12 16  1  0
 16 17  1  0
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 21 28  1  0
 19 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3736265

   ---

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: 405.48

Molecular Weight (Monoisotopic): 405.1259

AlogP: 4.28

#Rotatable Bonds: 4

Polar Surface Area: 88.05

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.11

CX Basic pKa: 5.96

CX LogP: 3.37

CX LogD: 3.36

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -1.46

References

1. Sestito S, Nesi G, Daniele S, Martelli A, Digiacomo M, Borghini A, Pietra D, Calderone V, Lapucci A, Falasca M, Parrella P, Notarangelo A, Breschi MC, Macchia M, Martini C, Rapposelli S..  (2015)  Design and synthesis of 2-oxindole based multi-targeted inhibitors of PDK1/Akt signaling pathway for the treatment of glioblastoma multiforme.,  105  [PMID:26498573] [10.1016/j.ejmech.2015.10.020]

Source

Source(1):

• Scientific Literature