(3Z)-N-(4-(methylsulfonyl)phenyl)-N'-(2-oxo-3-(thiophen-2-ylmethylene)indolin-5-yl)urea

ID: ALA3735845

PubChem CID: 127037284

Max Phase: Preclinical

Molecular Formula: C21H17N3O4S2

Molecular Weight: 439.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1ccc(NC(=O)Nc2ccc3c(c2)/C(=C/c2cccs2)C(=O)N3)cc1

Standard InChI:  InChI=1S/C21H17N3O4S2/c1-30(27,28)16-7-4-13(5-8-16)22-21(26)23-14-6-9-19-17(11-14)18(20(25)24-19)12-15-3-2-10-29-15/h2-12H,1H3,(H,24,25)(H2,22,23,26)/b18-12-

Standard InChI Key:  MMVHFHCKSSPWQC-PDGQHHTCSA-N

Molfile:  

     RDKit          2D

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    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
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    4.2542   -4.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7448   -4.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0456   -2.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7409   -1.9129    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
   -4.9530   -9.7386    0.0000 S   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
   -3.9156  -10.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9938  -10.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9564  -10.9386    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
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  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
  7 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 20 26  1  0
 18 27  2  0
 24 28  1  0
 24 29  2  0
 24 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3735845

   ---

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: 439.52

Molecular Weight (Monoisotopic): 439.0660

AlogP: 4.29

#Rotatable Bonds: 4

Polar Surface Area: 104.37

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.93

CX Basic pKa: ┄

CX LogP: 3.16

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.53

Np Likeness Score: -1.77

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