N-(3-((1H-indol-3-yl)methylene)-2-oxoindolin-5-yl)-3-(piperidin-1-yl)propanamide

ID: ALA4761972

PubChem CID: 67578679

Max Phase: Preclinical

Molecular Formula: C25H26N4O2

Molecular Weight: 414.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCN1CCCCC1)Nc1ccc2c(c1)/C(=C\c1c[nH]c3ccccc13)C(=O)N2

Standard InChI:  InChI=1S/C25H26N4O2/c30-24(10-13-29-11-4-1-5-12-29)27-18-8-9-23-20(15-18)21(25(31)28-23)14-17-16-26-22-7-3-2-6-19(17)22/h2-3,6-9,14-16,26H,1,4-5,10-13H2,(H,27,30)(H,28,31)/b21-14+

Standard InChI Key:  NSATXVPUIVCJDC-KGENOOAVSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   18.4143  -21.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4131  -22.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1253  -22.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1235  -20.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8363  -21.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8365  -22.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6193  -22.4427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1003  -21.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6189  -21.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7023  -20.9582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9906  -21.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9908  -22.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9216  -21.7758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8711  -20.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3200  -19.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2787  -20.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5669  -21.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8591  -20.9589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1474  -21.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8589  -20.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4355  -20.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1470  -19.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4353  -20.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1685  -19.0580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5013  -19.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7798  -18.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4847  -18.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1939  -18.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1954  -17.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4818  -17.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7795  -17.6919    0.0000 C   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
  1 10  1  0
 10 11  1  0
 11 12  2  0
  8 13  2  0
  9 14  2  0
 14 15  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 19 21  1  0
 20 22  1  0
 21 23  1  0
 23 22  1  0
 15 27  1  0
 26 24  1  0
 24 25  1  0
 25 15  2  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4761972

   N-[(3E)-3-(1H-indol-3-ylmethylidene)-2-oxo-1H-indol-5-yl]-3-piperidin-1-ylpropanamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 414.51

Molecular Weight (Monoisotopic): 414.2056

AlogP: 4.48

#Rotatable Bonds: 5

Polar Surface Area: 77.23

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.41

CX Basic pKa: 9.26

CX LogP: 3.58

CX LogD: 1.72

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: -1.20

References

1. Yao D,Ruhan A,Jiang J,Huang J,Wang J,Han W.  (2020)  Design, synthesis and biological evaluation of 2-indolinone derivatives as PAK1 inhibitors in MDA-MB-231 cells.,  30  (17): [PMID:32738980] [10.1016/j.bmcl.2020.127355]

Source

Source(1):

• Scientific Literature