5-(3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-2-oxoindolin-1-yl)-1,3,3-trimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

ID: ALA4215413

PubChem CID: 129104273

Max Phase: Preclinical

Molecular Formula: C25H25N5O2

Molecular Weight: 427.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncc(-c2ccc3c(c2)N(c2cnc4c(c2)C(C)(C)C(=O)N4C)C(=O)C3(C)C)cn1

Standard InChI:  InChI=1S/C25H25N5O2/c1-14-26-11-16(12-27-14)15-7-8-18-20(9-15)30(23(32)24(18,2)3)17-10-19-21(28-13-17)29(6)22(31)25(19,4)5/h7-13H,1-6H3

Standard InChI Key:  LPQZXFAKLZIAFI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   26.2739  -14.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6961  -14.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4890  -15.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4043  -10.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4084  -10.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1141  -10.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2155  -11.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2143  -12.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9224  -12.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9206  -10.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5082  -12.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8005  -12.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0930  -12.4421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0919  -13.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8042  -13.6692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5089  -13.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6292  -11.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6340  -12.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4184  -12.2872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8984  -11.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7156  -11.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4033  -13.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6866  -13.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6712  -14.3157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3844  -13.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1012  -13.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0910  -14.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3744  -14.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5393  -15.5484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3578  -15.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9876  -16.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7618  -16.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  2  0
  8  9  1  0
  9 18  2  0
 17 10  2  0
 10  7  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  8 11  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  5  1  0
  5 17  1  0
 20 21  2  0
 22 23  2  0
 23 24  1  0
 24 28  2  0
 26 22  1  0
 19 22  1  0
 14 25  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30  2  1  0
  2 27  1  0
 29 31  1  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4215413

   ---

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: 427.51

Molecular Weight (Monoisotopic): 427.2008

AlogP: 4.06

#Rotatable Bonds: 2

Polar Surface Area: 79.29

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.27

CX LogP: 3.53

CX LogD: 3.53

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.62

Np Likeness Score: -0.51

References

1. Rosse G..  (2017)  Indolinone Inhibitors of ENT1 for the Treatment of Schizophrenia.,  8  (10): [PMID:29057039] [10.1021/acsmedchemlett.7b00378]

Source

Source(1):

• Scientific Literature