5-(6-(but-2-en-1-yl)-2-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-2-(morpholine-4-carbonyl)benzonitrile

ID: ALA5268936

Max Phase: Preclinical

Molecular Formula: C24H24N4O3

Molecular Weight: 416.48

Names and Identifiers

Canonical SMILES:  C/C=C/Cn1cc(-c2ccc(C(=O)N3CCOCC3)c(C#N)c2)c2cc(C)[nH]c2c1=O

Standard InChI:  InChI=1S/C24H24N4O3/c1-3-4-7-28-15-21(20-12-16(2)26-22(20)24(28)30)17-5-6-19(18(13-17)14-25)23(29)27-8-10-31-11-9-27/h3-6,12-13,15,26H,7-11H2,1-2H3/b4-3+

Standard InChI Key:  BQAKOVGAYWUDIT-ONEGZZNKSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -0.3340    2.4741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3805    2.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3340    1.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0969   -0.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813   -1.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3306   -0.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353   -0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813   -2.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -2.4738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -2.4738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -3.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0480   -3.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -3.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0480   -2.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8754    1.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3674    2.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8966    2.7247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3805    3.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0487    2.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634    2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780    2.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1927    2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1927    2.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8108   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5255   -1.6485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  7  5  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
  7 12  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 19 18  1  0
 20 19  1  0
 15 20  1  0
  4 21  1  0
 21 22  2  0
 23 22  1  0
  3 23  1  0
  2 24  2  0
  1 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 22 29  1  0
  9 30  1  0
 30 31  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA5268936

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 416.48

Molecular Weight (Monoisotopic): 416.1848

AlogP: 3.23

#Rotatable Bonds: 4

Polar Surface Area: 91.12

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.85

CX Basic pKa: ┄

CX LogP: 2.23

CX LogD: 2.23

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.66

Np Likeness Score: -1.06

References

1. Crawford TD, Vartanian S, Côté A, Bellon S, Duplessis M, Flynn EM, Hewitt M, Huang HR, Kiefer JR, Murray J, Nasveschuk CG, Pardo E, Romero FA, Sandy P, Tang Y, Taylor AM, Tsui V, Wang J, Wang S, Zawadzke L, Albrecht BK, Magnuson SR, Cochran AG, Stokoe D..  (2017)  Inhibition of bromodomain-containing protein 9 for the prevention of epigenetically-defined drug resistance.,  27  (15): [PMID:28606761] [10.1016/j.bmcl.2017.05.063]

Source

Source(1):

• Scientific Literature