4-(5-(2-nitroso-2,3-dihydro-5H-inden-5-ylidene)-2-(piperidin-4-yl)-3,5-dihydro-4H-imidazol-4-ylidene)-1,4-dihydropyridine

ID: ALA5288660

Max Phase: Preclinical

Molecular Formula: C22H23N5O

Molecular Weight: 373.46

Names and Identifiers

Canonical SMILES:  O=NC1C=c2cc/c(=c3\nc(C4CCNCC4)[nH]c3=C3C=CNC=C3)cc2C1

Standard InChI:  InChI=1S/C22H23N5O/c28-27-19-12-16-1-2-17(11-18(16)13-19)21-20(14-3-7-23-8-4-14)25-22(26-21)15-5-9-24-10-6-15/h1-4,7-8,11-12,15,19,23-24H,5-6,9-10,13H2,(H,25,26)/b21-17+

Standard InChI Key:  BYFHOKFVPQCBBK-HEHNFIMWSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   -0.3060   -2.0945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9735   -1.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7186   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -1.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705   -1.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9840   -2.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7811   -2.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646   -2.2503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509   -1.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3540   -1.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1583   -1.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7418   -1.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5388   -1.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7524   -2.2504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689   -2.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718   -2.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -0.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064    0.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190    1.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3441    1.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7567    0.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3441   -0.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5637    0.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8962    1.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500    1.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3646    2.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3646    2.8339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  2  1  0
  6  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
  6 11  1  0
 11 10  1  0
 12  5  2  0
 12 13  1  0
 14 13  2  0
 15 14  1  0
 16 15  1  0
 12 17  1  0
 17 16  2  0
 18  4  2  0
 18 19  1  0
 20 19  2  0
 21 20  1  0
 22 21  1  0
 18 23  1  0
 23 22  2  0
 22 24  1  0
 21 25  2  0
 25 26  1  0
 26 24  1  0
 26 27  1  0
 27 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5288660

   ---

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: 373.46

Molecular Weight (Monoisotopic): 373.1903

AlogP: 1.42

#Rotatable Bonds: 2

Polar Surface Area: 82.17

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.24

CX Basic pKa: 10.44

CX LogP: -0.92

CX LogD: -4.29

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.70

Np Likeness Score: 0.29

References

1. Carlino L, Rastelli G..  (2016)  Dual Kinase-Bromodomain Inhibitors in Anticancer Drug Discovery: A Structural and Pharmacological Perspective.,  59  (20): [PMID:27559828] [10.1021/acs.jmedchem.6b00438]

Source

Source(1):

• Scientific Literature