(2Z,3E)-3-(((1-Methylpiperidin-4-yl)oxy)imino)-[2,3'-biindolinylidene]-2'-one

ID: ALA5188455

PubChem CID: 168278712

Max Phase: Preclinical

Molecular Formula: C22H22N4O2

Molecular Weight: 374.44

Names and Identifiers

Canonical SMILES:  CN1CCC(O/N=C2C(=C3/C(=O)Nc4ccccc43)/Nc3ccccc3/2)CC1

Standard InChI:  InChI=1S/C22H22N4O2/c1-26-12-10-14(11-13-26)28-25-20-16-7-3-5-9-18(16)23-21(20)19-15-6-2-4-8-17(15)24-22(19)27/h2-9,14,23H,10-13H2,1H3,(H,24,27)/b21-19-,25-20+

Standard InChI Key:  STYZRNSOORYOAO-GRXPJKNZSA-N

Molfile:  

 
     RDKit          2D

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    1.0021   -0.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2458   -1.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0504   -1.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625    0.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -2.1378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3854   -2.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0335   -1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4275   -1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -1.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -2.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483   -2.5250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105   -2.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6122   -2.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6122   -1.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9123   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2183   -0.4503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897    0.1211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806    0.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1762   -3.2437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1521    1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9429    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1622    2.4631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4091    1.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1999    1.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    3.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  2  1  0
  3  4  2  0
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  5  6  2  0
  6  1  1  0
  4  7  1  0
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  3  9  1  0
  9 10  2  0
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 19 20  1  0
 21 20  1  0
  8 22  2  0
 23 21  1  0
 24 23  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 21 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5188455

   ---

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: 374.44

Molecular Weight (Monoisotopic): 374.1743

AlogP: 3.29

#Rotatable Bonds: 2

Polar Surface Area: 65.96

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.70

CX Basic pKa: 8.92

CX LogP: 2.20

CX LogD: 0.66

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -0.01

References

1. Lee SB, Chang TY, Lee NZ, Yu ZY, Liu CY, Lee HY..  (2022)  Design, synthesis and biological evaluation of bisindole derivatives as anticancer agents against Tousled-like kinases.,  227  [PMID:34662748] [10.1016/j.ejmech.2021.113904]

2. Miknis, Greg F; Stevens, Sarah J; Smith, Luke E; Ostrov, David A and Churchill, Mair E A.  2015-02-15  Development of novel Asf1-H3/H4 inhibitors.  [PMID:25582598]

Source

Source(1):

• Scientific Literature