6'-bromo-5'-methyl-2,3'-biindole-2',3(1H,1'H)-dione 3-(O-acetyloxime)

ID: ALA4094305

Max Phase: Preclinical

Molecular Formula: C19H14BrN3O3

Molecular Weight: 412.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O/N=C1C(=C2/C(=O)Nc3cc(Br)c(C)cc32)/Nc2ccccc2/1

Standard InChI:  InChI=1S/C19H14BrN3O3/c1-9-7-12-15(8-13(9)20)22-19(25)16(12)18-17(23-26-10(2)24)11-5-3-4-6-14(11)21-18/h3-8,21H,1-2H3,(H,22,25)/b18-16-,23-17+

Standard InChI Key:  LQKYIKKSTNBSJC-IMVJFLJXSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   19.1118  -20.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1106  -21.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8187  -21.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8169  -20.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5255  -20.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5258  -21.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3087  -21.5035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7924  -20.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3083  -20.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5606  -19.3943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6096  -20.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0886  -21.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8657  -21.2454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0881  -20.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8691  -20.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4770  -19.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3053  -19.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5201  -18.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9155  -19.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8356  -22.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9108  -18.5290    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   21.0136  -18.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3458  -18.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2659  -18.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7189  -17.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0652  -17.8398    0.0000 O   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
  9 10  2  0
  8 11  2  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 14 11  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 12 20  2  0
 17 21  1  0
 10 22  1  0
 18 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094305

   ---

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: 412.24

Molecular Weight (Monoisotopic): 411.0219

AlogP: 3.81

#Rotatable Bonds: 1

Polar Surface Area: 79.79

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.67

CX Basic pKa: 2.33

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.42

Np Likeness Score: -0.04

References

1. Gaboriaud-Kolar N, Myrianthopoulos V, Vougogiannopoulou K, Gerolymatos P, Horne DA, Jove R, Mikros E, Nam S, Skaltsounis AL..  (2016)  Natural-Based Indirubins Display Potent Cytotoxicity toward Wild-Type and T315I-Resistant Leukemia Cell Lines.,  79  (10): [PMID:27726390] [10.1021/acs.jnatprod.6b00285]

Source

Source(1):

• Scientific Literature