5',6'-Dichloro-1H,1'H-[2,3']biindolylidene-3,2'-dione

ID: ALA4065106

Max Phase: Preclinical

Molecular Formula: C16H8Cl2N2O2

Molecular Weight: 331.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2cc(Cl)c(Cl)cc2/C1=C1/Nc2ccccc2C1=O

Standard InChI:  InChI=1S/C16H8Cl2N2O2/c17-9-5-8-12(6-10(9)18)20-16(22)13(8)14-15(21)7-3-1-2-4-11(7)19-14/h1-6,19H,(H,20,22)/b14-13-

Standard InChI Key:  MYUCRYLGBXDIEB-YPKPFQOOSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   27.8656   -1.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8645   -2.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5725   -3.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5707   -1.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2794   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2796   -2.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0626   -2.8938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5463   -2.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0622   -1.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3145   -0.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3635   -2.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8424   -2.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6195   -2.6358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8419   -1.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6229   -1.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2309   -1.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0591   -0.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2739   -0.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6693   -0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5895   -3.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6646    0.0845    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.0997    0.5829    0.0000 Cl  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
 18 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4065106

   ---

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: 331.16

Molecular Weight (Monoisotopic): 329.9963

AlogP: 3.97

#Rotatable Bonds: ┄

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.69

CX Basic pKa: ┄

CX LogP: 3.64

CX LogD: 3.64

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.72

Np Likeness Score: 0.08

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