4-{[({[6'-bromo-2'-oxo-1',2'-dihydro-2,3'-biindol-3(1H)-ylidene]amino}oxy)carbonyl]amino}benzonitrile

ID: ALA4091937

PubChem CID: 137656012

Max Phase: Preclinical

Molecular Formula: C24H14BrN5O3

Molecular Weight: 500.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(NC(=O)O/N=C2C(=C3/C(=O)Nc4cc(Br)ccc43)/Nc3ccccc3/2)cc1

Standard InChI:  InChI=1S/C24H14BrN5O3/c25-14-7-10-16-19(11-14)29-23(31)20(16)22-21(17-3-1-2-4-18(17)28-22)30-33-24(32)27-15-8-5-13(12-26)6-9-15/h1-11,28H,(H,27,32)(H,29,31)/b22-20-,30-21+

Standard InChI Key:  MUDHEWCFRJYKGW-LBEIWGDZSA-N

Molfile:  

     RDKit          2D

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   20.4767  -17.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1848  -17.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.1586  -16.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6744  -16.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9267  -15.3414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9758  -16.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4547  -17.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2318  -17.1925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4542  -16.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2352  -16.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.2816  -15.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2017  -18.2223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3797  -14.7343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2769  -14.4761    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   22.6320  -13.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0850  -13.3499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4313  -13.7868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2857  -13.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7435  -12.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9448  -13.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6919  -13.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2437  -14.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0402  -14.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8928  -14.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0970  -14.2035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  5  4  2  0
  4  1  1  0
  5  6  1  0
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 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 29 32  1  0
 32 33  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091937

   ---

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: 500.31

Molecular Weight (Monoisotopic): 499.0280

AlogP: 5.06

#Rotatable Bonds: 2

Polar Surface Area: 115.61

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.56

CX Basic pKa: 1.80

CX LogP: 4.47

CX LogD: 4.47

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.26

Np Likeness Score: -0.73

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