7'-Bromo-2'-oxo-3-[(E)-2-piperazin-1-yl-ethoxyimino]-1,3,1',2'-tetrahydro-[2,3']biindolylidene-5-carboxylic acid

ID: ALA4089191

PubChem CID: 137642552

Max Phase: Preclinical

Molecular Formula: C23H22BrN5O4

Molecular Weight: 512.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2c(Br)cccc2/C1=C1/Nc2ccc(C(=O)O)cc2/C1=N\OCCN1CCNCC1

Standard InChI:  InChI=1S/C23H22BrN5O4/c24-16-3-1-2-14-18(22(30)27-19(14)16)21-20(28-33-11-10-29-8-6-25-7-9-29)15-12-13(23(31)32)4-5-17(15)26-21/h1-5,12,25-26H,6-11H2,(H,27,30)(H,31,32)/b21-18-,28-20+

Standard InChI Key:  UZACIMFYWHFQRU-RYSSSEDHSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
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    2.9979  -23.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060  -23.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1956  -22.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4479  -21.5941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4969  -23.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9759  -23.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7530  -23.4452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9754  -22.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7564  -22.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4074  -21.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8028  -21.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7229  -24.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1419  -22.3317    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.2913  -22.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911  -21.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837  -22.6299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9009  -20.9870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1532  -20.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6062  -19.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8585  -18.8254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6572  -18.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9102  -17.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3661  -17.2700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5655  -17.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3090  -18.2171    0.0000 C   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
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  9  5  1  0
  9 10  2  0
  8 11  2  0
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 19 14  1  0
 12 20  2  0
 16 21  1  0
  1 22  1  0
 22 23  2  0
 22 24  1  0
 10 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089191

   ---

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: 512.36

Molecular Weight (Monoisotopic): 511.0855

AlogP: 2.56

#Rotatable Bonds: 5

Polar Surface Area: 115.29

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.59

CX Basic pKa: 9.17

CX LogP: -0.39

CX LogD: -0.40

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.28

Np Likeness Score: -0.37

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