7'-Bromo-2'-oxo-3-[2-piperazin-1-yl-ethoxyimino]-1,3,1',2'-tetrahydro-[2,3']biindolylidene-5-carboxylic acid methyl ester

ID: ALA4067811

PubChem CID: 137631957

Max Phase: Preclinical

Molecular Formula: C24H24BrN5O4

Molecular Weight: 526.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc2c(c1)C(=N\OCCN1CCNCC1)/C(=C1/C(=O)Nc3c(Br)cccc31)N2

Standard InChI:  InChI=1S/C24H24BrN5O4/c1-33-24(32)14-5-6-18-16(13-14)21(29-34-12-11-30-9-7-26-8-10-30)22(27-18)19-15-3-2-4-17(25)20(15)28-23(19)31/h2-6,13,26-27H,7-12H2,1H3,(H,28,31)/b22-19-,29-21+

Standard InChI Key:  BILFEHXROMPCSG-KCSCLGDBSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    2.4790   -8.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4779   -9.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1859   -9.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1842   -8.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -8.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6756   -8.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -7.6771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769   -9.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4558   -9.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2329   -9.5282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4554   -8.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2363   -8.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8443   -8.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2827   -7.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2029  -10.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6219   -8.4147    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7712   -8.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7710   -7.4869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -8.7129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -8.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3809   -7.0700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331   -6.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0861   -5.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3384   -4.9083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1371   -4.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902   -3.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8461   -3.3530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0454   -3.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889   -4.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
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  9  5  1  0
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 12 20  2  0
 16 21  1  0
  1 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 10 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 34  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4067811

   ---

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: 526.39

Molecular Weight (Monoisotopic): 525.1012

AlogP: 2.65

#Rotatable Bonds: 5

Polar Surface Area: 104.29

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.23

CX Basic pKa: 9.17

CX LogP: 2.16

CX LogD: 0.62

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.24

Np Likeness Score: -0.46

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