7'-Bromo-1H,1'H-[2,3']biindolylidene-3,2'-dione 3-[O-(2-diethylamino-ethyl)-oxime]hydrochloride

ID: ALA4064962

Max Phase: Preclinical

Molecular Formula: C22H24BrClN4O2

Molecular Weight: 455.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCO/N=C1C(=C2/C(=O)Nc3c(Br)cccc32)/Nc2ccccc2/1.Cl

Standard InChI:  InChI=1S/C22H23BrN4O2.ClH/c1-3-27(4-2)12-13-29-26-20-14-8-5-6-11-17(14)24-21(20)18-15-9-7-10-16(23)19(15)25-22(18)28;/h5-11,24H,3-4,12-13H2,1-2H3,(H,25,28);1H/b21-18-,26-20+;

Standard InChI Key:  SJQWENBSEQCGBS-NIJXXFCGSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.0629   -2.6584    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1357   -5.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -6.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -7.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8473   -5.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -5.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5628   -6.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3531   -6.9653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412   -6.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -5.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6072   -4.8366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6660   -6.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1493   -6.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9336   -6.7048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1488   -5.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9371   -5.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5507   -5.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3773   -4.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5848   -4.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9746   -4.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8940   -7.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551   -4.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3354   -5.5810    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.3098   -3.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577   -2.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0123   -2.0421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8193   -1.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0748   -1.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175   -0.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4586   -1.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
 10 11  2  0
  9 12  2  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 15 12  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 13 21  2  0
 11 22  1  0
 17 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 30  1  0
 27 28  1  0
 29 30  1  0
M  END

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: 455.36

Molecular Weight (Monoisotopic): 454.1004

AlogP: 4.30

#Rotatable Bonds: 6

Polar Surface Area: 65.96

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.15

CX Basic pKa: 8.37

CX LogP: 3.55

CX LogD: 2.66

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -0.42

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