7'-Bromo-1'-methyl-1H,1'H-[2,3']biindolylidene-3,2'-dione 3-[O-(2-piperazin-1-yl-ethyl)-oxime]

ID: ALA4069100

PubChem CID: 135423845

Max Phase: Preclinical

Molecular Formula: C23H26BrCl2N5O2

Molecular Weight: 482.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)/C(=C2\Nc3ccccc3\C2=N/OCCN2CCNCC2)c2cccc(Br)c21.Cl.Cl

Standard InChI:  InChI=1S/C23H24BrN5O2.2ClH/c1-28-22-16(6-4-7-17(22)24)19(23(28)30)21-20(15-5-2-3-8-18(15)26-21)27-31-14-13-29-11-9-25-10-12-29;;/h2-8,25-26H,9-14H2,1H3;2*1H/b21-19-,27-20+;;

Standard InChI Key:  LNOJXOOIUXLWEU-BEDCTKBTSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    4.9107  -14.8893    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4269  -20.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4258  -21.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1402  -21.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1384  -20.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8534  -20.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8536  -21.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437  -21.5511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1317  -20.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433  -20.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8977  -19.4230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9563  -20.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4395  -21.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2236  -21.2908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4390  -20.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270  -20.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8405  -19.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6671  -19.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749  -18.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2648  -19.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1843  -22.3298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3458  -18.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6250  -20.1673    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.8897  -21.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6004  -18.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0485  -17.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3030  -16.6293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1089  -16.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3642  -15.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8152  -15.0599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074  -15.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486  -16.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7137  -17.4005    0.0000 Cl  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
 14 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  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: 482.38

Molecular Weight (Monoisotopic): 481.1113

AlogP: 2.89

#Rotatable Bonds: 4

Polar Surface Area: 69.20

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.82

CX Basic pKa: 9.20

CX LogP: 2.16

CX LogD: 0.48

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -0.40

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