2-[4-(2,2-dibromo-acetyl)-phenyl]-3a,4,9,9atetrahydro-4,9-benzeno-benz[f]isoindole-1,3-dione

ID: ALA1097588

PubChem CID: 46193397

Max Phase: Preclinical

Molecular Formula: C26H17Br2NO3

Molecular Weight: 551.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(N2C(=O)C3C4c5ccccc5C(c5ccccc54)C3C2=O)cc1)C(Br)Br

Standard InChI:  InChI=1S/C26H17Br2NO3/c27-24(28)23(30)13-9-11-14(12-10-13)29-25(31)21-19-15-5-1-2-6-16(15)20(22(21)26(29)32)18-8-4-3-7-17(18)19/h1-12,19-22,24H

Standard InChI Key:  YMFAPICYRIGBPP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
    7.9977    0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6760    0.5650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4500    1.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3799    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3685   -0.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0717   -1.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7839   -0.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7886    0.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0849    0.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4884   -1.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4822   -1.9080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1992   -0.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9517    1.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9686   -0.7073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3583    0.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6393    1.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9893    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5305    0.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8350    2.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5232    2.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4674    3.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239    3.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0354    3.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0946    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7301    0.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5033    1.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7009    1.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1248    0.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3563    0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1581   -0.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9037   -1.1018    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.2055    0.1294    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  6  7  2  0
 16 17  1  0
 18 15  1  0
  3 16  1  0
 17 20  1  0
  7  8  1  0
 25 18  1  0
 15  1  1  0
  8  9  2  0
 19 20  2  0
  9  4  1  0
 20 21  1  0
  2  4  1  0
 21 22  2  0
  7 10  1  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 10 11  2  0
  4  5  2  0
 25 26  2  0
 10 12  1  0
 26 27  1  0
  1  2  1  0
 27 28  2  0
  3 13  2  0
 28 29  1  0
  5  6  1  0
 29 30  2  0
 30 25  1  0
 17 26  1  0
 19 18  1  0
  1 14  2  0
 12 31  1  0
 15 16  1  0
 12 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097588

   17-[4-(2,2-Dibromoacetyl)phenyl]-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione

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: 551.23

Molecular Weight (Monoisotopic): 548.9575

AlogP: 5.38

#Rotatable Bonds: 3

Polar Surface Area: 54.45

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.48

CX LogD: 4.48

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.25

Np Likeness Score: -0.44

References

1. Khalil AM, Berghot MA, Gouda MA..  (2010)  Synthesis and study of some new 1,3-isoindoledione derivatives as potential antibacterial agents.,  45  (4): [PMID:20117862] [10.1016/j.ejmech.2009.12.064]

Source

Source(1):

• Scientific Literature