12-[1-acetyl-1H-benzimidazol-2-yl]-9,10-dihydro-9,10-ethanoanthracene-11-carboxylic acid

ID: ALA1098579

PubChem CID: 46886845

Max Phase: Preclinical

Molecular Formula: C26H20N2O4

Molecular Weight: 424.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)n1c(C2C3c4ccccc4C(c4ccccc43)C2C(=O)O)nc2ccccc21

Standard InChI:  InChI=1S/C26H20N2O4/c1-32-26(31)28-19-13-7-6-12-18(19)27-24(28)22-20-14-8-2-4-10-16(14)21(23(22)25(29)30)17-11-5-3-9-15(17)20/h2-13,20-23H,1H3,(H,29,30)

Standard InChI Key:  IFLNBOXJWJFGFW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
    6.8148   -7.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8205   -8.5400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5823   -7.4620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0725   -8.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5982   -8.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377   -9.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7513   -9.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2242   -8.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8820   -8.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1488   -7.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439   -6.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3595   -6.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632   -7.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1994   -6.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6863   -5.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3499   -4.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270   -4.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3806   -6.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6915   -8.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2041   -7.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3825   -7.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0471   -8.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5396   -8.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3595   -8.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8510   -6.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5597   -6.4195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8477   -5.1977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4047   -9.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5884   -9.2340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8054   -9.9541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1725   -9.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  3  1  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
 19 14  1  0
  9  4  1  0
  2  5  1  0
 20 21  2  0
  1 10  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
  4  5  2  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
 25 20  1  0
 12 21  1  0
 14 13  1  0
 13 10  1  0
  1  2  1  0
 12 15  1  0
 26 27  1  0
 26 28  2  0
 11 26  1  0
  5  6  1  0
  2 29  1  0
 20 13  1  0
 29 30  1  0
  4  3  1  0
 29 31  2  0
  6  7  2  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098579

   16-(1-Methoxycarbonylbenzimidazol-2-yl)tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylic acid

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: 424.46

Molecular Weight (Monoisotopic): 424.1423

AlogP: 4.73

#Rotatable Bonds: 2

Polar Surface Area: 81.42

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.10

CX Basic pKa: 2.03

CX LogP: 4.28

CX LogD: 1.18

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -0.28

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