1-(5-Carboxy-1H-benzo[d]imidazol-2-ylmethyl)pyridinium chloride

ID: ALA1631256

PubChem CID: 50907898

Max Phase: Preclinical

Molecular Formula: C14H12ClN3O2

Molecular Weight: 254.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc2[nH]c(C[n+]3ccccc3)nc2c1.[Cl-]

Standard InChI:  InChI=1S/C14H11N3O2.ClH/c18-14(19)10-4-5-11-12(8-10)16-13(15-11)9-17-6-2-1-3-7-17;/h1-8H,9H2,(H-,15,16,18,19);1H

Standard InChI Key:  QKIXFJHBTRAWQR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   11.7804   -6.7808    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9226   -6.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9214   -7.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6360   -7.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6342   -6.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3496   -6.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3499   -7.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1401   -7.5453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6285   -6.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1397   -6.2008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4533   -6.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8660   -7.5868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2080   -6.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2078   -5.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938   -6.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4502   -8.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8623   -9.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6880   -9.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1001   -8.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6856   -7.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  6  1  0
  5  2  1  0
  9 11  1  0
  6  7  1  0
 11 12  1  0
  2 13  1  0
  3  4  1  0
 13 14  2  0
  4  7  2  0
 13 15  1  0
  2  3  2  0
 12 16  2  0
  6  5  2  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  9 10  2  0
 19 20  2  0
 20 12  1  0
M  CHG  2   1  -1  12   1
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: 254.27

Molecular Weight (Monoisotopic): 254.0924

AlogP: 1.60

#Rotatable Bonds: 3

Polar Surface Area: 69.86

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.68

CX Basic pKa: 2.74

CX LogP: -2.69

CX LogD: -2.68

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.70

Np Likeness Score: -0.94

References

1. Galal SA, Hegab KH, Hashem AM, Youssef NS..  (2010)  Synthesis and antitumor activity of novel benzimidazole-5-carboxylic acid derivatives and their transition metal complexes as topoisomerease II inhibitors.,  45  (12): [PMID:20884089] [10.1016/j.ejmech.2010.09.023]

2. Liu T, Sun C, Xing X, Jing L, Tan R, Luo Y, Huang W, Song H, Li Z, Zhao Y..  (2012)  Synthesis and evaluation of 2-[2-(phenylthiomethyl)-1H-benzo[d] imidazol-1-yl)acetohydrazide derivatives as antitumor agents.,  22  (9): [PMID:22483608] [10.1016/j.bmcl.2012.03.061]

Source

Source(1):

• Scientific Literature