2-chloro-N-(2-(3,5-dichloro-2-hydroxyphenyl)-1H-benzo[d]imidazol-5-yl)benzamide

ID: ALA386447

PubChem CID: 136043861

Max Phase: Preclinical

Molecular Formula: C20H12Cl3N3O2

Molecular Weight: 432.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc2[nH]c(-c3cc(Cl)cc(Cl)c3O)nc2c1)c1ccccc1Cl

Standard InChI:  InChI=1S/C20H12Cl3N3O2/c21-10-7-13(18(27)15(23)8-10)19-25-16-6-5-11(9-17(16)26-19)24-20(28)12-3-1-2-4-14(12)22/h1-9,27H,(H,24,28)(H,25,26)

Standard InChI Key:  CVOZHNOLAFROBK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.4767   -7.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8775   -8.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7017   -8.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249   -7.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180   -6.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952   -6.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4544   -8.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6517   -7.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6181   -5.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6193   -6.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044   -7.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1880   -6.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1909   -5.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9062   -5.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4729   -7.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4716   -7.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7591   -6.6204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439   -7.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -7.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3330   -8.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370   -6.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619   -6.7632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6222   -7.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6157   -7.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733   -8.0984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9046   -7.8610    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1038   -8.8869    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1379   -6.0247    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 14  9  2  0
  2  7  1  0
 12 15  1  0
  3  4  1  0
 15 16  2  0
  1  8  1  0
 15 17  1  0
 17 18  1  0
  4  5  2  0
 18 19  2  0
  9 10  1  0
 19 20  1  0
 20 24  2  0
  2  3  2  0
 23 21  2  0
 21 18  1  0
 23 24  1  0
 10 11  2  0
  5  6  1  0
 11 12  1  0
  6  1  2  0
 22 23  1  0
 24 25  1  0
 25  8  1  0
  8 22  2  0
 12 13  2  0
 11 26  1  0
  1  2  1  0
  3 27  1  0
 13 14  1  0
  5 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA386447

   ---

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: 432.69

Molecular Weight (Monoisotopic): 430.9995

AlogP: 6.15

#Rotatable Bonds: 3

Polar Surface Area: 78.01

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.71

CX Basic pKa: 4.75

CX LogP: 5.76

CX LogD: 5.10

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: -1.48

References

1. Wolkenberg SE, Zhao Z, Kapitskaya M, Webber AL, Petrukhin K, Tang YS, Dean DC, Hartman GD, Lindsley CW..  (2006)  Identification of potent agonists of photoreceptor-specific nuclear receptor (NR2E3) and preparation of a radioligand.,  16  (19): [PMID:16879962] [10.1016/j.bmcl.2006.07.056]

Source

Source(1):

• Scientific Literature