4-chloro-3-(cyclohexylmethyl)-2-(4-nitrophenyl)-3H-imidazo[4,5-g]quinoline

ID: ALA3810340

PubChem CID: 127044561

Max Phase: Preclinical

Molecular Formula: C23H21ClN4O2

Molecular Weight: 420.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(-c2nc3cc4cccnc4c(Cl)c3n2CC2CCCCC2)cc1

Standard InChI:  InChI=1S/C23H21ClN4O2/c24-20-21-17(7-4-12-25-21)13-19-22(20)27(14-15-5-2-1-3-6-15)23(26-19)16-8-10-18(11-9-16)28(29)30/h4,7-13,15H,1-3,5-6,14H2

Standard InChI Key:  NXPULCNSBKAYRL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    4.6043   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6043    0.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044    1.5915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924    0.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7168    1.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7168   -1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831    0.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045    1.2999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8792    0.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045   -1.1298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3799    0.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2183    1.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7144    1.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3687   -0.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5270   -1.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0309   -1.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7217    2.7914    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731    2.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9422    3.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134    4.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8823    4.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8800    3.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4088    2.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9400    1.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8655   -0.2461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5406    0.7460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3874   -1.3266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  7 20  1  0
 11 21  1  0
 21 22  1  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 17 28  1  0
 28 29  1  0
 28 30  2  0
M  CHG  2  28   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3810340

   ---

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: 420.90

Molecular Weight (Monoisotopic): 420.1353

AlogP: 6.39

#Rotatable Bonds: 4

Polar Surface Area: 73.85

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.54

CX LogP: 6.32

CX LogD: 6.32

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: -1.27

References

1. Carta A, Briguglio I, Piras S, Corona P, Ibba R, Laurini E, Fermeglia M, Pricl S, Desideri N, Atzori EM, La Colla P, Collu G, Delogu I, Loddo R..  (2016)  A combined in silico/in vitro approach unveils common molecular requirements for efficient BVDV RdRp binding of linear aromatic N-polycyclic systems.,  117  [PMID:27161176] [10.1016/j.ejmech.2016.03.080]

Source

Source(1):

• Scientific Literature