3,4-Dichloro-N-(3-pyridin-2-yl-isoquinolin-1-yl)-benzamide

ID: ALA131532

PubChem CID: 14040416

Max Phase: Preclinical

Molecular Formula: C21H13Cl2N3O

Molecular Weight: 394.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc(-c2ccccn2)cc2ccccc12)c1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C21H13Cl2N3O/c22-16-9-8-14(11-17(16)23)21(27)26-20-15-6-2-1-5-13(15)12-19(25-20)18-7-3-4-10-24-18/h1-12H,(H,25,26,27)

Standard InChI Key:  WGGSIPLPGMJBIF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.2917   -0.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333   -1.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292    0.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -1.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -2.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -3.5292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -4.1292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292    0.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042    1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  1  0
  5  2  1  0
  6  4  1  0
  7  1  1  0
  8  9  1  0
  9  7  1  0
 10 11  2  0
 11  6  1  0
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 19 14  1  0
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  5  8  2  0
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 10 14  1  0
 22 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA131532

   3,4-Dichloro-N-(3-pyridin-2-yl-isoquinolin-1-yl)-benzamide

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: 394.26

Molecular Weight (Monoisotopic): 393.0436

AlogP: 5.86

#Rotatable Bonds: 3

Polar Surface Area: 54.88

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 14.00

CX Basic pKa: 2.96

CX LogP: 5.84

CX LogD: 5.84

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.47

Np Likeness Score: -1.34

References

1. van Muijlwijk-Koezen JE, Timmerman H, Link R, van der Goot H, Ijzerman AP..  (1998)  A novel class of adenosine A3 receptor ligands. 2. Structure affinity profile of a series of isoquinoline and quinazoline compounds.,  41  (21): [PMID:9767637] [10.1021/jm980037i]

2. de Zwart MA, van der Goot H, Timmerman H..  (1988)  Synthesis and copper-dependent antimycoplasmal activity of 1-amino-3-(2-pyridyl)isoquinoline derivatives. 1. Amides.,  31  (4): [PMID:3351847] [10.1021/jm00399a005]

Source

Source(1):

• Scientific Literature