4,6-Dimethyl-N-(3-pyridin-2-yl-isoquinolin-1-yl)-pyrimidine-2-carboxamidine

ID: ALA148401

PubChem CID: 44363627

Max Phase: Preclinical

Molecular Formula: C21H18N6

Molecular Weight: 354.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: DNDI1417606 | 4,6-Dimethyl-N'-(3-Pyridin-2-Ylisoquinolin-1-Yl)pyrimidine-2-Carboximidamide|CHEMBL148401|DNDI1417606|Q27449901|4,6-dimethyl-N'-[3-(pyridin-2-yl)isoquinolin-1-yl]pyrimidine-2-carboximidamide|4,6-dimethyl-N-(3-(pyridin-2-yl)isoquinoline-1-yl)-pyrimidine-2-carboximidamide

Canonical SMILES:  Cc1cc(C)nc(C(=N)Nc2nc(-c3ccccn3)cc3ccccc23)n1

Standard InChI:  InChI=1S/C21H18N6/c1-13-11-14(2)25-21(24-13)19(22)27-20-16-8-4-3-7-15(16)12-18(26-20)17-9-5-6-10-23-17/h3-12H,1-2H3,(H2,22,26,27)

Standard InChI Key:  YKSJLEVXPOMXPZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.7667   -6.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -6.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -8.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -5.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -7.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -8.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -8.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -5.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2000   -9.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -9.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -4.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9042   -4.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -9.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -6.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -6.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6167   -4.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500   -9.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -9.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1875   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6167   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292   -5.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4  1  2  0
  5  2  1  0
  6  3  2  0
  7  3  1  0
  8  4  1  0
  9  1  1  0
 10 11  1  0
 11  9  2  0
 12  7  2  0
 13  6  1  0
 14  8  1  0
 15 14  2  0
 16 12  1  0
 17  5  2  0
 18 11  1  0
 19  9  1  0
 20 15  1  0
 21 13  1  0
 22 12  1  0
 23 14  1  0
 24 26  1  0
 25 27  1  0
 26 19  2  0
 27 23  2  0
  8 10  2  0
 18 24  2  0
 20 25  2  0
 13 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA148401

   4,6-Dimethyl-N'-(3-Pyridin-2-Ylisoquinolin-1-Yl)pyrimidine-2-Carboximidamide

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: 354.42

Molecular Weight (Monoisotopic): 354.1593

AlogP: 4.14

#Rotatable Bonds: 3

Polar Surface Area: 87.44

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.10

CX LogP: 3.91

CX LogD: 3.91

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.43

Np Likeness Score: -0.79

References

1. de Zwart MA, van der Goot H, Timmerman H..  (1989)  Synthesis and copper-dependent antimycoplasmal activity of 1-amino-3-(2-pyridyl)isoquinoline derivatives. 2. Amidines.,  32  (2): [PMID:2913309] [10.1021/jm00122a033]

2. Melissa L. Sykes, Jonathan B. Baell, Marcel Kaiser, Eric Chatelain, Danny Ganame, Jean-Robert Ioset, Vicky M Avery. WEHI/Eskitis Trypanosoma b. brucei screening data,  [10.6019/CHEMBL2094269]

Source

Source(2):

• Scientific Literature
• Drugs for Neglected Diseases Initiative (DNDi)