6-(2-Phenyl-cyclopropyl)-8-(pyrimidin-2-ylamino)-naphthalene-2-carboxamidine

ID: ALA182959

PubChem CID: 44392413

Max Phase: Preclinical

Molecular Formula: C24H21N5

Molecular Weight: 379.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc2cc(C3CC3c3ccccc3)cc(Nc3ncccn3)c2c1

Standard InChI:  InChI=1S/C24H21N5/c25-23(26)17-8-7-16-11-18(20-14-19(20)15-5-2-1-3-6-15)13-22(21(16)12-17)29-24-27-9-4-10-28-24/h1-13,19-20H,14H2,(H3,25,26)(H,27,28,29)

Standard InChI Key:  CZRSUKWCMUIVJO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   -0.7458   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1125    0.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375    1.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542    0.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458    2.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083   -1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4125   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5 10  1  0
  6 12  1  0
  7  8  1  0
  8  5  1  0
  9  6  1  0
 10  4  2  0
 11 13  1  0
 12 14  2  0
 13 20  1  0
 14  4  1  0
 15  7  2  0
 16  7  1  0
 17 11  2  0
 18  2  1  0
 19 12  1  0
 20 19  2  0
 21 11  1  0
 22 24  1  0
 23 15  1  0
 24 16  2  0
 25 18  1  0
 26 18  2  0
 27 25  2  0
 28 26  1  0
 29 28  2  0
  3  2  1  0
  6  5  2  0
 29 27  1  0
 13  9  2  0
 22 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA182959

   6-(2-Phenylcyclopropyl)-8-(pyrimidin-2-ylamino)-2-naphthimidamide

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: 379.47

Molecular Weight (Monoisotopic): 379.1797

AlogP: 4.93

#Rotatable Bonds: 5

Polar Surface Area: 87.68

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.73

CX Basic pKa: 11.25

CX LogP: 4.13

CX LogD: 1.88

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -0.31

References

1. Bruncko M, McClellan WJ, Wendt MD, Sauer DR, Geyer A, Dalton CR, Kaminski MA, Weitzberg M, Gong J, Dellaria JF, Mantei R, Zhao X, Nienaber VL, Stewart K, Klinghofer V, Bouska J, Rockway TW, Giranda VL..  (2005)  Naphthamidine urokinase plasminogen activator inhibitors with improved pharmacokinetic properties.,  15  (1): [PMID:15582418] [10.1016/j.bmcl.2004.10.026]

2. Brown SP, Muchmore SW..  (2009)  Large-scale application of high-throughput molecular mechanics with Poisson-Boltzmann surface area for routine physics-based scoring of protein-ligand complexes.,  52  (10): [PMID:19385614] [10.1021/jm801444x]

Source

Source(1):

• Scientific Literature