US9067937, 94

ID: ALA3692820

Max Phase: Preclinical

Molecular Formula: C25H28Cl2N4O2

Molecular Weight: 487.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1cnc2ccc(-c3cc(Cl)c(O)c(Cl)c3)nc2c1N[C@H]1CC[C@@H](CN(C)C)CC1

Standard InChI:  InChI=1S/C25H28Cl2N4O2/c1-14(32)18-12-28-22-9-8-21(16-10-19(26)25(33)20(27)11-16)30-24(22)23(18)29-17-6-4-15(5-7-17)13-31(2)3/h8-12,15,17,33H,4-7,13H2,1-3H3,(H,28,29)/t15-,17+

Standard InChI Key:  DKZYXHCYPUVGAF-WOVMCDHWSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
   10.1303    1.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0920    0.7680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0940   -0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7907    1.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4920    0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1903    1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8939    0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007   -1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4972   -0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -5.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5969   -6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945   -7.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6327   -8.1046    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -8.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -9.4509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0036   -7.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0438   -8.0971    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0012   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    2.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375    0.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  5  1  0
  8 11  1  1
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 12  1  0
 21 16  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 30 22  1  0
 13 31  1  0
 31 32  2  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3692820

   ---

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: 487.43

Molecular Weight (Monoisotopic): 486.1589

AlogP: 6.04

#Rotatable Bonds: 6

Polar Surface Area: 78.35

Molecular Species: ZWITTERION

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.12

CX Basic pKa: 9.29

CX LogP: 4.06

CX LogD: 4.06

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: -0.97

References

1.  (2015)  1,5-naphthyridine derivatives and MELK inhibitors containing the same, 

Source

Source(1):

• BindingDB Database