N*7*-(4-Diethylamino-butyl)-3-(3,5-dimethoxy-phenyl)-[1,6]naphthyridine-2,7-diamine

ID: ALA188978

PubChem CID: 5330131

Max Phase: Preclinical

Molecular Formula: C24H33N5O2

Molecular Weight: 423.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCCCNc1cc2nc(N)c(-c3cc(OC)cc(OC)c3)cc2cn1

Standard InChI:  InChI=1S/C24H33N5O2/c1-5-29(6-2)10-8-7-9-26-23-15-22-18(16-27-23)13-21(24(25)28-22)17-11-19(30-3)14-20(12-17)31-4/h11-16H,5-10H2,1-4H3,(H2,25,28)(H,26,27)

Standard InChI Key:  CWWGWUITOJWIQB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    5.3750   -0.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292    0.5250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042    1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2375    1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167    2.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2375    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125   -0.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -0.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -4.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167    3.0083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9542    0.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -4.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -4.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292    3.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9542   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -4.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  1  0
  5  1  1  0
  6  7  1  0
  7  5  1  0
  8  5  2  0
  9 10  2  0
 10  8  1  0
 11  4  2  0
 12  4  1  0
 13  7  2  0
 14 15  1  0
 15 12  2  0
 16 11  1  0
 17  2  1  0
 18 10  1  0
 19 24  1  0
 20 15  1  0
 21 16  1  0
 22 19  1  0
 23 19  1  0
 24 28  1  0
 25 18  1  0
 26 20  1  0
 27 21  1  0
 28 29  1  0
 29 25  1  0
 30 22  1  0
 31 23  1  0
 13  9  1  0
  3  6  2  0
 16 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA188978

   7-N-[4-(diethylamino)butyl]-3-(3,5-dimethoxyphenyl)-1,6-naphthyridine-2,7-diamine

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: 423.56

Molecular Weight (Monoisotopic): 423.2634

AlogP: 4.43

#Rotatable Bonds: 11

Polar Surface Area: 85.53

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.32

CX LogP: 3.39

CX LogD: 0.56

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -0.79

References

1. Thompson AM, Delaney AM, Hamby JM, Schroeder MC, Spoon TA, Crean SM, Showalter HD, Denny WA..  (2005)  Synthesis and structure-activity relationships of soluble 7-substituted 3-(3,5-dimethoxyphenyl)-1,6-naphthyridin-2-amines and related ureas as dual inhibitors of the fibroblast growth factor receptor-1 and vascular endothelial growth factor receptor-2 tyrosine kinases.,  48  (14): [PMID:16000000] [10.1021/jm0500931]

Source

Source(1):

• Scientific Literature