1-tert-Butyl-3-{3-(3,5-dimethoxy-phenyl)-7-[3-(4-methyl-piperazin-1-yl)-propylamino]-[1,6]naphthyridin-2-yl}-urea

ID: ALA189995

PubChem CID: 5330127

Max Phase: Preclinical

Molecular Formula: C29H41N7O3

Molecular Weight: 535.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)cc(-c2cc3cnc(NCCCN4CCN(C)CC4)cc3nc2NC(=O)NC(C)(C)C)c1

Standard InChI:  InChI=1S/C29H41N7O3/c1-29(2,3)34-28(37)33-27-24(20-14-22(38-5)17-23(15-20)39-6)16-21-19-31-26(18-25(21)32-27)30-8-7-9-36-12-10-35(4)11-13-36/h14-19H,7-13H2,1-6H3,(H,30,31)(H2,32,33,34,37)

Standard InChI Key:  ABQSJCCISLWTEW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.6333   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -1.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458   -1.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875   -0.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042   -2.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833   -3.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458   -4.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000   -0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -2.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167    1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000    1.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083   -1.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -5.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458   -3.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833   -4.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000    2.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -0.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125    2.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  1  0
  5  2  1  0
  6  4  1  0
  7  3  1  0
  8  4  2  0
  9  8  1  0
 10  7  2  0
 11 18  1  0
 12 10  1  0
 13  5  1  0
 14 31  1  0
 15 26  1  0
 16  6  1  0
 17  6  2  0
 18  9  2  0
 19  5  2  0
 20 22  2  0
 21 16  2  0
 22 17  1  0
 23 13  1  0
 24 12  1  0
 25 27  1  0
 26 28  1  0
 27 14  1  0
 28 14  1  0
 29 21  1  0
 30 22  1  0
 31 32  1  0
 32 34  1  0
 33 15  1  0
 34 24  1  0
 35 23  1  0
 36 23  1  0
 37 23  1  0
 38 29  1  0
 39 30  1  0
  9  7  1  0
 20 21  1  0
 11 12  2  0
 25 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA189995

   1,6-Naphthyridine 17

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: 535.69

Molecular Weight (Monoisotopic): 535.3271

AlogP: 4.28

#Rotatable Bonds: 9

Polar Surface Area: 103.88

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.59

CX Basic pKa: 8.10

CX LogP: 3.01

CX LogD: 2.23

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.35

Np Likeness Score: -1.09

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