1-tert-Butyl-3-[3-(3,5-dimethoxy-phenyl)-7-(3-hydroxy-propylamino)-[1,6]naphthyridin-2-yl]-urea

ID: ALA278472

PubChem CID: 5330157

Max Phase: Preclinical

Molecular Formula: C24H31N5O4

Molecular Weight: 453.54

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H31N5O4/c1-24(2,3)29-23(31)28-22-19(15-9-17(32-4)12-18(10-15)33-5)11-16-14-26-21(13-20(16)27-22)25-7-6-8-30/h9-14,30H,6-8H2,1-5H3,(H,25,26)(H2,27,28,29,31)

Standard InChI Key:  JAYZLGOACZERIJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -0.4375   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -1.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2958   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2958   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -2.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625   -0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -2.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6250    1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0208   -1.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542    2.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625    0.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5875   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0208   -2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0750    2.8583    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 16  1  0
 12 10  1  0
 13  5  1  0
 14  6  1  0
 15  6  2  0
 16  9  2  0
 17  5  2  0
 18 20  2  0
 19 14  2  0
 20 15  1  0
 21 13  1  0
 22 12  1  0
 23 19  1  0
 24 20  1  0
 25 27  1  0
 26 28  1  0
 27 22  1  0
 28 25  1  0
 29 21  1  0
 30 21  1  0
 31 21  1  0
 32 24  1  0
 33 23  1  0
  7  9  1  0
 19 18  1  0
 12 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA278472

   1,6-Naphthyridine 75

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: 453.54

Molecular Weight (Monoisotopic): 453.2376

AlogP: 4.03

#Rotatable Bonds: 8

Polar Surface Area: 117.63

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.59

CX Basic pKa: 5.63

CX LogP: 2.46

CX LogD: 2.45

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: -0.73

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