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

ID: ALA363551

PubChem CID: 5330128

Max Phase: Preclinical

Molecular Formula: C28H40N6O3

Molecular Weight: 508.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCCNc1cc2nc(NC(=O)NC(C)(C)C)c(-c3cc(OC)cc(OC)c3)cc2cn1

Standard InChI:  InChI=1S/C28H40N6O3/c1-8-34(9-2)12-10-11-29-25-17-24-20(18-30-25)15-23(19-13-21(36-6)16-22(14-19)37-7)26(31-24)32-27(35)33-28(3,4)5/h13-18H,8-12H2,1-7H3,(H,29,30)(H2,31,32,33,35)

Standard InChI Key:  SADVQUINRBCGFP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -0.8125    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -0.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -0.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958    1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333    1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708    0.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -1.5875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958    2.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583    1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -1.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292    2.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    2.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292    1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3958   -0.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625   -2.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    3.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3958   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500   -1.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -3.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500   -2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292    3.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500   -4.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5375   -2.8250    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 27  1  0
 24 19  1  0
 25 20  1  0
 26 28  1  0
 27 26  1  0
 28 22  1  0
 29 21  1  0
 30 21  1  0
 31 21  1  0
 32 23  1  0
 33 23  1  0
 34 25  1  0
 35 24  1  0
 36 32  1  0
 37 33  1  0
  7  9  1  0
 19 18  1  0
 12 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA363551

   1,6-Naphthyridine 18

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: 508.67

Molecular Weight (Monoisotopic): 508.3162

AlogP: 5.38

#Rotatable Bonds: 11

Polar Surface Area: 100.64

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.59

CX Basic pKa: 9.93

CX LogP: 3.75

CX LogD: 1.38

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.30

Np Likeness Score: -1.06

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