1-[7-(4-Diethylamino-butylamino)-3-(3,5-dimethoxy-phenyl)-[1,6]naphthyridin-2-yl]-3-ethyl-urea

ID: ALA190389

PubChem CID: 5330132

Max Phase: Preclinical

Molecular Formula: C27H38N6O3

Molecular Weight: 494.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)Nc1nc2cc(NCCCCN(CC)CC)ncc2cc1-c1cc(OC)cc(OC)c1

Standard InChI:  InChI=1S/C27H38N6O3/c1-6-28-27(34)32-26-23(19-13-21(35-4)16-22(14-19)36-5)15-20-18-30-25(17-24(20)31-26)29-11-9-10-12-33(7-2)8-3/h13-18H,6-12H2,1-5H3,(H,29,30)(H2,28,31,32,34)

Standard InChI Key:  QTMASMKMHNYBIC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
    1.9750   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -0.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -0.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833    0.8083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042    2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -1.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -1.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -0.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1750   -3.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417    0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042    3.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1750   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6000   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    3.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875   -1.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -4.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -2.9167    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  4  1  0
  6  3  1  0
  7  2  1  0
  8  4  2  0
  9  8  1  0
 10  6  2  0
 11 15  1  0
 12 10  1  0
 13  5  2  0
 14  5  1  0
 15  9  2  0
 16 17  1  0
 17 14  2  0
 18 13  1  0
 19  7  2  0
 20  7  1  0
 21 12  1  0
 22 28  1  0
 23 18  1  0
 24 17  1  0
 25 20  1  0
 26 22  1  0
 27 22  1  0
 28 32  1  0
 29 21  1  0
 30 24  1  0
 31 23  1  0
 32 33  1  0
 33 29  1  0
 34 26  1  0
 35 27  1  0
 36 25  1  0
  9  6  1  0
 18 16  2  0
 11 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA190389

   1,6-Naphthyridine 22

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: 494.64

Molecular Weight (Monoisotopic): 494.3005

AlogP: 4.99

#Rotatable Bonds: 13

Polar Surface Area: 100.64

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.61

CX Basic pKa: 10.30

CX LogP: 3.53

CX LogD: 0.87

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: -1.12

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