1-tert-Butyl-3-[7-(4-diethylamino-butylamino)-3-(3,5-dimethoxy-phenyl)-[1,6]naphthyridin-2-yl]-urea

ID: ALA191023

PubChem CID: 5330133

Max Phase: Preclinical

Molecular Formula: C29H42N6O3

Molecular Weight: 522.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCCCNc1cc2nc(NC(=O)NC(C)(C)C)c(-c3cc(OC)cc(OC)c3)cc2cn1

Standard InChI:  InChI=1S/C29H42N6O3/c1-8-35(9-2)13-11-10-12-30-26-18-25-21(19-31-26)16-24(20-14-22(37-6)17-23(15-20)38-7)27(32-25)33-28(36)34-29(3,4)5/h14-19H,8-13H2,1-7H3,(H,30,31)(H2,32,33,34,36)

Standard InChI Key:  YMKCMNJQFGEWCA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 38 40  0  0  0  0  0  0  0  0999 V2000
    1.9250    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -0.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -0.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167    1.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292    1.2083    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
   -0.1458   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333    0.8083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -1.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167    2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458    1.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -1.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042    2.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    1.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5250   -0.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500   -3.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042    3.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875    0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7875   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500   -2.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875    3.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792   -4.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958   -4.8917    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 31  1  0
 24 19  1  0
 25 20  1  0
 26 21  1  0
 27 21  1  0
 28 21  1  0
 29 23  1  0
 30 23  1  0
 31 35  1  0
 32 22  1  0
 33 25  1  0
 34 24  1  0
 35 36  1  0
 36 32  1  0
 37 29  1  0
 38 30  1  0
  9  7  1  0
 18 19  1  0
 11 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA191023

   1,6-Naphthyridine 23

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: 522.69

Molecular Weight (Monoisotopic): 522.3318

AlogP: 5.77

#Rotatable Bonds: 12

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: 10.30

CX LogP: 4.22

CX LogD: 1.57

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.26

Np Likeness Score: -1.02

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