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

ID: ALA189691

PubChem CID: 5330135

Max Phase: Preclinical

Molecular Formula: C31H45N7O3

Molecular Weight: 563.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)cc(-c2cc3cnc(NCCCCCN4CCN(C)CC4)cc3nc2NC(=O)NC(C)(C)C)c1

Standard InChI:  InChI=1S/C31H45N7O3/c1-31(2,3)36-30(39)35-29-26(22-16-24(40-5)19-25(17-22)41-6)18-23-21-33-28(20-27(23)34-29)32-10-8-7-9-11-38-14-12-37(4)13-15-38/h16-21H,7-15H2,1-6H3,(H,32,33)(H2,34,35,36,39)

Standard InChI Key:  LUPSYDSJDYGOGY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.7083    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8500    0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1458   -5.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4333   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167    3.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542    1.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1458   -5.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542    0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708   -1.8042    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
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 11 18  1  0
 12 10  1  0
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 14 26  1  0
 15 31  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 15  1  0
 28 15  1  0
 29 21  1  0
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 31 39  1  0
 32 14  1  0
 33 23  1  0
 34 23  1  0
 35 23  1  0
 36 24  1  0
 37 30  1  0
 38 29  1  0
 39 41  1  0
 40 36  1  0
 41 40  1  0
  9  7  1  0
 20 21  1  0
 11 12  2  0
 25 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA189691

   1,6-Naphthyridine 25

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: 563.75

Molecular Weight (Monoisotopic): 563.3584

AlogP: 5.06

#Rotatable Bonds: 11

Polar Surface Area: 103.88

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.59

CX Basic pKa: 8.47

CX LogP: 3.98

CX LogD: 2.78

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.28

Np Likeness Score: -1.01

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