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

ID: ALA365140

PubChem CID: 5330169

Max Phase: Preclinical

Molecular Formula: C23H30N6O4

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)cc(-c2cc3cnc(NCCCO)nc3nc2NC(=O)NC(C)(C)C)c1

Standard InChI:  InChI=1S/C23H30N6O4/c1-23(2,3)29-22(31)28-20-18(14-9-16(32-4)12-17(10-14)33-5)11-15-13-25-21(24-7-6-8-30)27-19(15)26-20/h9-13,30H,6-8H2,1-5H3,(H3,24,25,26,27,28,29,31)

Standard InChI Key:  QOTKZBTTZSPMNH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.5000   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -1.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -1.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -1.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583    0.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -2.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417    1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000    0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417    1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625    1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833   -1.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    2.8083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3000    0.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3500   -3.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2250   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125    3.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  4  2  0
  4  2  1  0
  5  1  1  0
  6  1  1  0
  7  5  1  0
  8 11  1  0
  9  6  1  0
 10  3  1  0
 11  6  2  0
 12 14  1  0
 13  7  1  0
 14  8  2  0
 15  9  1  0
 16  9  2  0
 17  7  2  0
 18 20  2  0
 19 15  2  0
 20 16  1  0
 21 13  1  0
 22 10  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
  4  8  1  0
 19 18  1  0
 10 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA365140

   Pyrido[2,3-d]pyrimidine 105

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: 454.53

Molecular Weight (Monoisotopic): 454.2329

AlogP: 3.42

#Rotatable Bonds: 8

Polar Surface Area: 130.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.52

CX Basic pKa: 4.31

CX LogP: 2.16

CX LogD: 2.16

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: -0.69

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