1-(4-(2,3-Dihydro-3-methyl-2-oxo-1H-imidazo[4,5-b]pyridin-7-yl-oxy)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea

ID: ALA523129

Cas Number: 884339-66-6

PubChem CID: 11719900

Max Phase: Preclinical

Molecular Formula: C21H15ClF3N5O3

Molecular Weight: 477.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(=O)[nH]c2c(Oc3ccc(NC(=O)Nc4ccc(Cl)c(C(F)(F)F)c4)cc3)ccnc21

Standard InChI:  InChI=1S/C21H15ClF3N5O3/c1-30-18-17(29-20(30)32)16(8-9-26-18)33-13-5-2-11(3-6-13)27-19(31)28-12-4-7-15(22)14(10-12)21(23,24)25/h2-10H,1H3,(H,29,32)(H2,27,28,31)

Standard InChI Key:  MNCDHOPLKWNXCF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   10.7280  -24.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7268  -25.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4423  -25.5565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4405  -23.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1563  -24.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1612  -25.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9538  -25.3958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4388  -24.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9459  -24.0501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2644  -24.7151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4380  -23.0765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7230  -22.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7310  -21.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0191  -21.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3008  -21.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2986  -22.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0110  -23.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5876  -21.4013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5913  -20.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8781  -20.1596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3082  -20.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1610  -20.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4517  -20.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7350  -20.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361  -21.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4481  -21.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1618  -21.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2135  -26.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195  -21.7899    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.4437  -22.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4385  -23.4480    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2693  -22.6302    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180  -22.6237    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  7  8  1  0
 15 18  1  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 19 21  2  0
  8 10  2  0
 20 22  1  0
  5  6  1  0
 22 23  2  0
  4 11  1  0
 23 24  1  0
 24 25  2  0
 11 12  1  0
 25 26  1  0
  2  3  1  0
 26 27  2  0
 27 22  1  0
 12 13  2  0
  7 28  1  0
  3  6  2  0
 25 29  1  0
 13 14  1  0
 26 30  1  0
  1  2  2  0
 30 31  1  0
 14 15  2  0
 30 32  1  0
  5  4  2  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA523129

   V600Ebraf-IN-1

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: 477.83

Molecular Weight (Monoisotopic): 477.0816

AlogP: 5.37

#Rotatable Bonds: 4

Polar Surface Area: 101.04

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.49

CX Basic pKa: 2.77

CX LogP: 4.69

CX LogD: 4.69

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -1.43

References

1. Niculescu-Duvaz D, Gaulon C, Dijkstra HP, Niculescu-Duvaz I, Zambon A, Ménard D, Suijkerbuijk BM, Nourry A, Davies L, Manne H, Friedlos F, Ogilvie L, Hedley D, Whittaker S, Kirk R, Gill A, Taylor RD, Raynaud FI, Moreno-Farre J, Marais R, Springer CJ..  (2009)  Pyridoimidazolones as novel potent inhibitors of v-Raf murine sarcoma viral oncogene homologue B1 (BRAF).,  52  (8): [PMID:19323560] [10.1021/jm801509w]

Source

Source(1):

• Scientific Literature