(4-(4-(Cyclopropylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)-2-fluoro-5-methoxyphenyl)(morpholino)methanone

ID: ALA2178135

PubChem CID: 71451847

Max Phase: Preclinical

Molecular Formula: C20H21F4N5O3

Molecular Weight: 455.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)N2CCOCC2)c(F)cc1Nc1ncc(C(F)(F)F)c(NC2CC2)n1

Standard InChI:  InChI=1S/C20H21F4N5O3/c1-31-16-8-12(18(30)29-4-6-32-7-5-29)14(21)9-15(16)27-19-25-10-13(20(22,23)24)17(28-19)26-11-2-3-11/h8-11H,2-7H2,1H3,(H2,25,26,27,28)

Standard InChI Key:  FKNAWDCGDQUZRV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   24.4621  -31.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7481  -31.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0464  -30.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7522  -30.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4607  -28.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4595  -29.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1676  -29.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8772  -29.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8744  -28.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1658  -27.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1674  -30.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4596  -30.6472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8750  -30.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0430  -31.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1633  -26.9670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8698  -26.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5766  -26.9652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2826  -26.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2806  -25.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5667  -25.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8637  -25.7431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9914  -26.9620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9866  -25.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6960  -25.7310    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.9831  -24.5082    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.6884  -24.9120    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.9934  -27.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7529  -27.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7527  -26.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5856  -29.4196    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.5908  -28.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4079  -28.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  7 11  1  0
 11 12  1  0
 11 13  2  0
 12  4  1  0
 12  1  1  0
  4  3  1  0
  3 14  1  0
 14  2  1  0
  2  1  1  0
 10 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 18 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 22 27  1  0
  5 28  1  0
 28 29  1  0
  8 30  1  0
 31 27  1  0
 32 31  1  0
 27 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2178135

   (4-{[4-(Cyclopropylamino)-5-(Trifluoromethyl)pyrimidin-2-Yl]amino}-2-Fluoro-5-Methoxyphenyl)(Morpholin-4-Yl)methanone

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: 455.41

Molecular Weight (Monoisotopic): 455.1581

AlogP: 3.43

#Rotatable Bonds: 6

Polar Surface Area: 88.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.38

CX Basic pKa: 3.38

CX LogP: 2.64

CX LogD: 2.64

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.65

Np Likeness Score: -1.74

References

1. Estrada AA, Liu X, Baker-Glenn C, Beresford A, Burdick DJ, Chambers M, Chan BK, Chen H, Ding X, DiPasquale AG, Dominguez SL, Dotson J, Drummond J, Flagella M, Flynn S, Fuji R, Gill A, Gunzner-Toste J, Harris SF, Heffron TP, Kleinheinz T, Lee DW, Le Pichon CE, Lyssikatos JP, Medhurst AD, Moffat JG, Mukund S, Nash K, Scearce-Levie K, Sheng Z, Shore DG, Tran T, Trivedi N, Wang S, Zhang S, Zhang X, Zhao G, Zhu H, Sweeney ZK..  (2012)  Discovery of highly potent, selective, and brain-penetrable leucine-rich repeat kinase 2 (LRRK2) small molecule inhibitors.,  55  (22): [PMID:22985112] [10.1021/jm301020q]

Source

Source(1):

• Scientific Literature