2-(4-(aminomethyl)-4-methylpiperidin-1-yl)-5-((2-(trifluoromethyl)pyridin-3-yl)thio)pyrimidin-4(3H)-one

ID: ALA4523033

PubChem CID: 124150360

Max Phase: Preclinical

Molecular Formula: C17H20F3N5OS

Molecular Weight: 399.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(CN)CCN(c2ncc(Sc3cccnc3C(F)(F)F)c(=O)[nH]2)CC1

Standard InChI:  InChI=1S/C17H20F3N5OS/c1-16(10-21)4-7-25(8-5-16)15-23-9-12(14(26)24-15)27-11-3-2-6-22-13(11)17(18,19)20/h2-3,6,9H,4-5,7-8,10,21H2,1H3,(H,23,24,26)

Standard InChI Key:  OWJVXNYVTUXGIY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   18.2011  -12.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3839  -12.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7925  -13.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0224  -10.5946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0213  -11.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7293  -11.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4390  -11.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4361  -10.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7275  -10.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1423  -10.1797    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.8515  -10.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8520  -11.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5572  -11.8059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2658  -11.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2647  -10.5800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5550  -10.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9723  -11.8036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9703  -12.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6739  -13.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3860  -11.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6779  -11.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1447  -11.8093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3839  -14.0365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7251   -9.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4316   -8.9578    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.0162   -8.9620    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.7172   -8.5475    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 16  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 17 18  1  0
 17 21  1  0
 18 19  1  0
 19  2  1  0
  2 20  1  0
 20 21  1  0
 14 17  1  0
 12 22  2  0
  3 23  1  0
  9 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4523033

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 399.44

Molecular Weight (Monoisotopic): 399.1341

AlogP: 2.90

#Rotatable Bonds: 4

Polar Surface Area: 87.90

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.97

CX Basic pKa: 9.62

CX LogP: 1.01

CX LogD: 0.40

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -0.92

References

1. Sarver P, Acker M, Bagdanoff JT, Chen Z, Chen YN, Chan H, Firestone B, Fodor M, Fortanet J, Hao H, Hentemann M, Kato M, Koenig R, LaBonte LR, Liu G, Liu S, Liu C, McNeill E, Mohseni M, Sendzik M, Stams T, Spence S, Tamez V, Tichkule R, Towler C, Wang H, Wang P, Williams SL, Yu B, LaMarche MJ..  (2019)  6-Amino-3-methylpyrimidinones as Potent, Selective, and Orally Efficacious SHP2 Inhibitors.,  62  (4): [PMID:30688459] [10.1021/acs.jmedchem.8b01726]

Source

Source(1):

• Scientific Literature