6-amino-2-(4-(aminomethyl)-4-methylpiperidin-1-yl)-5-(2,3-dichlorophenylthio)-3-methylpyrimidin-4(3H)-one

ID: ALA4533113

PubChem CID: 124150663

Max Phase: Preclinical

Molecular Formula: C18H23Cl2N5OS

Molecular Weight: 428.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(N2CCC(C)(CN)CC2)nc(N)c(Sc2cccc(Cl)c2Cl)c1=O

Standard InChI:  InChI=1S/C18H23Cl2N5OS/c1-18(10-21)6-8-25(9-7-18)17-23-15(22)14(16(26)24(17)2)27-12-5-3-4-11(19)13(12)20/h3-5H,6-10,21-22H2,1-2H3

Standard InChI Key:  BHGFUFNIOHAHFW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.1666  -11.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3494  -11.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7580  -12.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9879   -9.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9868  -10.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948  -10.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4045  -10.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4016   -9.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6930   -9.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906   -8.4977    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2801   -9.3153    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1078   -9.3089    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170   -9.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175  -10.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227  -10.9350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2313  -10.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2302   -9.7091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5205   -9.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9378  -10.9328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9358  -11.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6394  -12.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3515  -10.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6434  -10.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -8.4816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1102  -10.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227  -11.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3494  -13.1656    0.0000 N   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
  9 10  1  0
  4 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 13 18  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 19 20  1  0
 19 23  1  0
 20 21  1  0
 21  2  1  0
  2 22  1  0
 22 23  1  0
 16 19  1  0
 18 24  1  0
 14 25  2  0
 15 26  1  0
  3 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4533113

   ---

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: 428.39

Molecular Weight (Monoisotopic): 427.1000

AlogP: 3.39

#Rotatable Bonds: 4

Polar Surface Area: 90.17

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.61

CX LogP: 2.77

CX LogD: 0.61

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -0.81

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