3-((2-amino-3-chloropyridin-4-yl)thio)-6-(4-(aminomethyl)-4-methylpiperidin-1-yl)pyrazin-2-amine

ID: ALA4784611

PubChem CID: 118239411

Max Phase: Preclinical

Molecular Formula: C16H22ClN7S

Molecular Weight: 379.92

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(CN)CCN(c2cnc(Sc3ccnc(N)c3Cl)c(N)n2)CC1

Standard InChI:  InChI=1S/C16H22ClN7S/c1-16(9-18)3-6-24(7-4-16)11-8-22-15(14(20)23-11)25-10-2-5-21-13(19)12(10)17/h2,5,8H,3-4,6-7,9,18H2,1H3,(H2,19,21)(H2,20,23)

Standard InChI Key:  SPLRMLMESIBHAO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    8.0112  -13.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3062  -13.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7202  -13.9897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3059  -14.8065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0149  -15.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7200  -14.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0115  -12.7637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4289  -15.2157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4287  -16.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1376  -16.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8427  -16.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8430  -15.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1381  -14.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1257  -16.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6594  -16.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0653  -15.3209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5982  -13.5811    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907  -13.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1863  -13.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793  -13.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793  -14.8057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1922  -15.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8963  -14.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7716  -13.5790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1880  -12.7621    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  2  4  2  0
  4  5  1  0
  5  6  2  0
  3  6  1  0
  1  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  8 13  1  0
 11 14  1  0
  6  8  1  0
 11 15  1  0
 15 16  1  0
  2 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 20 24  1  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4784611

   US10301278, Example 42

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: 379.92

Molecular Weight (Monoisotopic): 379.1346

AlogP: 2.41

#Rotatable Bonds: 4

Polar Surface Area: 119.97

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.91

CX LogP: 1.99

CX LogD: -0.41

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -0.83

References

1. LaMarche MJ,Acker M,Argintaru A,Bauer D,Boisclair J,Chan H,Chen CH,Chen YN,Chen Z,Deng Z,Dore M,Dunstan D,Fan J,Fekkes P,Firestone B,Fodor M,Garcia-Fortanet J,Fortin PD,Fridrich C,Giraldes J,Glick M,Grunenfelder D,Hao HX,Hentemann M,Ho S,Jouk A,Kang ZB,Karki R,Kato M,Keen N,Koenig R,LaBonte LR,Larrow J,Liu G,Liu S,Majumdar D,Mathieu S,Meyer MJ,Mohseni M,Ntaganda R,Palermo M,Perez L,Pu M,Ramsey T,Reilly J,Sarver P,Sellers WR,Sendzik M,Shultz MD,Slisz J,Slocum K,Smith T,Spence S,Stams T,Straub C,Tamez V,Toure BB,Towler C,Wang P,Wang H,Williams SL,Yang F,Yu B,Zhang JH,Zhu S.  (2020)  Identification of TNO155, an Allosteric SHP2 Inhibitor for the Treatment of Cancer.,  63  (22): [PMID:32910655] [10.1021/acs.jmedchem.0c01170]

Source

Source(1):

• Scientific Literature