BATOPROTAFIB

ID: ALA4650521

Cas Number: 1801765-04-7

PubChem CID: 118238370

Product Number: T414310, Order Now?

Max Phase: Phase

Molecular Formula: C18H24ClN7OS

Molecular Weight: 421.96

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Batoprotafib | Ptpn11 inhibitor tno155 | Shp2 inhibitor tno155 | Tno 155 | Tno-155 | Tno155 | TNO-155 | TNO155 | TNO155|1801765-04-7|batoprotafib|FPJWORQEGI|TNO-155|SHP2 inhibitor TNO155|PTPN11 inhibitor TNO155|(3S,4S)-8-[6-amino-5-(2-amino-3-chloropyridin-4-yl)sulfanylpyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine|(3S,4S)-8-[6-Amino-5-[(2-amino-3-chloro-4-pyridinyl)thio]-2-pyrazinyl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine|(3S,4S)-8-(6-Amino-5-((2-amino-3-chloropyridin-4-yl)thio)Show More⌵

Canonical SMILES:  C[C@@H]1OCC2(CCN(c3cnc(Sc4ccnc(N)c4Cl)c(N)n3)CC2)[C@@H]1N

Standard InChI:  InChI=1S/C18H24ClN7OS/c1-10-14(20)18(9-27-10)3-6-26(7-4-18)12-8-24-17(16(22)25-12)28-11-2-5-23-15(21)13(11)19/h2,5,8,10,14H,3-4,6-7,9,20H2,1H3,(H2,21,23)(H2,22,25)/t10-,14+/m0/s1

Standard InChI Key:  UCJZOKGUEJUNIO-IINYFYTJSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -2.0774    2.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919    1.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919    0.7816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774    0.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3630    0.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3630    1.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6485    0.3691    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    0.7816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    1.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6485    2.0191    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    0.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950    0.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950    1.6065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    2.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774   -0.4559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9169    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2024    0.3571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2024   -0.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9169   -0.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6313   -0.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6313    0.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3850   -0.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7176   -1.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5245   -1.4599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9370   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    2.8440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5565    0.6746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7575   -0.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  8  9  2  0
  9 10  1  0
  5  7  1  0
  6 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 11  1  0
  9 14  1  0
  4 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16 21  1  0
 23 24  1  0
 24 25  1  0
 22 25  1  0
 22 20  1  0
 20 23  1  0
 14 26  1  0
 12 17  1  0
 22 27  1  6
 25 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4650521

   TNO155

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: Yes

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.96

Molecular Weight (Monoisotopic): 421.1452

AlogP: 2.17

#Rotatable Bonds: 3

Polar Surface Area: 129.20

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.48

CX LogP: 1.66

CX LogD: -0.38

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -0.49

References

1. Unpublished dataset, 

2. 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]

3. International Nonproprietary Names for Pharmaceutical Substances (INN), 

4. Tang K, Zhao M, Wu YH, Wu Q, Wang S, Dong Y, Yu B, Song Y, Liu HM..  (2022)  Structure-based design, synthesis and biological evaluation of aminopyrazines as highly potent, selective, and cellularly active allosteric SHP2 inhibitors.,  230  [PMID:35063735] [10.1016/j.ejmech.2022.114106]

5. Chen X, Shu C, Li W, Hou Q, Luo G, Yang K, Wu X..  (2022)  Discovery of a Novel Src Homology-2 Domain Containing Protein Tyrosine Phosphatase-2 (SHP2) and Cyclin-Dependent Kinase 4 (CDK4) Dual Inhibitor for the Treatment of Triple-Negative Breast Cancer.,  65  (9.0): [PMID:35447031] [10.1021/acs.jmedchem.2c00063]

6. Zhang J, Zhang Y, Qu B, Yang H, Hu S, Dong X..  (2021)  If small molecules immunotherapy comes, can the prime be far behind?,  218  [PMID:33773287] [10.1016/j.ejmech.2021.113356]

7. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - IncuCyte,  [10.6019/CHEMBL5303304]

8. EUbOPEN.  (2023)  Tm Shift (DSF) assay results for EUbOPEN Chemogenomics Library,  [10.6019/CHEMBL5308504]

Source

Source(4):

• Scientific Literature
• Clinical Candidates
• EUbOPEN Chemogenomic Library
• International Nonproprietary Names