(3S,4S)-8-(7-(2,3-dichlorophenyl)-5H-pyrrolo[2,3-b]pyrazin-3-yl)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine

ID: ALA4475081

PubChem CID: 124148108

Max Phase: Preclinical

Molecular Formula: C21H23Cl2N5O

Molecular Weight: 432.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H]1OCC2(CCN(c3cnc4c(-c5cccc(Cl)c5Cl)c[nH]c4n3)CC2)[C@@H]1N

Standard InChI:  InChI=1S/C21H23Cl2N5O/c1-12-19(24)21(11-29-12)5-7-28(8-6-21)16-10-25-18-14(9-26-20(18)27-16)13-3-2-4-15(22)17(13)23/h2-4,9-10,12,19H,5-8,11,24H2,1H3,(H,26,27)/t12-,19+/m0/s1

Standard InChI Key:  SJLQMBIPYINRMF-HXPMCKFVSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   10.3438  -16.1058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3394  -15.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5608  -15.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0840  -15.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5680  -16.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6366  -15.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292  -14.9905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4105  -16.4039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303  -16.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032  -15.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128  -14.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8674  -14.3798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1206  -14.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2046  -15.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5960  -16.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924  -15.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1836  -16.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1800  -16.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8912  -17.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5970  -16.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978  -14.8372    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4776  -15.6480    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4538  -15.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8611  -16.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6748  -16.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6798  -14.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8600  -14.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3041  -14.2645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9979  -14.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  6  9  1  0
  7 11  1  0
 10  8  1  0
  8  9  2  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 16 21  1  0
 17 22  1  0
  6 23  1  0
 23 24  1  0
 23 27  1  0
 24 25  1  0
 25  4  1  0
  4 26  1  0
 26 27  1  0
  3 28  1  6
  2 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4475081

   ---

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: 432.36

Molecular Weight (Monoisotopic): 431.1280

AlogP: 4.26

#Rotatable Bonds: 2

Polar Surface Area: 80.06

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.47

CX Basic pKa: 9.47

CX LogP: 3.66

CX LogD: 1.63

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: -0.46

References

1. Bagdanoff JT, Chen Z, Acker M, Chen YN, Chan H, Dore M, Firestone B, Fodor M, Fortanet J, Hentemann M, Kato M, Koenig R, LaBonte LR, Liu S, Mohseni M, Ntaganda R, Sarver P, Smith T, Sendzik M, Stams T, Spence S, Towler C, Wang H, Wang P, Williams SL, LaMarche MJ..  (2019)  Optimization of Fused Bicyclic Allosteric SHP2 Inhibitors.,  62  (4): [PMID:30688462] [10.1021/acs.jmedchem.8b01725]

Source

Source(1):

• Scientific Literature