3-Ethoxy-4-((4-(((1s,4s)-4-hydroxy-4-methylcyclohexyl)oxy)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-N,N-dimethylbenzamide

ID: ALA4447336

PubChem CID: 155518978

Max Phase: Preclinical

Molecular Formula: C24H31N5O4

Molecular Weight: 453.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1cc(C(=O)N(C)C)ccc1Nc1nc(O[C@H]2CC[C@@](C)(O)CC2)c2cc[nH]c2n1

Standard InChI:  InChI=1S/C24H31N5O4/c1-5-32-19-14-15(22(30)29(3)4)6-7-18(19)26-23-27-20-17(10-13-25-20)21(28-23)33-16-8-11-24(2,31)12-9-16/h6-7,10,13-14,16,31H,5,8-9,11-12H2,1-4H3,(H2,25,26,27,28)/t16-,24+

Standard InChI Key:  UAOOTSWHWCQUJL-ONEIWYMKSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   34.4912  -12.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3084  -12.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8998  -11.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0183  -12.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7309  -14.9859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7298  -15.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4378  -16.2144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4360  -14.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1446  -14.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1494  -15.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9295  -16.0494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.4068  -15.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9217  -14.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4336  -13.7599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7247  -13.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0217  -16.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3144  -15.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3195  -14.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6130  -14.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9040  -14.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9060  -15.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6131  -16.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6160  -17.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9098  -17.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1961  -14.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1956  -13.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4886  -14.9871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7806  -14.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4890  -15.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7248  -12.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3116  -13.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0209  -13.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2006  -17.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  5  6  2  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
  8 14  1  0
 15 14  1  1
  6 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 22 23  1  0
 23 24  1  0
 20 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 15 30  1  0
 15 32  1  0
 30  4  1  0
  4  2  1  0
  2 31  1  0
 31 32  1  0
 24 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4447336

   ---

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: 453.54

Molecular Weight (Monoisotopic): 453.2376

AlogP: 3.87

#Rotatable Bonds: 7

Polar Surface Area: 112.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.83

CX Basic pKa: 4.66

CX LogP: 3.26

CX LogD: 3.26

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.50

Np Likeness Score: -0.60

References

1. Riggs JR, Elsner J, Cashion D, Robinson D, Tehrani L, Nagy M, Fultz KE, Krishna Narla R, Peng X, Tran T, Kulkarni A, Bahmanyar S, Condroski K, Pagarigan B, Fenalti G, LeBrun L, Leftheris K, Zhu D, Boylan JF..  (2019)  Design and Optimization Leading to an Orally Active TTK Protein Kinase Inhibitor with Robust Single Agent Efficacy.,  62  (9): [PMID:30998356] [10.1021/acs.jmedchem.8b01869]

Source

Source(1):

• Scientific Literature