4-((4-(Cyclopentyloxy)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxy-N,N-dimethylbenzamide

ID: ALA4585148

PubChem CID: 155562324

Max Phase: Preclinical

Molecular Formula: C21H25N5O3

Molecular Weight: 395.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)N(C)C)ccc1Nc1nc(OC2CCCC2)c2cc[nH]c2n1

Standard InChI:  InChI=1S/C21H25N5O3/c1-26(2)20(27)13-8-9-16(17(12-13)28-3)23-21-24-18-15(10-11-22-18)19(25-21)29-14-6-4-5-7-14/h8-12,14H,4-7H2,1-3H3,(H2,22,23,24,25)

Standard InChI Key:  MECVZQUPJAELHS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   21.8481   -5.4190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8470   -6.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5550   -6.6475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5532   -5.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2619   -5.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2667   -6.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0467   -6.4825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5240   -5.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0389   -5.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5508   -4.1930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8419   -3.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7566   -2.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9568   -2.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5503   -3.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0990   -4.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1390   -6.6466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4316   -6.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4368   -5.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7302   -5.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0212   -5.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0232   -6.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7303   -6.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7332   -7.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0270   -7.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3133   -5.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3128   -4.1940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6058   -5.4201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8978   -5.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6062   -6.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  2 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
M  END

Alternative Forms

1. Parent:

   

   ALA4585148

   ---

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: 395.46

Molecular Weight (Monoisotopic): 395.1957

AlogP: 3.73

#Rotatable Bonds: 6

Polar Surface Area: 92.37

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.84

CX Basic pKa: 4.66

CX LogP: 3.57

CX LogD: 3.57

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -1.03

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