4-(5-(1H-Benzo[d]imidazol-6-yl)-4-(cyclopentyloxy)-7H-pyrrolo-[2,3-d]pyrimidin-2-ylamino)-3-methoxy-N-methylbenzamide

ID: ALA4098047

PubChem CID: 117881279

Max Phase: Preclinical

Molecular Formula: C27H27N7O3

Molecular Weight: 497.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1ccc(Nc2nc(OC3CCCC3)c3c(-c4ccc5nc[nH]c5c4)c[nH]c3n2)c(OC)c1

Standard InChI:  InChI=1S/C27H27N7O3/c1-28-25(35)16-8-10-20(22(12-16)36-2)32-27-33-24-23(26(34-27)37-17-5-3-4-6-17)18(13-29-24)15-7-9-19-21(11-15)31-14-30-19/h7-14,17H,3-6H2,1-2H3,(H,28,35)(H,30,31)(H2,29,32,33,34)

Standard InChI Key:  MHQQKTQRYKCSFI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   41.2326  -18.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9406  -19.4007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.9388  -17.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5204  -19.3997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8089  -18.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8141  -18.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1034  -17.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3903  -18.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3923  -18.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   43.4405  -19.2356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.9220  -18.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4328  -17.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1065  -20.2206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   41.9364  -16.9337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.2275  -16.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1381  -15.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3341  -15.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9276  -16.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4804  -16.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6853  -17.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4891  -16.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3764  -15.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1321  -16.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1824  -15.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7371  -16.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4838  -15.8275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.3922  -15.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5889  -14.8455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 13  2  0
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  4  1  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
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 11 17  1  0
 17 18  1  0
  9 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
  4 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
 29 30  2  0
 30 34  1  0
 33 31  1  0
 31 32  2  0
 32 29  1  0
 16 29  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098047

   4-[[5-(3H-benzimidazol-5-yl)-4-cyclopentyloxy-7H-pyrrolo[2,3-d]pyrimidin-2-yl]amino]-3-methoxy-N-methylbenzamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 497.56

Molecular Weight (Monoisotopic): 497.2175

AlogP: 4.93

#Rotatable Bonds: 7

Polar Surface Area: 129.84

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.51

CX Basic pKa: 5.68

CX LogP: 4.28

CX LogD: 4.27

Aromatic Rings: 5

Heavy Atoms: 37

QED Weighted: 0.25

Np Likeness Score: -0.79

References

1. Riggs JR, Nagy M, Elsner J, Erdman P, Cashion D, Robinson D, Harris R, Huang D, Tehrani L, Deyanat-Yazdi G, Narla RK, Peng X, Tran T, Barnes L, Miller T, Katz J, Tang Y, Chen M, Moghaddam MF, Bahmanyar S, Pagarigan B, Delker S, LeBrun L, Chamberlain PP, Calabrese A, Canan SS, Leftheris K, Zhu D, Boylan JF..  (2017)  The Discovery of a Dual TTK Protein Kinase/CDC2-Like Kinase (CLK2) Inhibitor for the Treatment of Triple Negative Breast Cancer Initiated from a Phenotypic Screen.,  60  (21): [PMID:28991472] [10.1021/acs.jmedchem.7b01223]

Source

Source(1):

• Scientific Literature