(R)-2-(4-cyanophenyl)-N-(4-(7-(1-hydroxypropan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)pyridin-2-yl)acetamide

ID: ALA4793692

PubChem CID: 162673273

Max Phase: Preclinical

Molecular Formula: C24H20N6O3

Molecular Weight: 440.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H](CO)n1cc(C(=O)c2ccnc(NC(=O)Cc3ccc(C#N)cc3)c2)c2cncnc21

Standard InChI:  InChI=1S/C24H20N6O3/c1-15(13-31)30-12-20(19-11-26-14-28-24(19)30)23(33)18-6-7-27-21(9-18)29-22(32)8-16-2-4-17(10-25)5-3-16/h2-7,9,11-12,14-15,31H,8,13H2,1H3,(H,27,29,32)/t15-/m1/s1

Standard InChI Key:  ATGFOXPRMFMNMG-OAHLLOKOSA-N

Molfile:  

 
     RDKit          2D

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   13.3170  -12.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6822  -14.1844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3123  -13.8192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7340  -13.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5814  -12.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3688  -11.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9471  -12.4534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5808  -13.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4101  -13.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375  -12.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9461  -12.0026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7633  -12.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7633  -13.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3111  -11.3920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9702  -12.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0584  -11.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3631  -10.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1403  -10.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7468  -10.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7566  -10.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1044  -12.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3134  -11.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1049  -11.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6833  -12.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4701  -12.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6827  -13.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4706  -11.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2621  -11.7611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
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  6  7  2  0
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  9 10  1  0
  5 10  2  0
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 15 19  1  0
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 22 23  1  0
 23 24  1  1
 22 25  1  0
 19 23  1  0
  7 11  1  0
  4  5  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 26 31  2  0
 32 33  3  0
 29 32  1  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4793692

   ---

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: 440.46

Molecular Weight (Monoisotopic): 440.1597

AlogP: 2.66

#Rotatable Bonds: 7

Polar Surface Area: 133.79

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.93

CX Basic pKa: 3.76

CX LogP: 2.23

CX LogD: 2.23

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: -1.32

References

1. Skerratt SE,Andrews M,Bagal SK,Bilsland J,Brown D,Bungay PJ,Cole S,Gibson KR,Jones R,Morao I,Nedderman A,Omoto K,Robinson C,Ryckmans T,Skinner K,Stupple P,Waldron G.  (2016)  The Discovery of a Potent, Selective, and Peripherally Restricted Pan-Trk Inhibitor (PF-06273340) for the Treatment of Pain.,  59  (22): [PMID:27766865] [10.1021/acs.jmedchem.6b00850]

Source

Source(1):

• Scientific Literature