(R)-7-(2,2-difluoro-1-phenylethyl)-5,5-dimethyl-2-(phenylamino)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

ID: ALA3885257

PubChem CID: 134130107

Max Phase: Preclinical

Molecular Formula: C22H20F2N4O

Molecular Weight: 394.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C(=O)N([C@H](c2ccccc2)C(F)F)c2nc(Nc3ccccc3)ncc21

Standard InChI:  InChI=1S/C22H20F2N4O/c1-22(2)16-13-25-21(26-15-11-7-4-8-12-15)27-19(16)28(20(22)29)17(18(23)24)14-9-5-3-6-10-14/h3-13,17-18H,1-2H3,(H,25,26,27)/t17-/m1/s1

Standard InChI Key:  HUHRXBBSMSZINZ-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

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    4.1396  -19.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0347  -21.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474  -20.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6299  -20.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0557  -22.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638  -22.6735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4734  -22.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706  -21.4414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0569  -21.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7641  -21.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5931  -20.2361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7800  -20.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403  -19.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3714  -19.4441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1818  -22.6716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8888  -22.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5939  -22.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3004  -22.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2996  -21.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5863  -21.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8826  -21.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1899  -20.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9892  -20.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5382  -20.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2823  -19.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4837  -19.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8874  -18.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4344  -18.2406    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0881  -18.6775    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  9  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8 10  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  3  1  0
  3  9  1  0
  1 13  1  0
 11  1  1  0
 12 14  2  0
  7 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 13  1  0
  1 27  1  1
 27 28  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3885257

   ---

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: 394.43

Molecular Weight (Monoisotopic): 394.1605

AlogP: 4.85

#Rotatable Bonds: 5

Polar Surface Area: 58.12

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.07

CX Basic pKa: 0.73

CX LogP: 5.08

CX LogD: 5.08

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -0.80

References

1. Katz JD, Haidle A, Childers KK, Zabierek AA, Jewell JP, Hou Y, Altman MD, Szewczak A, Chen D, Harsch A, Hayashi M, Warren L, Hutton M, Nuthall H, Su HP, Munshi S, Stanton MG, Davies IW, Munoz B, Northrup A..  (2017)  Structure guided design of a series of selective pyrrolopyrimidinone MARK inhibitors.,  27  (1): [PMID:27816515] [10.1016/j.bmcl.2016.08.068]

Source

Source(1):

• Scientific Literature