(S)-5,5-dimethyl-7-(1-phenylethyl)-2-(pyridin-3-ylamino)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

ID: ALA3884884

PubChem CID: 70942743

Max Phase: Preclinical

Molecular Formula: C21H21N5O

Molecular Weight: 359.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](c1ccccc1)N1C(=O)C(C)(C)c2cnc(Nc3cccnc3)nc21

Standard InChI:  InChI=1S/C21H21N5O/c1-14(15-8-5-4-6-9-15)26-18-17(21(2,3)19(26)27)13-23-20(25-18)24-16-10-7-11-22-12-16/h4-14H,1-3H3,(H,23,24,25)/t14-/m0/s1

Standard InChI Key:  LNCUDNJUDSTTIM-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    1.1061   -9.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188   -9.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013   -9.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271  -10.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8351  -10.9233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448  -10.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5420   -9.6912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1282   -9.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8355   -9.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6644   -8.4859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514   -8.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116   -7.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0117   -8.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428   -7.6939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2531  -10.9214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9602  -10.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6652  -10.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3718  -10.5106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3710   -9.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6576   -9.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9540   -9.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592   -7.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2613   -8.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0606   -8.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6096   -8.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3537   -7.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550   -7.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  8  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  9  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  2  8  1  0
 12 13  1  0
 10 12  1  0
 11 14  2  0
  6 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
 12 22  1  1
 13 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3884884

   5,5-dimethyl-7-[(1S)-1-phenylethyl]-2-(pyridin-3-ylamino)pyrrolo[2,3-d]pyrimidin-6-one

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: 359.43

Molecular Weight (Monoisotopic): 359.1746

AlogP: 4.00

#Rotatable Bonds: 4

Polar Surface Area: 71.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.43

CX Basic pKa: 5.27

CX LogP: 3.75

CX LogD: 3.75

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -1.02

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