5-Benzyl-1-methyl-2-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

ID: ALA4103768

PubChem CID: 137658266

Max Phase: Preclinical

Molecular Formula: C24H27N5O2

Molecular Weight: 417.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(-c2ccnc(NC3CCOCC3)n2)cc2c1CCN(Cc1ccccc1)C2=O

Standard InChI:  InChI=1S/C24H27N5O2/c1-28-21-8-12-29(16-17-5-3-2-4-6-17)23(30)19(21)15-22(28)20-7-11-25-24(27-20)26-18-9-13-31-14-10-18/h2-7,11,15,18H,8-10,12-14,16H2,1H3,(H,25,26,27)

Standard InChI Key:  UQFPBBSPMHMAFE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   13.5391   -8.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8341   -8.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8341   -7.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5391   -7.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2482   -7.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2482   -8.3449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0569   -7.2730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0569   -8.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5768   -7.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5391   -9.5707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5338   -8.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3510   -8.6413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7596   -7.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3510   -7.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5338   -7.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1252   -7.9363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1252   -9.3504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0822  -10.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8994  -10.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3080   -9.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8994   -8.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0822   -8.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6736   -9.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8022   -6.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9531   -8.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6622   -8.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6622   -7.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3713   -7.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0804   -7.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0804   -8.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3713   -8.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  8  9  2  0
  7  9  1  0
  2  8  1  0
  3  7  1  0
  1 10  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 23  1  0
 17 20  1  0
 11 17  1  0
  9 13  1  0
  7 24  1  0
 25 26  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
  6 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103768

   ---

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: 417.51

Molecular Weight (Monoisotopic): 417.2165

AlogP: 3.27

#Rotatable Bonds: 5

Polar Surface Area: 72.28

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.86

CX LogP: 2.17

CX LogD: 2.17

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.69

Np Likeness Score: -1.02

References

1. Ward RA, Bethel P, Cook C, Davies E, Debreczeni JE, Fairley G, Feron L, Flemington V, Graham MA, Greenwood R, Griffin N, Hanson L, Hopcroft P, Howard TD, Hudson J, James M, Jones CD, Jones CR, Lamont S, Lewis R, Lindsay N, Roberts K, Simpson I, St-Gallay S, Swallow S, Tang J, Tonge M, Wang Z, Zhai B..  (2017)  Structure-Guided Discovery of Potent and Selective Inhibitors of ERK1/2 from a Modestly Active and Promiscuous Chemical Start Point.,  60  (8): [PMID:28376306] [10.1021/acs.jmedchem.7b00267]

Source

Source(1):

• Scientific Literature