(S)-2-(2-Methoxyethyl)-3-methyl-7-(5-methyl-2-((1-methyl-1H-pyrazol-5-yl)amino)pyrimidin-4-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one

ID: ALA4098608

PubChem CID: 122604219

Max Phase: Preclinical

Molecular Formula: C20H25N7O2

Molecular Weight: 395.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCN1C(=O)c2cc(-c3nc(Nc4ccnn4C)ncc3C)cn2C[C@@H]1C

Standard InChI:  InChI=1S/C20H25N7O2/c1-13-10-21-20(23-17-5-6-22-25(17)3)24-18(13)15-9-16-19(28)27(7-8-29-4)14(2)11-26(16)12-15/h5-6,9-10,12,14H,7-8,11H2,1-4H3,(H,21,23,24)/t14-/m0/s1

Standard InChI Key:  MLMCYOUMLZXVEE-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   13.1147   -7.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8306   -7.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1147   -8.5609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5422   -7.7359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5422   -8.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8306   -8.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3301   -7.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8453   -8.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3301   -8.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8306   -6.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7828   -8.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6078   -8.8602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0203   -8.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6078   -7.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7828   -7.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3703   -8.1484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3703   -9.5760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0606   -8.9064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2760   -9.1635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2760   -9.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0606  -10.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5453   -9.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3135   -8.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0203   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2581   -8.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2581   -7.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9739   -7.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9739   -8.5609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6857   -8.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  3  6  1  0
  7  8  1  0
  8  9  2  0
  3  9  1  0
  1  7  2  0
  2 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  2  0
 20 21  1  0
 21 22  2  0
 18 22  1  0
 18 23  1  0
 17 22  1  0
 11 17  1  0
 14 24  1  0
  8 13  1  0
  5 25  1  1
 26 27  1  0
 28 29  1  0
 27 28  1  0
  4 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098608

   ---

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: 395.47

Molecular Weight (Monoisotopic): 395.2070

AlogP: 2.22

#Rotatable Bonds: 6

Polar Surface Area: 90.10

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.78

CX Basic pKa: 3.05

CX LogP: 1.95

CX LogD: 1.95

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -1.42

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