6-[3-(2-Methyl-pyridin-4-yl)-propoxy]-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one Oxime

ID: ALA4092850

PubChem CID: 137652776

Max Phase: Preclinical

Molecular Formula: C25H22N4O3

Molecular Weight: 426.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(CCCOc2ccc3oc(-c4cc5cccn5cn4)c/c(=N\O)c3c2)ccn1

Standard InChI:  InChI=1S/C25H22N4O3/c1-17-12-18(8-9-26-17)4-3-11-31-20-6-7-24-21(14-20)22(28-30)15-25(32-24)23-13-19-5-2-10-29(19)16-27-23/h2,5-10,12-16,30H,3-4,11H2,1H3/b28-22+

Standard InChI Key:  VSOCOTWHUMRARV-XAYXJRQQSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    7.0685   -5.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0674   -6.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7754   -7.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7736   -5.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4823   -5.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4811   -6.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1912   -7.1637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1935   -5.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9082   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9095   -6.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1936   -4.6961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9013   -4.2876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6243   -7.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6273   -7.9793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3412   -8.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3267   -6.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0386   -7.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0489   -7.9637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8358   -8.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3119   -7.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8191   -6.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3607   -5.5224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6531   -5.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9453   -5.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2377   -5.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5299   -5.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5335   -4.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266   -4.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -4.7061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208   -5.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284   -5.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268   -3.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
 10  9  2  0
  8 11  2  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 15 18  1  0
 17 16  1  0
 16 13  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  2  0
  1 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092850

   ---

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: 426.48

Molecular Weight (Monoisotopic): 426.1692

AlogP: 4.75

#Rotatable Bonds: 6

Polar Surface Area: 85.15

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.46

CX Basic pKa: 6.38

CX LogP: 2.78

CX LogD: 2.68

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.24

Np Likeness Score: -0.59

References

1. Charvin D, Pomel V, Ortiz M, Frauli M, Scheffler S, Steinberg E, Baron L, Deshons L, Rudigier R, Thiarc D, Morice C, Manteau B, Mayer S, Graham D, Giethlen B, Brugger N, Hédou G, Conquet F, Schann S..  (2017)  Discovery, Structure-Activity Relationship, and Antiparkinsonian Effect of a Potent and Brain-Penetrant Chemical Series of Positive Allosteric Modulators of Metabotropic Glutamate Receptor 4.,  60  (20): [PMID:28902994] [10.1021/acs.jmedchem.7b00991]

Source

Source(1):

• Scientific Literature