US9181249, 137

ID: ALA3975542

PubChem CID: 118159125

Max Phase: Preclinical

Molecular Formula: C24H32F2N6O

Molecular Weight: 458.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)N1CCc2nc(N3CCN(Cc4ccc(F)cc4F)CC3)c(NC(C)C)nc2C1

Standard InChI:  InChI=1S/C24H32F2N6O/c1-4-22(33)32-8-7-20-21(15-32)28-23(27-16(2)3)24(29-20)31-11-9-30(10-12-31)14-17-5-6-18(25)13-19(17)26/h5-6,13,16H,4,7-12,14-15H2,1-3H3,(H,27,28)

Standard InChI Key:  RASASWOICGGBDJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    3.6331   -3.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1968    1.5003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995    3.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7974    2.9963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0999    3.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3974    2.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3898    1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6851    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9879    1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0241    0.8692    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9955    2.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7002    3.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7063    4.9309    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7950    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4948    0.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1953   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2312   -3.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1529   -3.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 16  1  0
 22 23  1  0
 14 24  1  0
 24 25  1  0
 25 11  1  0
 10 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 26 31  1  0
 31 32  2  0
 32  8  1  0
 32 33  1  0
 33  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3975542

   1-(2-(4-(2,4-difluorobenzyl)piperazin-1-yl)-3-(isopropylamino)-7,8-dihydropyrido[3,4-b]pyrazin-6(5H)-yl)propan-1-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: 458.56

Molecular Weight (Monoisotopic): 458.2606

AlogP: 3.19

#Rotatable Bonds: 6

Polar Surface Area: 64.60

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.97

CX LogP: 2.96

CX LogD: 2.94

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.72

Np Likeness Score: -1.82

References

1.  (2015)  Substituted pyrido[3,4-b]pyrazines as GPR6 modulators, 

2.  (2018)  Tetrahydropyridopyrazines modulators of gpr6, 

3.  (2016)  Tetrahydropyridopyrazines modulators of gpr6, 

Source

Source(2):

• BindingDB Database
• Patent Bioactivity Data