US9181249, 136

ID: ALA3946230

PubChem CID: 118159178

Max Phase: Preclinical

Molecular Formula: C22H30F2N6O2S

Molecular Weight: 480.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Nc1nc2c(nc1N1CCN(Cc3ccc(F)cc3F)CC1)CCN(S(C)(=O)=O)C2

Standard InChI:  InChI=1S/C22H30F2N6O2S/c1-15(2)25-21-22(27-19-6-7-30(33(3,31)32)14-20(19)26-21)29-10-8-28(9-11-29)13-16-4-5-17(23)12-18(16)24/h4-5,12,15H,6-11,13-14H2,1-3H3,(H,25,26)

Standard InChI Key:  LLDFGRFJUUBZCG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    4.9395   -1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969    0.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    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
    1.2990    0.7500    0.0000 N   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
    0.0000    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    3.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    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
   -1.2990   -0.7500    0.0000 N   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
    0.0000   -3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978   -3.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2955   -5.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048   -6.0009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0102   -7.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3123   -8.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076   -7.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9104   -8.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180   -9.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9602  -10.3298    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6227  -10.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199   -9.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2837  -10.3535    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3026   -5.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3002   -3.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    5.2508    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602    5.8515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3385    5.8505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997    6.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  7  2  0
 12 13  1  0
 13 14  2  0
 14  5  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 20  1  0
 26 27  1  0
 18 28  1  0
 28 29  1  0
 29 15  1  0
  9 30  1  0
 30 31  2  0
 30 32  2  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3946230

   2-(4-(2,4-difluorobenzyl)piperazin-1-yl)-N-isopropyl-6-(methylsulfonyl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine

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: 480.59

Molecular Weight (Monoisotopic): 480.2119

AlogP: 2.21

#Rotatable Bonds: 6

Polar Surface Area: 81.67

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.97

CX LogP: 1.75

CX LogD: 1.74

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.68

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