US9181249, 138

ID: ALA3958294

PubChem CID: 118159271

Max Phase: Preclinical

Molecular Formula: C21H34N6O3

Molecular Weight: 418.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCc2nc(N3CCN(C(=O)OC(C)(C)C)CC3)c(NC(C)C)nc2C1

Standard InChI:  InChI=1S/C21H34N6O3/c1-14(2)22-18-19(24-16-7-8-27(15(3)28)13-17(16)23-18)25-9-11-26(12-10-25)20(29)30-21(4,5)6/h14H,7-13H2,1-6H3,(H,22,23)

Standard InChI Key:  CJEZYFCOYOMTCD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  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
    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
    0.0102   -7.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270   -8.1051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3123   -8.2482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177   -9.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588  -10.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3215  -10.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805  -10.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    5.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3422    5.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640    5.8526    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 15  1  0
 18 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
  9 28  1  0
 28 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3958294

   Tert-butyl 4-(6-acetyl-3-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-yl)piperazine-1-carboxylate

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: 418.54

Molecular Weight (Monoisotopic): 418.2692

AlogP: 2.26

#Rotatable Bonds: 3

Polar Surface Area: 90.90

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.41

CX LogP: 1.15

CX LogD: 1.15

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.81

Np Likeness Score: -1.27

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