US9181249, 155

ID: ALA3944212

PubChem CID: 118159364

Max Phase: Preclinical

Molecular Formula: C25H32F2N6O2

Molecular Weight: 486.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)N1CCc2nc(N3CCN(Cc4ccc(F)cc4F)CC3)c(N[C@H]3CCOC3)nc2C1

Standard InChI:  InChI=1S/C25H32F2N6O2/c1-2-23(34)33-7-5-21-22(15-33)29-24(28-19-6-12-35-16-19)25(30-21)32-10-8-31(9-11-32)14-17-3-4-18(26)13-20(17)27/h3-4,13,19H,2,5-12,14-16H2,1H3,(H,28,29)/t19-/m0/s1

Standard InChI Key:  IDGIOUPKISJVFS-IBGZPJMESA-N

Molfile:  

     RDKit          2D

 35 39  0  0  1  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
   -6.4037   -3.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9352   -5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4352   -5.2877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9766   -3.8595    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
 28 27  1  6
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 28  1  0
 26 33  1  0
 33 34  2  0
 34  8  1  0
 34 35  1  0
 35  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3944212

   1-[2-[4-[(2,4-difluorophenyl)methyl]piperazin-1-yl]-3-[[(3S)-oxolan-3-yl]amino]-7,8-dihydro-5H-pyrido[3,4-b]pyrazin-6-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: 486.57

Molecular Weight (Monoisotopic): 486.2555

AlogP: 2.57

#Rotatable Bonds: 6

Polar Surface Area: 73.83

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: 2.09

CX LogD: 2.07

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.67

Np Likeness Score: -1.61

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