US9181249, 151

ID: ALA3954223

PubChem CID: 118159309

Max Phase: Preclinical

Molecular Formula: C24H27F4N5O2

Molecular Weight: 493.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCc2nc(N3CCC(Oc4ccc(F)cc4F)CC3)c(NC3CC(F)(F)C3)nc2C1

Standard InChI:  InChI=1S/C24H27F4N5O2/c1-14(34)33-9-6-19-20(13-33)30-22(29-16-11-24(27,28)12-16)23(31-19)32-7-4-17(5-8-32)35-21-3-2-15(25)10-18(21)26/h2-3,10,16-17H,4-9,11-13H2,1H3,(H,29,30)

Standard InChI Key:  KCSNHUSEVYLGAW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
    3.6375   -0.9049    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
    2.5956   -2.7031    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 C   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
   -9.0999    3.7419    0.0000 O   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
   -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
   -6.2503   -4.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1859   -5.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2251   -5.6737    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1427   -5.6666    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1290   -4.0092    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  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  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 10  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 17  1  0
 23 24  1  0
  9 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 32 27  1  0
 25 33  1  0
 33 34  2  0
 34  7  1  0
 34 35  1  0
 35  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3954223

   1-(3-((3,3-difluorocyclobutyl)amino)-2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-7,8-dihydropyrido[3,4-b]pyrazin-6(5H)-yl)ethan-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: 493.51

Molecular Weight (Monoisotopic): 493.2101

AlogP: 3.92

#Rotatable Bonds: 5

Polar Surface Area: 70.59

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.39

CX LogP: 2.69

CX LogD: 2.69

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.64

Np Likeness Score: -1.12

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