US9181249, 152

ID: ALA3972078

PubChem CID: 118159205

Max Phase: Preclinical

Molecular Formula: C23H29F2N5O3S

Molecular Weight: 493.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)N1CCc2nc(N3CCC(Oc4ccc(F)cc4F)CC3)c(NC3CCC3)nc2C1

Standard InChI:  InChI=1S/C23H29F2N5O3S/c1-34(31,32)30-12-9-19-20(14-30)27-22(26-16-3-2-4-16)23(28-19)29-10-7-17(8-11-29)33-21-6-5-15(24)13-18(21)25/h5-6,13,16-17H,2-4,7-12,14H2,1H3,(H,26,27)

Standard InChI Key:  RJZHGBONFGIONP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    2.5984   -2.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6384   -0.9011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6377   -2.1009    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
   -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  2  0
  2  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 11  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 18  1  0
 24 25  1  0
 10 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 28  1  0
 26 32  1  0
 32 33  2  0
 33  8  1  0
 33 34  1  0
 34  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3972078

   N-cyclobutyl-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-6-methylsulfonyl-7,8-dihydro-5H-pyrido[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: 493.58

Molecular Weight (Monoisotopic): 493.1959

AlogP: 3.08

#Rotatable Bonds: 6

Polar Surface Area: 87.66

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.39

CX LogP: 1.97

CX LogD: 1.97

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.66

Np Likeness Score: -1.37

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