US9181249, 150

ID: ALA3979765

PubChem CID: 118159189

Max Phase: Preclinical

Molecular Formula: C25H31F2N5O3

Molecular Weight: 487.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)N1CCc2nc(N3CCC(Oc4ccc(F)cc4F)CC3)c(N[C@H]3CCOC3)nc2C1

Standard InChI:  InChI=1S/C25H31F2N5O3/c1-2-23(33)32-11-7-20-21(14-32)29-24(28-17-8-12-34-15-17)25(30-20)31-9-5-18(6-10-31)35-22-4-3-16(26)13-19(22)27/h3-4,13,17-18H,2,5-12,14-15H2,1H3,(H,28,29)/t17-/m0/s1

Standard InChI Key:  JRJLPTCUEBFMPA-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  1  0  0  0  0  0999 V2000
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    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
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   -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
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  -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
   -6.4037   -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 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
 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:

   

   ALA3979765

   (S)-1-(2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-3-(tetrahydrofuran-3-ylamino)-7,8-dihydropyrido[3,4-b]pyrazin-6(5H)-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: 487.55

Molecular Weight (Monoisotopic): 487.2395

AlogP: 3.30

#Rotatable Bonds: 6

Polar Surface Area: 79.82

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.36

CX LogP: 2.17

CX LogD: 2.17

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.67

Np Likeness Score: -1.19

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