1-((1S,5R)-6-(6-(6-amino-5-(difluoromethoxy)pyridin-3-yl)-2-ethylpyrimidin-4-yl)-3-azabicyclo[3.1.0]hexan-3-yl)propan-2-ol

ID: ALA3728116

PubChem CID: 117688780

Max Phase: Preclinical

Molecular Formula: C20H25F2N5O2

Molecular Weight: 405.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nc(-c2cnc(N)c(OC(F)F)c2)cc([C@H]2[C@@H]3CN(CC(C)O)C[C@@H]32)n1

Standard InChI:  InChI=1S/C20H25F2N5O2/c1-3-17-25-14(11-4-16(29-20(21)22)19(23)24-6-11)5-15(26-17)18-12-8-27(7-10(2)28)9-13(12)18/h4-6,10,12-13,18,20,28H,3,7-9H2,1-2H3,(H2,23,24)/t10?,12-,13+,18+

Standard InChI Key:  VDFSZXGVPFLXPY-HHTXZJQKSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    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
   -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
    0.0000   -2.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0008    0.0000 C   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
    1.2954    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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.4978    0.0000 O   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
   -4.9395   -1.3434    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969    0.4545    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051    5.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6425    5.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939    6.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6035    7.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865    5.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9746    6.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9673    7.4004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    8.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2570    8.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2356    9.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2658   10.2867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1878   10.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7741    6.3440    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4697    6.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  3  8  1  0
  5 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 12 18  1  0
 18 19  1  0
 22 20  1  0
 20 21  1  0
 20 10  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 22 30  1  6
 21 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3728116

   1-[(1S,5R)-6-[6-[6-amino-5-(difluoromethoxy)pyridin-3-yl]-2-ethylpyrimidin-4-yl]-3-azabicyclo[3.1.0]hexan-3-yl]propan-2-ol

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: 405.45

Molecular Weight (Monoisotopic): 405.1976

AlogP: 2.31

#Rotatable Bonds: 7

Polar Surface Area: 97.39

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.99

CX LogP: 2.26

CX LogD: 0.67

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.73

Np Likeness Score: -0.91

References

1.  (2014)  Biheteroaryl compounds and uses thereof, 

2.  (2014)  Biheteroaryl compounds and uses thereof, 

Source

Source(1):

• Patent Bioactivity Data