3-(2-amino-6-phenylpyrimidin-4-yl)phenyl piperidine-1-carboxylate

ID: ALA3753339

PubChem CID: 127035994

Max Phase: Preclinical

Molecular Formula: C22H22N4O2

Molecular Weight: 374.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(-c2ccccc2)cc(-c2cccc(OC(=O)N3CCCCC3)c2)n1

Standard InChI:  InChI=1S/C22H22N4O2/c23-21-24-19(16-8-3-1-4-9-16)15-20(25-21)17-10-7-11-18(14-17)28-22(27)26-12-5-2-6-13-26/h1,3-4,7-11,14-15H,2,5-6,12-13H2,(H2,23,24,25)

Standard InChI Key:  YRHUKOHIJREPRH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  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
    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
    2.5951   -3.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8934   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -6.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925   -3.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969   -9.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -8.2599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -7.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4926   -8.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4949   -9.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1971  -10.5079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7958  -10.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0950   -9.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3940  -10.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3939  -12.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0949  -12.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7959  -12.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586  -10.3616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  7  9  1  0
  1  7  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 20 22  1  0
 16 28  1  0
 12 18  1  0
  9 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3753339

   ---

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: 374.44

Molecular Weight (Monoisotopic): 374.1743

AlogP: 4.38

#Rotatable Bonds: 3

Polar Surface Area: 81.34

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.83

CX LogP: 4.54

CX LogD: 4.54

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.74

Np Likeness Score: -0.96

References

1. Robinson SJ, Petzer JP, Rousseau AL, Terre'Blanche G, Petzer A, Lourens AC..  (2016)  Carbamate substituted 2-amino-4,6-diphenylpyrimidines as adenosine receptor antagonists.,  26  (3): [PMID:26776359] [10.1016/j.bmcl.2016.01.004]

2. Saini A, Patel R, Gaba S, Singh G, Gupta GD, Monga V..  (2022)  Adenosine receptor antagonists: Recent advances and therapeutic perspective.,  227  [PMID:34695776] [10.1016/j.ejmech.2021.113907]

Source

Source(1):

• Scientific Literature