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

ID: ALA3754358

PubChem CID: 127036831

Max Phase: Preclinical

Molecular Formula: C21H20N4O2

Molecular Weight: 360.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(-c2ccccc2)cc(-c2cccc(OC(=O)N3CCCC3)c2)n1

Standard InChI:  InChI=1S/C21H20N4O2/c22-20-23-18(15-7-2-1-3-8-15)14-19(24-20)16-9-6-10-17(13-16)27-21(26)25-11-4-5-12-25/h1-3,6-10,13-14H,4-5,11-12H2,(H2,22,23,24)

Standard InChI Key:  GACMIYCVRUMFFL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    3.8933   -3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   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
   -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
    1.2954    5.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978    3.7529    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
   -1.3002    3.7488    0.0000 C   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
   -0.0048    6.0009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035    5.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9027    5.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2017    5.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2017    7.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9027    8.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6036    7.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3337    5.8546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4984   -5.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2484   -4.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2447   -3.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  2  4  1  0
  1  2  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 15 17  1  0
 11 23  1  0
  7 13  1  0
  4  5  1  0
  1 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3754358

   ---

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: 360.42

Molecular Weight (Monoisotopic): 360.1586

AlogP: 3.99

#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: 4.09

CX LogD: 4.09

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -0.98

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]

Source

Source(1):

• Scientific Literature