4-(5-methylfuran-2-yl)-6-[3-(pyrrolidine-1-carbonyl)phenyl]pyrimidin-2-amine

ID: ALA3735439

PubChem CID: 127036697

Max Phase: Preclinical

Molecular Formula: C20H20N4O2

Molecular Weight: 348.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2cc(-c3cccc(C(=O)N4CCCC4)c3)nc(N)n2)o1

Standard InChI:  InChI=1S/C20H20N4O2/c1-13-7-8-18(26-13)17-12-16(22-20(21)23-17)14-5-4-6-15(11-14)19(25)24-9-2-3-10-24/h4-8,11-12H,2-3,9-10H2,1H3,(H2,21,22,23)

Standard InChI Key:  JYVLYFJUIUVRCK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
   -2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969   -1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1945   -3.0046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -3.0004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924   -4.9525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351    3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4978   -0.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6404    0.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1086    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8544   -0.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8472   -1.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0475   -0.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470    5.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153    5.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607    4.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6532    3.1236    0.0000 C   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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  5  7  1  0
 11 13  1  0
  3 14  1  0
 14 15  2  0
 14 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  1  0
  9 17  1  0
 20 22  1  0
 16 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3735439

   ---

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: 348.41

Molecular Weight (Monoisotopic): 348.1586

AlogP: 3.53

#Rotatable Bonds: 3

Polar Surface Area: 85.25

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.90

CX LogP: 2.93

CX LogD: 2.93

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: -1.43

References

1. Robinson SJ, Petzer JP, Terre'Blanche G, Petzer A, van der Walt MM, Bergh JJ, Lourens AC..  (2015)  2-Aminopyrimidines as dual adenosine A1/A2A antagonists.,  104  [PMID:26462195] [10.1016/j.ejmech.2015.09.035]

Source

Source(1):

• Scientific Literature