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

ID: ALA3735679

PubChem CID: 127036695

Max Phase: Preclinical

Molecular Formula: C22H25N5O2

Molecular Weight: 391.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCN(C(=O)c2cccc(-c3cc(-c4ccc(C)o4)nc(N)n3)c2)CC1

Standard InChI:  InChI=1S/C22H25N5O2/c1-3-26-9-11-27(12-10-26)21(28)17-6-4-5-16(13-17)18-14-19(25-22(23)24-18)20-8-7-15(2)29-20/h4-8,13-14H,3,9-12H2,1-2H3,(H2,23,24,25)

Standard InChI Key:  UQWBHMRNMCLLLN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    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
   -1.3092    5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    5.2404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9021    3.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6005    2.9949    0.0000 C   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
   -5.2112    5.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2474    5.3786    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
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  1  0
  9 22  1  0
 25 27  1  0
 19 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3735679

   ---

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: 391.48

Molecular Weight (Monoisotopic): 391.2008

AlogP: 3.07

#Rotatable Bonds: 4

Polar Surface Area: 88.49

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.08

CX LogP: 2.73

CX LogD: 2.56

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.74

Np Likeness Score: -1.60

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