3-{[4-(2-Methoxyphenyl)piperazin-1-yl]methyl}-5,7-dimethylimidazo[1,2-c]pyrimidine

ID: ALA563109

PubChem CID: 45272580

Max Phase: Preclinical

Molecular Formula: C20H25N5O

Molecular Weight: 351.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(Cc2cnc3cc(C)nc(C)n23)CC1

Standard InChI:  InChI=1S/C20H25N5O/c1-15-12-20-21-13-17(25(20)16(2)22-15)14-23-8-10-24(11-9-23)18-6-4-5-7-19(18)26-3/h4-7,12-13H,8-11,14H2,1-3H3

Standard InChI Key:  VGIPYYQGXWSQEJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.8059   -7.2029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8059   -8.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -8.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -6.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -7.2029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -8.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -8.2828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1074   -7.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -6.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3374   -6.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4696   -5.9918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7246   -5.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -5.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836   -5.6487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -6.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0217   -6.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905   -5.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426   -6.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2495   -5.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5045   -5.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9524   -4.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -4.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5203   -8.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -5.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5934   -4.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865   -4.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  1  0
  1  2  1  0
  5  4  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  6  7  2  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  2  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
 22 17  1  0
 14 17  1  0
  5  6  1  0
  2 23  1  0
 10 11  1  0
  4 24  1  0
 11 12  1  0
 22 25  1  0
  2  3  2  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA563109

   3-{[4-(2-Methoxyphenyl)piperazin-1-yl]methyl}-5,7-dimethylimidazo[1,2-c]pyrimidine

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: 351.45

Molecular Weight (Monoisotopic): 351.2059

AlogP: 2.68

#Rotatable Bonds: 4

Polar Surface Area: 45.90

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.56

CX LogP: 1.26

CX LogD: 1.20

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -1.71

References

1. Linz S, Müller J, Hübner H, Gmeiner P, Troschütz R..  (2009)  Design, synthesis and dopamine D4 receptor binding activities of new N-heteroaromatic 5/6-ring Mannich bases.,  17  (13): [PMID:19481941] [10.1016/j.bmc.2009.05.015]

Source

Source(1):

• Scientific Literature