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

ID: ALA554692

PubChem CID: 45271691

Max Phase: Preclinical

Molecular Formula: C20H24ClN5

Molecular Weight: 369.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2nc(C)c(CN3CCN(c4ccc(Cl)cc4)CC3)n2c(C)n1

Standard InChI:  InChI=1S/C20H24ClN5/c1-14-12-20-23-15(2)19(26(20)16(3)22-14)13-24-8-10-25(11-9-24)18-6-4-17(21)5-7-18/h4-7,12H,8-11,13H2,1-3H3

Standard InChI Key:  AQHZNVAMLJSYRQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    7.6324   -0.3468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6324   -1.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9180   -1.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9180    0.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2035   -0.3468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2035   -1.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4189   -1.4267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9340   -0.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4189   -0.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090   -0.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1639    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570    0.8643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1020    1.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2951    1.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7430    1.2074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    0.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049    0.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361    1.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3840    0.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221    1.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8741    2.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    2.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3469   -1.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9180    0.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849    1.8935    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  6  1  0
  1  2  1  0
  5  4  1  0
  6  7  2  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  8  1  0
  8  9  2  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  1  2  0
 20 21  2  0
  8 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
  9 11  1  0
  2 24  1  0
  4 25  1  0
 11 12  1  0
 12 13  1  0
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA554692

   3-{[4-(4-Chlorophenyl)piperazin-1-yl]methyl}-2,5,7-trimethylimidazo[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: 369.90

Molecular Weight (Monoisotopic): 369.1720

AlogP: 3.63

#Rotatable Bonds: 3

Polar Surface Area: 36.67

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.00

CX LogP: 2.15

CX LogD: 2.01

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -1.91

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