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

ID: ALA549638

PubChem CID: 45270861

Max Phase: Preclinical

Molecular Formula: C20H24FN5

Molecular Weight: 353.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H24FN5/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:  RTYGYVMXTLAVMS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    8.4784   -4.1458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4784   -4.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7639   -5.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7639   -3.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0495   -4.1458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0495   -4.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2648   -5.2258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7799   -4.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2648   -3.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9549   -4.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0099   -3.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2029   -2.9348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9480   -2.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1410   -1.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5890   -2.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8439   -3.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6509   -3.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820   -2.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2300   -3.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4230   -2.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1681   -2.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7201   -1.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5271   -1.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1929   -5.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7639   -2.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611   -1.9056    0.0000 F   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:

   

   ALA549638

   3-{[4-(4-Fluorophenyl)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: 353.44

Molecular Weight (Monoisotopic): 353.2016

AlogP: 3.12

#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: 6.96

CX LogP: 1.69

CX LogD: 1.55

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -2.00

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