2-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]-6-methyl-8-phenylimidazo[1,2-a]pyridine

ID: ALA208274

PubChem CID: 11697270

Max Phase: Preclinical

Molecular Formula: C26H28N4O

Molecular Weight: 412.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(Cc2cn3cc(C)cc(-c4ccccc4)c3n2)CC1

Standard InChI:  InChI=1S/C26H28N4O/c1-20-16-23(21-8-4-3-5-9-21)26-27-22(19-30(26)17-20)18-28-12-14-29(15-13-28)24-10-6-7-11-25(24)31-2/h3-11,16-17,19H,12-15,18H2,1-2H3

Standard InChI Key:  LNEZIIGVFFLLQU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   12.7829    4.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7829    3.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4967    3.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4967    4.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2149    4.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2149    3.4969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    3.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4918    3.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0040    4.5831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3159    3.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7280    3.1980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3100    2.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7185    1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5430    1.7682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9572    2.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5470    3.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9523    1.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5344    0.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9430   -0.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7680   -0.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1826    0.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7715    1.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0692    3.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1839    1.7657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0080    1.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4955    5.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2122    5.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2115    6.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4967    7.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7811    6.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7854    5.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  6  7  1  0
 14 17  1  0
  7  8  2  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  9  5  2  0
 19 20  2  0
  5  4  1  0
 20 21  1  0
  8 10  1  0
 21 22  2  0
 22 17  1  0
  5  6  1  0
  2 23  1  0
 10 11  1  0
 22 24  1  0
 11 12  1  0
 24 25  1  0
  4 26  1  0
  1  2  1  0
 26 27  2  0
  1  4  2  0
 27 28  1  0
  2  3  2  0
 28 29  2  0
  3  6  1  0
 29 30  1  0
 11 16  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA208274

   2-[4-(2-Methoxyphenyl)piperazin-1-ylmethyl]-6-methyl-8-phenylimidazo[1,2-a]pyridine

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: 412.54

Molecular Weight (Monoisotopic): 412.2263

AlogP: 4.64

#Rotatable Bonds: 5

Polar Surface Area: 33.01

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.53

CX LogP: 4.52

CX LogD: 4.47

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -1.39

References

1. Enguehard-Gueiffier C, Hübner H, El Hakmaoui A, Allouchi H, Gmeiner P, Argiolas A, Melis MR, Gueiffier A..  (2006)  2-[(4-phenylpiperazin-1-yl)methyl]imidazo(di)azines as selective D4-ligands. Induction of penile erection by 2-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]imidazo[1,2-a]pyridine (PIP3EA), a potent and selective D4 partial agonist.,  49  (13): [PMID:16789750] [10.1021/jm060166w]

Source

Source(1):

• Scientific Literature