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

ID: ALA210283

PubChem CID: 11631892

Max Phase: Preclinical

Molecular Formula: C21H23N5O

Molecular Weight: 361.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(Cc2cn3cc(C)cc(C#N)c3n2)CC1

Standard InChI:  InChI=1S/C21H23N5O/c1-16-11-17(12-22)21-23-18(15-26(21)13-16)14-24-7-9-25(10-8-24)19-5-3-4-6-20(19)27-2/h3-6,11,13,15H,7-10,14H2,1-2H3

Standard InChI Key:  VXHLHYPOHKQMNB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.4945  -23.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945  -24.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2084  -25.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2084  -23.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9270  -23.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9269  -24.7143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7163  -24.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042  -24.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7163  -23.6279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0286  -24.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4408  -25.0133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0227  -25.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4313  -26.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2561  -26.4436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6705  -25.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2601  -25.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6656  -27.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2475  -27.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6563  -28.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4815  -28.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8964  -27.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4852  -27.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7805  -25.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8977  -26.4461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7221  -26.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2072  -22.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2061  -21.8216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0
  2  3  2  0
  3  6  1  0
 11 16  1  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
  1  2  1  0
 26 27  3  0
  4 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA210283

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

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: 361.45

Molecular Weight (Monoisotopic): 361.1903

AlogP: 2.85

#Rotatable Bonds: 4

Polar Surface Area: 56.80

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.91

CX LogP: 2.73

CX LogD: 2.72

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -1.89

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