1-(2-Methoxy-phenyl)-4-(1-phenyl-1H-pyrrol-3-ylmethyl)-piperazine

ID: ALA28321

PubChem CID: 10450375

Max Phase: Preclinical

Molecular Formula: C22H25N3O

Molecular Weight: 347.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(Cc2ccn(-c3ccccc3)c2)CC1

Standard InChI:  InChI=1S/C22H25N3O/c1-26-22-10-6-5-9-21(22)24-15-13-23(14-16-24)17-19-11-12-25(18-19)20-7-3-2-4-8-20/h2-12,18H,13-17H2,1H3

Standard InChI Key:  UPXJKNQVKALXKP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.8292   -0.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625   -2.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -2.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5500   -2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -0.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0250   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -0.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8500   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875    0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2292   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  1  1  0
  4 12  1  0
  5  1  1  0
  6  4  1  0
  7  5  2  0
  8  9  1  0
  9  2  1  0
 10  1  1  0
 11 14  1  0
 12 15  1  0
 13  6  1  0
 14  8  1  0
 15  8  1  0
 16 13  1  0
 17  6  2  0
 18 10  2  0
 19 10  1  0
 20 13  2  0
 21 16  1  0
 22 17  1  0
 23 18  1  0
 24 19  2  0
 25 22  2  0
 26 24  1  0
  2  7  1  0
 23 26  2  0
 11  4  1  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA28321

   1-(2-Methoxy-phenyl)-4-(1-phenyl-1H-pyrrol-3-ylmethyl)-piperazine

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: 347.46

Molecular Weight (Monoisotopic): 347.1998

AlogP: 3.81

#Rotatable Bonds: 5

Polar Surface Area: 20.64

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.38

CX LogP: 4.46

CX LogD: 4.17

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -1.39

References

1. Perrone R, Berardi F, Colabufo NA, Leopoldo M, Tortorella V.  (1997)  1-(2-METHOXYPHENYL)-4-ALKYLPIPERAZINES: EFFECT OF THE N-4 SUBSTITUENT ON THE AFFINITY AND SELECTIVITY FOR DOPAMINE D4 RECEPTOR,  7  (10): [10.1016/S0960-894X(97)00218-7]

2. Perrone R, Berardi F, Colabufo NA, Leopoldo M, Tortorella V..  (1998)  N-[2-[4-(4-Chlorophenyl)piperazin-1-yl]ethyl]-3-methoxybenzamide: a potent and selective dopamine D4 ligand.,  41  (24): [PMID:9822559] [10.1021/jm981041x]

3. Thurkauf A, Yuan J, Chen X, Wasley JW, Meade R, Woodruff KH, Huston K, Ross PC..  (1995)  1-Phenyl-3-(aminomethyl)pyrroles as potential antipsychotic agents. Synthesis and dopamine receptor binding.,  38  (25): [PMID:8523409] [10.1021/jm00025a013]

Source

Source(1):

• Scientific Literature