1-[1-(1-Phenyl-1H-pyrrol-3-ylmethyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one

ID: ALA146557

PubChem CID: 10761828

Max Phase: Preclinical

Molecular Formula: C23H24N4O

Molecular Weight: 372.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1nc2ccccc2n1C1CCN(Cc2ccn(-c3ccccc3)c2)CC1

Standard InChI:  InChI=1S/C23H24N4O/c28-23-24-21-8-4-5-9-22(21)27(23)20-11-13-25(14-12-20)16-18-10-15-26(17-18)19-6-2-1-3-7-19/h1-10,15,17,20H,11-14,16H2,(H,24,28)

Standard InChI Key:  DZKGMYCNIICGIS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    7.1917   -3.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -3.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -4.6750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -0.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5250   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0500   -2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -1.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8042   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -5.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -5.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4750   -5.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  7  1  0
  5  2  1  0
  6 16  1  0
  7  6  2  0
  8  3  1  0
  9 11  2  0
 10  2  1  0
 11  6  1  0
 12 19  1  0
 13  1  1  0
 14 10  1  0
 15 10  1  0
 16 12  1  0
 17  4  1  0
 18 14  1  0
 19 15  1  0
 20  5  2  0
 21  8  2  0
 22 17  2  0
 23 17  1  0
 24 20  1  0
 25 21  1  0
 26 22  1  0
 27 23  2  0
 28 27  1  0
  8  5  1  0
 24 25  2  0
 12 18  1  0
  9  4  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA146557

   1-[1-(1-Phenyl-1H-pyrrol-3-ylmethyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one

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: 372.47

Molecular Weight (Monoisotopic): 372.1950

AlogP: 4.37

#Rotatable Bonds: 4

Polar Surface Area: 46.22

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.66

CX Basic pKa: 8.42

CX LogP: 4.58

CX LogD: 3.52

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.35

References

1. 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