4-(4-Chloro-phenyl)-1-(1-phenyl-1H-pyrrol-3-ylmethyl)-piperidin-4-ol

ID: ALA147003

PubChem CID: 10642702

Max Phase: Preclinical

Molecular Formula: C22H23ClN2O

Molecular Weight: 366.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC1(c2ccc(Cl)cc2)CCN(Cc2ccn(-c3ccccc3)c2)CC1

Standard InChI:  InChI=1S/C22H23ClN2O/c23-20-8-6-19(7-9-20)22(26)11-14-24(15-12-22)16-18-10-13-25(17-18)21-4-2-1-3-5-21/h1-10,13,17,26H,11-12,14-16H2

Standard InChI Key:  VDEUXXAFBFOEGY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.9167   -0.8625    0.0000 N   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
    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
    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
    5.8292   -3.7167    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
    6.2000   -1.5000    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
    5.0292   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -4.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -3.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -5.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -6.1000    0.0000 Cl  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
    1.4917   -0.8667    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   -1.2792    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  3  2  0
  3  1  1  0
  4  1  1  0
  5  8  1  0
  6  4  2  0
  7 11  1  0
  8 14  1  0
  9 13  1  0
 10  5  1  0
 11  2  1  0
 12  1  1  0
 13  7  1  0
 14  7  1  0
 15 10  2  0
 16 10  1  0
 17  5  1  0
 18 19  1  0
 19 16  2  0
 20 15  1  0
 21 18  1  0
 22 12  1  0
 23 12  2  0
 24 22  2  0
 25 23  1  0
 26 25  2  0
  2  6  1  0
 26 24  1  0
  9  5  1  0
 20 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA147003

   4-(4-Chloro-phenyl)-1-(1-phenyl-1H-pyrrol-3-ylmethyl)-piperidin-4-ol

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: 366.89

Molecular Weight (Monoisotopic): 366.1499

AlogP: 4.61

#Rotatable Bonds: 4

Polar Surface Area: 28.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.96

CX Basic pKa: 8.25

CX LogP: 4.45

CX LogD: 3.54

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.73

Np Likeness Score: -0.96

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