5-{3-[4-(4-Chloro-benzyl)-piperidin-1-yl]-prop-1-ynyl}-1,3-dihydro-benzoimidazol-2-one

ID: ALA325825

PubChem CID: 10547776

Max Phase: Preclinical

Molecular Formula: C22H22ClN3O

Molecular Weight: 379.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1nc2cc(C#CCN3CCC(Cc4ccc(Cl)cc4)CC3)ccc2[nH]1

Standard InChI:  InChI=1S/C22H22ClN3O/c23-19-6-3-17(4-7-19)14-18-9-12-26(13-10-18)11-1-2-16-5-8-20-21(15-16)25-22(27)24-20/h3-8,15,18H,9-14H2,(H2,24,25,27)

Standard InChI Key:  QAHMMZQSMDIJJU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   11.4417   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8417   -1.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0792   -2.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1125   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2625   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9250   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -1.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2667   -2.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3417   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7042   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6250   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8625   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250   -3.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8500   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875   -2.3667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4500   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3125   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  7  3  0
  7 11  1  0
  8 13  1  0
  9  1  1  0
 10  4  2  0
 11 10  1  0
 12  5  2  0
 13  6  1  0
 14  8  1  0
 15  8  1  0
 16 18  1  0
 17 22  2  0
 18 21  1  0
 19 12  1  0
 20 17  1  0
 21 26  1  0
 22 25  1  0
 23 24  2  0
 24 16  1  0
 25 16  2  0
 26 15  1  0
 27 14  1  0
  5  4  1  0
 11 19  2  0
 27 21  1  0
 17 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA325825

   5-{3-[4-(4-Chloro-benzyl)-piperidin-1-yl]-prop-1-ynyl}-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: 379.89

Molecular Weight (Monoisotopic): 379.1451

AlogP: 4.23

#Rotatable Bonds: 3

Polar Surface Area: 52.15

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.47

CX Basic pKa: 7.98

CX LogP: 5.21

CX LogD: 4.69

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -0.98

References

1. Wright JL, Gregory TF, Kesten SR, Boxer PA, Serpa KA, Meltzer LT, Wise LD, Espitia SA, Konkoy CS, Whittemore ER, Woodward RM..  (2000)  Subtype-selective N-methyl-D-aspartate receptor antagonists: synthesis and biological evaluation of 1-(heteroarylalkynyl)-4-benzylpiperidines.,  43  (18): [PMID:10978188] [10.1021/jm000023o]

Source

Source(1):

• Scientific Literature