6-[3-(4-Benzyl-piperidin-1-yl)-prop-1-ynyl]-1-methyl-1,3-dihydro-benzoimidazol-2-one

ID: ALA114667

PubChem CID: 10737190

Max Phase: Preclinical

Molecular Formula: C23H25N3O

Molecular Weight: 359.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(O)nc2ccc(C#CCN3CCC(Cc4ccccc4)CC3)cc21

Standard InChI:  InChI=1S/C23H25N3O/c1-25-22-17-19(9-10-21(22)24-23(25)27)8-5-13-26-14-11-20(12-15-26)16-18-6-3-2-4-7-18/h2-4,6-7,9-10,17,20H,11-16H2,1H3,(H,24,27)

Standard InChI Key:  VLIKCDNWZRYWFS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   11.0042   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4042   -1.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6417   -2.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6750   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8250   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2875   -1.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8292   -2.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9042   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1875   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9167   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3917   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -3.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
  5  3  1  0
  6  7  3  0
  7 12  1  0
  8 13  1  0
  9  1  1  0
 10  4  2  0
 11  5  2  0
 12 10  1  0
 13  6  1  0
 14  8  1  0
 15  8  1  0
 16  2  1  0
 17 19  1  0
 18 11  1  0
 19 21  1  0
 20 17  1  0
 21 15  1  0
 22 14  1  0
 23 20  2  0
 24 20  1  0
 25 23  1  0
 26 24  2  0
 27 26  1  0
  4  5  1  0
 18 12  2  0
 19 22  1  0
 27 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA114667

   6-[3-(4-Benzyl-piperidin-1-yl)-prop-1-ynyl]-1-methyl-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: 359.47

Molecular Weight (Monoisotopic): 359.1998

AlogP: 3.59

#Rotatable Bonds: 3

Polar Surface Area: 41.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.56

CX Basic pKa: 8.02

CX LogP: 4.99

CX LogD: 4.28

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: -0.76

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