1-((S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one

ID: ALA5208197

PubChem CID: 138621427

Max Phase: Preclinical

Molecular Formula: C21H23N3O3

Molecular Weight: 365.43

Names and Identifiers

Canonical SMILES:  O=c1[nH]c2ccccc2n1[C@H]1CCCN(C[C@H]2COc3ccccc3O2)C1

Standard InChI:  InChI=1S/C21H23N3O3/c25-21-22-17-7-1-2-8-18(17)24(21)15-6-5-11-23(12-15)13-16-14-26-19-9-3-4-10-20(19)27-16/h1-4,7-10,15-16H,5-6,11-14H2,(H,22,25)/t15-,16-/m0/s1

Standard InChI Key:  DEZPQGQCIGDIAA-HOTGVXAUSA-N

Molfile:  

 
     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   -2.7992    0.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3703    0.5286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0585    2.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729    1.7662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4873    2.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2018    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2018    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4873    0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4873   -0.2960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8200   -0.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0354   -0.5261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748   -1.5656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999   -1.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519   -2.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2588   -2.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -1.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617   -0.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1547   -0.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3703    2.1787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7992    2.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5137    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5137    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  6  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 11 12  1  6
 13 12  1  0
 13 14  2  0
 15 13  1  0
 16 15  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 21 20  1  0
 21 16  2  0
 21 12  1  0
 22 11  1  0
  7 22  1  0
  5 23  1  0
 24 23  1  0
  2 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27  1  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5208197

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 365.43

Molecular Weight (Monoisotopic): 365.1739

AlogP: 2.81

#Rotatable Bonds: 3

Polar Surface Area: 59.49

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.89

CX Basic pKa: 7.48

CX LogP: 3.05

CX LogD: 2.71

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -0.85

References

1. Wang S, Haikarainen A, Pohjakallio A, Sipilä J, Kaskinoro J, Juhila S, Jalava N, Koskinen M, Vesajoki M, Kumpulainen E, Pystynen J, Koskelainen T, Holm P, Din Belle D..  (2022)  2,3-Dihydrobenzo-dioxine piperidine derivatives as potent and selective α2c antagonists.,  69  [PMID:35569686] [10.1016/j.bmcl.2022.128783]

Source

Source(1):

• Scientific Literature