1-((2R,6R)-1-(4-amino-3,5-dichlorobenzoyl)-2,6-dimethylpiperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

ID: ALA2402470

PubChem CID: 58324675

Max Phase: Preclinical

Molecular Formula: C21H22Cl2N4O2

Molecular Weight: 433.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1CC(n2c(=O)[nH]c3ccccc32)C[C@@H](C)N1C(=O)c1cc(Cl)c(N)c(Cl)c1

Standard InChI:  InChI=1S/C21H22Cl2N4O2/c1-11-7-14(27-18-6-4-3-5-17(18)25-21(27)29)8-12(2)26(11)20(28)13-9-15(22)19(24)16(23)10-13/h3-6,9-12,14H,7-8,24H2,1-2H3,(H,25,29)/t11-,12-/m1/s1

Standard InChI Key:  AOWNYHBHZWHKOU-VXGBXAGGSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   22.1715   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1715   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8836   -2.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5955   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5955   -1.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8836   -0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8836    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4576   -2.4178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7077   -2.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1565   -2.6953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3768   -3.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5724   -3.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3199   -4.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8707   -4.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6773   -4.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9261   -3.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3095   -2.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3112   -0.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0246   -1.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3136    0.0605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0205   -2.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7329   -2.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4496   -2.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4494   -1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7363   -0.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5367   -1.2743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1635   -2.4313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7302   -3.2532    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.1637   -0.7755    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11  8  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  4 17  1  6
  5 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 19  1  0
  9 26  2  0
 23 27  1  0
 22 28  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2402470

   3-[(2R,6R)-1-(4-amino-3,5-dichlorobenzoyl)-2,6-dimethylpiperidin-4-yl]-1H-benzimidazol-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: 433.34

Molecular Weight (Monoisotopic): 432.1120

AlogP: 4.47

#Rotatable Bonds: 2

Polar Surface Area: 84.12

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.90

CX Basic pKa: 0.85

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: -0.90

References

1. Deng X, Shen Y, Yang J, He J, Zhao Y, Peng LY, Leng Y, Zhao QS..  (2013)  Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.,  65  [PMID:23747808] [10.1016/j.ejmech.2013.05.010]

Source

Source(1):

• Scientific Literature