N-{5-[1-(Benzenesulfonyl)-1H-indol-6-yl]-4-methyl-1H-imidazol-2-yl}propanamide

ID: ALA4483304

PubChem CID: 155540721

Max Phase: Preclinical

Molecular Formula: C21H20N4O3S

Molecular Weight: 408.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(=O)Nc1nc(C)c(-c2ccc3ccn(S(=O)(=O)c4ccccc4)c3c2)[nH]1

Standard InChI:  InChI=1S/C21H20N4O3S/c1-3-19(26)23-21-22-14(2)20(24-21)16-10-9-15-11-12-25(18(15)13-16)29(27,28)17-7-5-4-6-8-17/h4-13H,3H2,1-2H3,(H2,22,23,24,26)

Standard InChI Key:  IELIPILAHREMSR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   35.5149   -4.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8505   -3.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1801   -4.3434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4302   -5.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2551   -5.1345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9412   -5.7940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1212   -5.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6322   -6.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7903   -4.9471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8556   -3.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4864   -5.7748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7030   -4.9790    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.9055   -5.1893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2309   -3.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2297   -3.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9445   -4.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9427   -2.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6580   -3.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6582   -3.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4487   -4.1964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.9370   -3.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4483   -2.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5108   -5.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8634   -4.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0578   -4.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7642   -5.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1241   -5.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5697   -6.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8123   -6.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  2 10  1  0
 12 11  2  0
 13 12  2  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
 18 17  2  0
 17 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
 20 12  1  0
 12 23  1  0
 23 26  2  0
 27 24  1  0
 24 25  2  0
 25 23  1  0
 28 26  1  0
 27 28  2  0
 15  1  1  0
  8 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483304

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 408.48

Molecular Weight (Monoisotopic): 408.1256

AlogP: 3.93

#Rotatable Bonds: 5

Polar Surface Area: 96.85

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.03

CX Basic pKa: 3.10

CX LogP: 3.20

CX LogD: 3.19

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: -1.43

References

1. Hogendorf AS, Hogendorf A, Kurczab R, Kalinowska-Tłuścik J, Popik P, Nikiforuk A, Krawczyk M, Satała G, Lenda T, Knutelska J, Bugno R, Staroń J, Pietruś W, Matłoka M, Dubiel K, Moszczyński-Pętkowski R, Pieczykolan J, Wieczorek M, Pilarski B, Zajdel P, Bojarski AJ..  (2019)  2-Aminoimidazole-based antagonists of the 5-HT₆ receptor - A new concept in aminergic GPCR ligand design.,  179  [PMID:31229883] [10.1016/j.ejmech.2019.06.001]

Source

Source(1):

• Scientific Literature