N-(5-(1-(3-fluorophenylsulfonyl)-5-methoxy-1H-indol-3-yl)-4-methyl-1H-imidazol-2-yl)acetamide

ID: ALA4521199

PubChem CID: 155542461

Max Phase: Preclinical

Molecular Formula: C21H19FN4O4S

Molecular Weight: 442.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c(-c1[nH]c(NC(C)=O)nc1C)cn2S(=O)(=O)c1cccc(F)c1

Standard InChI:  InChI=1S/C21H19FN4O4S/c1-12-20(25-21(23-12)24-13(2)27)18-11-26(19-8-7-15(30-3)10-17(18)19)31(28,29)16-6-4-5-14(22)9-16/h4-11H,1-3H3,(H2,23,24,25,27)

Standard InChI Key:  FSYOAGJDQOUMRH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   35.8503  -15.9459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0669  -15.1501    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.2694  -15.3604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5946  -13.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5935  -14.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3083  -14.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3065  -12.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0219  -13.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0221  -14.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8126  -14.3674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3009  -13.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8122  -13.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8748  -15.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2274  -14.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4218  -14.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1282  -16.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4863  -15.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9326  -16.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0681  -12.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8527  -11.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8524  -11.1617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0676  -10.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5830  -11.5746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8124  -10.1225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3641   -9.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1089   -8.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1712   -9.6804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8800  -12.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1657  -13.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1871  -17.0609    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.5203  -12.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 10  2  1  0
  2 13  1  0
 13 16  2  0
 17 14  1  0
 14 15  2  0
 15 13  1  0
 18 16  1  0
 17 18  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
 12 19  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
  4 28  1  0
 28 29  1  0
 18 30  1  0
 20 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521199

   ---

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: 442.47

Molecular Weight (Monoisotopic): 442.1111

AlogP: 3.68

#Rotatable Bonds: 5

Polar Surface Area: 106.08

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.03

CX Basic pKa: 2.93

CX LogP: 2.49

CX LogD: 2.48

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: -1.36

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