N-benzyl-5-(5-methoxy-1-(phenylsulfonyl)-1H-indol-3-yl)-4-methyl-1H-imidazol-2-amine

ID: ALA4520003

PubChem CID: 155542237

Max Phase: Preclinical

Molecular Formula: C26H24N4O3S

Molecular Weight: 472.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c(-c1[nH]c(NCc3ccccc3)nc1C)cn2S(=O)(=O)c1ccccc1

Standard InChI:  InChI=1S/C26H24N4O3S/c1-18-25(29-26(28-18)27-16-19-9-5-3-6-10-19)23-17-30(24-14-13-20(33-2)15-22(23)24)34(31,32)21-11-7-4-8-12-21/h3-15,17H,16H2,1-2H3,(H2,27,28,29)

Standard InChI Key:  WKDOWEAWARBZNI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   35.3816  -18.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5857  -18.8680    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.1713  -19.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1091  -17.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1080  -17.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.8210  -16.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5364  -17.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5413  -17.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3289  -18.0873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8108  -17.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.0398  -19.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2334  -19.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6852  -19.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9446  -20.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.0800  -15.2954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5578  -14.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3453  -14.8808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0228  -16.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3945  -16.6013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6801  -17.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2987  -13.8442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8475  -13.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5885  -12.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1405  -11.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8821  -11.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0733  -10.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5237  -11.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7851  -12.2839    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
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 10  2  1  0
  2 13  1  0
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 19 20  2  0
 20 23  1  0
 21 19  1  0
 12 19  1  0
 21 22  1  0
 22 23  2  0
 20 24  1  0
  4 25  1  0
 25 26  1  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4520003

   ---

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: 472.57

Molecular Weight (Monoisotopic): 472.1569

AlogP: 5.20

#Rotatable Bonds: 7

Polar Surface Area: 89.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.50

CX Basic pKa: 7.28

CX LogP: 4.31

CX LogD: 4.07

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.34

Np Likeness Score: -1.05

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