6-Fluoro-2-(3-fluorophenyl)-3-(1-(4-fluorophenyl)-2-nitroethyl)-1H-indole

ID: ALA4483342

PubChem CID: 155540863

Max Phase: Preclinical

Molecular Formula: C22H15F3N2O2

Molecular Weight: 396.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])CC(c1ccc(F)cc1)c1c(-c2cccc(F)c2)[nH]c2cc(F)ccc12

Standard InChI:  InChI=1S/C22H15F3N2O2/c23-15-6-4-13(5-7-15)19(12-27(28)29)21-18-9-8-17(25)11-20(18)26-22(21)14-2-1-3-16(24)10-14/h1-11,19,26H,12H2

Standard InChI Key:  WYUBIKKWGGXYPV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   11.7731  -15.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7720  -16.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4867  -16.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4849  -15.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2004  -15.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2006  -16.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9867  -16.7732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4723  -16.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9862  -15.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2940  -16.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7062  -16.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5304  -16.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9435  -16.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5262  -15.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7034  -15.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2409  -14.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0478  -14.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3024  -13.6948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6911  -14.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9474  -13.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3960  -12.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881  -12.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3347  -13.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8878  -14.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1104  -13.5239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7513  -13.0829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0573  -16.9345    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0351  -12.2024    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.9427  -17.5357    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
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  6  7  1  0
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  8  9  2  0
  9  5  1  0
 10 11  2  0
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 12 13  2  0
 13 14  1  0
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 15 10  1  0
  8 10  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 16 19  1  0
 18 25  1  0
 18 26  2  0
  2 27  1  0
 22 28  1  0
 12 29  1  0
M  CHG  2  18   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4483342

   ---

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: 396.37

Molecular Weight (Monoisotopic): 396.1086

AlogP: 5.66

#Rotatable Bonds: 5

Polar Surface Area: 58.93

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.09

CX Basic pKa: ┄

CX LogP: 5.63

CX LogD: 5.63

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.35

Np Likeness Score: -0.83

References

1. Garai S, Kulkarni PM, Schaffer PC, Leo LM, Brandt AL, Zagzoog A, Black T, Lin X, Hurst DP, Janero DR, Abood ME, Zimmowitch A, Straiker A, Pertwee RG, Kelly M, Szczesniak AM, Denovan-Wright EM, Mackie K, Hohmann AG, Reggio PH, Laprairie RB, Thakur GA..  (2020)  Application of Fluorine- and Nitrogen-Walk Approaches: Defining the Structural and Functional Diversity of 2-Phenylindole Class of Cannabinoid 1 Receptor Positive Allosteric Modulators.,  63  (2): [PMID:31756109] [10.1021/acs.jmedchem.9b01142]

Source

Source(1):

• Scientific Literature