3-(1-(3-Fluorophenyl)-2-nitroethyl)-2-phenyl-1H-indole

ID: ALA4483407

PubChem CID: 155540736

Max Phase: Preclinical

Molecular Formula: C22H17FN2O2

Molecular Weight: 360.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])CC(c1cccc(F)c1)c1c(-c2ccccc2)[nH]c2ccccc12

Standard InChI:  InChI=1S/C22H17FN2O2/c23-17-10-6-9-16(13-17)19(14-25(26)27)21-18-11-4-5-12-20(18)24-22(21)15-7-2-1-3-8-15/h1-13,19,24H,14H2

Standard InChI Key:  XBRWORUVWLBYAO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   12.5479  -25.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2624  -25.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2606  -23.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9759  -24.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9761  -25.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7620  -25.3455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2474  -24.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7615  -24.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0690  -24.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4811  -25.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3050  -25.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7180  -24.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3009  -23.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4782  -23.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0161  -23.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8228  -23.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0774  -22.2679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4665  -22.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7227  -21.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1715  -21.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3638  -21.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1104  -22.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6634  -22.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8852  -22.0971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5264  -21.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3043  -22.3518    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3  6  2  0
  5  4  2  0
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  9 16  1  0
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 19 20  2  0
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 23 24  2  0
 24 19  1  0
 16 19  1  0
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 23 27  1  0
M  CHG  2  18   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4483407

   ---

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: 360.39

Molecular Weight (Monoisotopic): 360.1274

AlogP: 5.38

#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: 8.98

CX Basic pKa: ┄

CX LogP: 5.35

CX LogD: 5.34

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.38

Np Likeness Score: -0.79

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]

2. Schaffer PC,Kulkarni PM,Janero DR,Thakur GA.  (2020)  Focused structure-activity relationship profiling around the 2-phenylindole scaffold of a cannabinoid type-1 receptor agonist-positive allosteric modulator: site-III aromatic-ring congeners with enhanced activity and solubility.,  28  (21.0): [PMID:33065437] [10.1016/j.bmc.2020.115727]

Source

Source(1):

• Scientific Literature