rac-3-(2-Nitro-1-(thiophen-2-yl)ethyl)-2-phenyl-1H-indole-6-carbonitrile

ID: ALA4483556

PubChem CID: 155540808

Max Phase: Preclinical

Molecular Formula: C21H15N3O2S

Molecular Weight: 373.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ccc2c(C(C[N+](=O)[O-])c3cccs3)c(-c3ccccc3)[nH]c2c1

Standard InChI:  InChI=1S/C21H15N3O2S/c22-12-14-8-9-16-18(11-14)23-21(15-5-2-1-3-6-15)20(16)17(13-24(25)26)19-7-4-10-27-19/h1-11,17,23H,13H2

Standard InChI Key:  HBOPEEJOMPTPGH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   30.2775  -12.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2763  -13.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9912  -13.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9894  -12.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7047  -12.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7050  -13.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4911  -13.7028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9767  -13.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4907  -12.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7984  -13.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2106  -13.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0348  -13.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4479  -13.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0307  -12.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2079  -12.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7453  -11.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5522  -11.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8069  -10.6245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2521  -10.0095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6112  -10.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1931  -10.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3668  -10.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6522   -9.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0392  -10.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3752  -11.0570    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.5658  -13.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8511  -14.2759    0.0000 N   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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
 26 27  3  0
  2 26  1  0
M  CHG  2  18   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4483556

   ---

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: 373.44

Molecular Weight (Monoisotopic): 373.0885

AlogP: 5.18

#Rotatable Bonds: 5

Polar Surface Area: 82.72

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.58

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 4.95

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: -1.24

References

1. Tseng CC, Baillie G, Donvito G, Mustafa MA, Juola SE, Zanato C, Massarenti C, Dall'Angelo S, Harrison WTA, Lichtman AH, Ross RA, Zanda M, Greig IR..  (2019)  The Trifluoromethyl Group as a Bioisosteric Replacement of the Aliphatic Nitro Group in CB₁ Receptor Positive Allosteric Modulators.,  62  (10): [PMID:31050898] [10.1021/acs.jmedchem.9b00252]

2. Tseng CC, Baillie G, Donvito G, Mustafa MA, Juola SE, Zanato C, Massarenti C, Dall'Angelo S, Harrison WTA, Lichtman AH, Ross RA, Zanda M, Greig IR..  (2019)  The Trifluoromethyl Group as a Bioisosteric Replacement of the Aliphatic Nitro Group in CB₁ Receptor Positive Allosteric Modulators.,  62  (10): [PMID:31050898] [10.1021/acs.jmedchem.9b00252]

3. Tseng CC, Baillie G, Donvito G, Mustafa MA, Juola SE, Zanato C, Massarenti C, Dall'Angelo S, Harrison WTA, Lichtman AH, Ross RA, Zanda M, Greig IR..  (2019)  The Trifluoromethyl Group as a Bioisosteric Replacement of the Aliphatic Nitro Group in CB₁ Receptor Positive Allosteric Modulators.,  62  (10): [PMID:31050898] [10.1021/acs.jmedchem.9b00252]

Source

Source(1):

• Scientific Literature