2-(3-Bromo-9H-carbazol-9-yl)-N-ethyl-N-(3-methoxybenzyl)acetamide

ID: ALA4475609

PubChem CID: 155537862

Max Phase: Preclinical

Molecular Formula: C24H23BrN2O2

Molecular Weight: 451.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN(Cc1cccc(OC)c1)C(=O)Cn1c2ccccc2c2cc(Br)ccc21

Standard InChI:  InChI=1S/C24H23BrN2O2/c1-3-26(15-17-7-6-8-19(13-17)29-2)24(28)16-27-22-10-5-4-9-20(22)21-14-18(25)11-12-23(21)27/h4-14H,3,15-16H2,1-2H3

Standard InChI Key:  RGAIRSKRCFYXFB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   14.4288  -24.4497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0202  -25.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7704  -24.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9753  -24.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4292  -25.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6837  -26.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4782  -26.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0917  -24.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8355  -25.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3774  -26.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1755  -26.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4289  -25.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8854  -24.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4270  -23.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1338  -23.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1321  -22.4052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8424  -23.6295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8389  -21.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4235  -21.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5475  -22.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5451  -23.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2528  -23.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9606  -23.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9562  -22.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2479  -21.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4218  -21.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6616  -21.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3716  -22.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7209  -26.7555    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  8  1  1  0
  1  3  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  1 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 16 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 19 26  1  0
 24 27  1  0
 27 28  1  0
 11 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475609

   ---

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: 451.36

Molecular Weight (Monoisotopic): 450.0943

AlogP: 5.61

#Rotatable Bonds: 6

Polar Surface Area: 34.47

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.13

CX LogD: 5.13

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -1.47

References

1. Cheng HWA, Sokias R, Werry EL, Ittner LM, Reekie TA, Du J, Gao Q, Hibbs DE, Kassiou M..  (2019)  First Nondiscriminating Translocator Protein Ligands Produced from a Carbazole Scaffold.,  62  (17): [PMID:31419132] [10.1021/acs.jmedchem.9b00980]

Source

Source(1):

• Scientific Literature