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

ID: ALA4518499

PubChem CID: 155541492

Max Phase: Preclinical

Molecular Formula: C23H21BrN2O2

Molecular Weight: 437.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(CN(C)C(=O)Cn2c3ccccc3c3cc(Br)ccc32)c1

Standard InChI:  InChI=1S/C23H21BrN2O2/c1-25(14-16-6-5-7-18(12-16)28-2)23(27)15-26-21-9-4-3-8-19(21)20-13-17(24)10-11-22(20)26/h3-13H,14-15H2,1-2H3

Standard InChI Key:  CDLCLZWDPZJVCC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.3996   -3.8218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9910   -5.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7412   -4.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9461   -4.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -4.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6546   -5.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4491   -5.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0626   -4.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8064   -5.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3482   -5.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1464   -5.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3998   -4.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8562   -4.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978   -3.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1047   -2.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1029   -1.7773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8133   -3.0016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8098   -1.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3943   -1.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5183   -1.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159   -2.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2236   -2.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9314   -2.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9271   -1.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2187   -1.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6324   -1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3425   -1.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -6.1276    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
 24 26  1  0
 26 27  1  0
 11 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4518499

   ---

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: 437.34

Molecular Weight (Monoisotopic): 436.0786

AlogP: 5.22

#Rotatable Bonds: 5

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: 4.77

CX LogD: 4.77

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -1.44

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