2-(2-Oxo-2-(3,4,5-trimethoxyphenyl)ethyl)-9H-pyrido[3,4-b]indol-2-iumbromide

ID: ALA4101432

PubChem CID: 137658680

Max Phase: Preclinical

Molecular Formula: C22H21BrN2O4

Molecular Weight: 377.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)C[n+]2ccc3c(c2)[nH]c2ccccc23)cc(OC)c1OC.[Br-]

Standard InChI:  InChI=1S/C22H20N2O4.BrH/c1-26-20-10-14(11-21(27-2)22(20)28-3)19(25)13-24-9-8-16-15-6-4-5-7-17(15)23-18(16)12-24;/h4-12H,13H2,1-3H3;1H

Standard InChI Key:  FAKQBKNKOVTQTI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   19.4759   -4.1839    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.6127   -2.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3313   -3.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8638   -3.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4220   -2.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9563   -2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6793   -3.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3388   -3.9926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7868   -2.7253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0213   -3.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8254   -3.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3957   -3.1119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1564   -2.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3528   -2.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1980   -3.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7646   -2.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5670   -2.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5288   -1.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7969   -3.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5984   -3.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1658   -3.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9263   -2.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1253   -2.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9685   -3.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2053   -4.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4908   -1.8802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2938   -2.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8338   -4.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6360   -4.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9  6  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 21 24  1  0
 24 25  1  0
 22 26  1  0
 26 27  1  0
 20 28  1  0
 28 29  1  0
M  CHG  2   1  -1  12   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 377.42

Molecular Weight (Monoisotopic): 377.1496

AlogP: 3.52

#Rotatable Bonds: 6

Polar Surface Area: 64.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.17

CX Basic pKa: ┄

CX LogP: -1.31

CX LogD: -1.31

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: 0.20

References

1. Venkataramana Reddy PO, Mishra S, Tantak MP, Nikhil K, Sadana R, Shah K, Kumar D..  (2017)  Design, synthesis and in vitro cytotoxicity studies of novel β-carbolinium bromides.,  27  (6): [PMID:28254167] [10.1016/j.bmcl.2017.02.010]

Source

Source(1):

• Scientific Literature