9-(3-chlorobenzyl)-7-methoxy-1-methyl-2-(3-phenylpropyl)-9H-pyrido[3,4-b]indol-2-ium bromide

ID: ALA5287676

Max Phase: Preclinical

Molecular Formula: C29H28BrClN2O

Molecular Weight: 456.01

Names and Identifiers

Canonical SMILES:  COc1ccc2c3cc[n+](CCCc4ccccc4)c(C)c3n(Cc3cccc(Cl)c3)c2c1.[Br-]

Standard InChI:  InChI=1S/C29H28ClN2O.BrH/c1-21-29-27(15-17-31(21)16-7-11-22-8-4-3-5-9-22)26-14-13-25(33-2)19-28(26)32(29)20-23-10-6-12-24(30)18-23;/h3-6,8-10,12-15,17-19H,7,11,16,20H2,1-2H3;1H/q+1;/p-1

Standard InChI Key:  QORQXIOXXLTUNV-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    3.8173   -0.7684    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.8934    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4809    1.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6559    1.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434    1.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183    1.0906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908    0.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034   -0.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139    0.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2072   -0.3908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9937   -1.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770   -1.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3774   -1.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9570   -2.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7431   -2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -3.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3637   -2.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -3.9461    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9895   -0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -0.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4157   -0.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4157    0.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6986    1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9895    0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832    0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8516    1.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    1.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1301   -0.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1301   -1.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4811    3.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8929    3.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182    3.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1301    3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7219    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  7  6  2  0
  7  8  1  0
  9  7  1  0
 10  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 12  2  0
 16 18  1  0
 19 10  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 19 24  1  0
 24 25  1  0
 25  9  2  0
 25 26  1  0
 27 26  2  0
  6 27  1  0
 21 28  1  0
 28 29  1  0
 30  2  2  0
 31 30  1  0
 32 31  2  0
 33 32  1  0
 34 33  2  0
  2 34  1  0
M  CHG  2   1  -1   6   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 456.01

Molecular Weight (Monoisotopic): 455.1885

AlogP: 6.73

#Rotatable Bonds: 7

Polar Surface Area: 18.04

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.45

CX LogD: 2.45

Aromatic Rings: 5

Heavy Atoms: 33

QED Weighted: 0.25

Np Likeness Score: -0.40

References

1. Luo B, Song X..  (2021)  A comprehensive overview of β-carbolines and its derivatives as anticancer agents.,  224  [PMID:34332400] [10.1016/j.ejmech.2021.113688]

Source

Source(1):

• Scientific Literature