7-Isobutoxy-2-benzyl-9-isobutyl-1-methyl-beta-carbolinium bromide

ID: ALA2314898

PubChem CID: 71575377

Max Phase: Preclinical

Molecular Formula: C27H33BrN2O

Molecular Weight: 401.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c2c(cc[n+]1Cc1ccccc1)c1ccc(OCC(C)C)cc1n2CC(C)C.[Br-]

Standard InChI:  InChI=1S/C27H33N2O.BrH/c1-19(2)16-29-26-15-23(30-18-20(3)4)11-12-24(26)25-13-14-28(21(5)27(25)29)17-22-9-7-6-8-10-22;/h6-15,19-20H,16-18H2,1-5H3;1H/q+1;/p-1

Standard InChI Key:  FZQBKFSLKLSMFW-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   15.8444   -3.0665    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   21.2619   -5.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5962   -4.5851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1120   -3.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3016   -4.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9713   -4.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1899   -5.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4850   -4.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7759   -5.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7759   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4850   -6.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1900   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9713   -6.0790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4473   -5.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7420   -5.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3664   -6.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0668   -6.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3618   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4129   -4.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8381   -5.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4423   -5.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8668   -6.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6847   -6.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0762   -5.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6494   -5.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9447   -7.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3401   -8.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1276   -7.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3632   -5.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6562   -4.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0716   -4.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
 12 13  1  0
 13 14  1  0
  6 14  2  0
  2 14  1  0
  2 15  1  0
 13 16  1  0
 17 18  1  0
 10 17  1  0
  3 19  1  0
 19 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
 16 26  1  0
 26 27  1  0
 26 28  1  0
 18 29  1  0
 29 30  1  0
 29 31  1  0
M  CHG  2   1  -1   3   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: 401.57

Molecular Weight (Monoisotopic): 401.2587

AlogP: 6.13

#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: 1.87

CX LogD: 1.87

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: -0.24

References

1. Cao R, Fan W, Guo L, Ma Q, Zhang G, Li J, Chen X, Ren Z, Qiu L..  (2013)  Synthesis and structure-activity relationships of harmine derivatives as potential antitumor agents.,  60  [PMID:23291116] [10.1016/j.ejmech.2012.11.045]

Source

Source(1):

• Scientific Literature