7-n-Butoxy-9-(3-phenylpropyl)-2-benzyl-1-methyl-beta-carbolinium bromide

ID: ALA2314901

PubChem CID: 71575483

Max Phase: Preclinical

Molecular Formula: C32H35BrN2O

Molecular Weight: 463.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOc1ccc2c3cc[n+](Cc4ccccc4)c(C)c3n(CCCc3ccccc3)c2c1.[Br-]

Standard InChI:  InChI=1S/C32H35N2O.BrH/c1-3-4-22-35-28-17-18-29-30-19-21-33(24-27-14-9-6-10-15-27)25(2)32(30)34(31(29)23-28)20-11-16-26-12-7-5-8-13-26;/h5-10,12-15,17-19,21,23H,3-4,11,16,20,22,24H2,1-2H3;1H/q+1;/p-1

Standard InChI Key:  HOEKCISVNMURTE-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   17.2725  -14.2596    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   19.9411  -17.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2755  -16.3807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7913  -15.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9809  -15.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6506  -16.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8692  -16.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1643  -16.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4552  -16.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4552  -17.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1643  -18.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8692  -17.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6506  -17.8746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1266  -17.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4213  -17.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0457  -18.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7461  -18.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0411  -17.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0922  -16.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5174  -17.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1216  -17.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5461  -18.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3640  -18.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7554  -17.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3287  -17.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6240  -19.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8069  -19.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0425  -16.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3355  -16.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6271  -16.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3853  -19.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5696  -19.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1480  -20.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5434  -21.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3648  -21.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7827  -20.6829    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
 18 28  1  0
 28 29  1  0
 29 30  1  0
 27 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 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: 463.65

Molecular Weight (Monoisotopic): 463.2744

AlogP: 7.25

#Rotatable Bonds: 10

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: 3.17

CX LogD: 3.17

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.16

Np Likeness Score: -0.22

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