2-Benzyl-1-[(E)-2-(4-methoxy-phenyl)-vinyl]-9-(3-phenyl-propyl)-9H-beta-carbolin-2-ium bromide

ID: ALA488441

PubChem CID: 25154820

Max Phase: Preclinical

Molecular Formula: C36H33BrN2O

Molecular Weight: 509.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/c2c3c(cc[n+]2Cc2ccccc2)c2ccccc2n3CCCc2ccccc2)cc1.[Br-]

Standard InChI:  InChI=1S/C36H33N2O.BrH/c1-39-31-21-18-29(19-22-31)20-23-35-36-33(24-26-37(35)27-30-13-6-3-7-14-30)32-16-8-9-17-34(32)38(36)25-10-15-28-11-4-2-5-12-28;/h2-9,11-14,16-24,26H,10,15,25,27H2,1H3;1H/q+1;/p-1/b23-20+;

Standard InChI Key:  NAKHVIPNTVDTIW-NMSJBYGBSA-M

Molfile:  

     RDKit          2D

 40 44  0  0  0  0  0  0  0  0999 V2000
    3.1750   -8.8333    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8953   -5.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3787   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0389   -6.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0763   -5.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7338   -6.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182   -6.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7258   -7.5630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9419   -6.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9402   -7.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2214   -7.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4960   -7.2952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902   -6.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291   -6.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187   -8.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971   -8.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4998   -9.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2144  -10.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2120  -11.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043  -11.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198  -11.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2139  -10.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5081  -12.2445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2044  -12.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2126   -7.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9249   -7.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6423   -7.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3499   -7.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3486   -6.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286   -6.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9199   -6.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9752   -8.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7810   -8.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -9.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8362   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3914   -8.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1965   -9.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4450   -9.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8855  -10.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825  -10.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  2  0
 19 20  2  0
 20 21  1  0
  9 10  2  0
 21 22  2  0
 22 17  1  0
  6  5  2  0
 20 23  1  0
 10 11  1  0
 23 24  1  0
  5  2  1  0
 12 25  1  0
 11 12  2  0
 25 26  1  0
  6  7  1  0
 26 27  2  0
 12 13  1  0
 27 28  1  0
  2  3  2  0
 28 29  2  0
 13 14  2  0
 29 30  1  0
 14  9  1  0
 30 31  2  0
 31 26  1  0
  8 32  1  0
 11 15  1  0
 32 33  1  0
  3  4  1  0
 33 34  1  0
 15 16  2  0
 34 35  1  0
  7  8  1  0
 35 36  2  0
 16 17  1  0
 36 37  1  0
  8 10  1  0
 37 38  2  0
 17 18  2  0
 38 39  1  0
  9  6  1  0
 39 40  2  0
 40 35  1  0
 18 19  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: 509.67

Molecular Weight (Monoisotopic): 509.2587

AlogP: 7.94

#Rotatable Bonds: 9

Polar Surface Area: 18.04

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.29

CX LogD: 4.29

Aromatic Rings: 6

Heavy Atoms: 39

QED Weighted: 0.18

Np Likeness Score: -0.16

References

1. Cao R, Yi W, Wu Q, Guan X, Feng M, Ma C, Chen Z, Song H, Peng W..  (2008)  Synthesis and cytotoxic activities of 1-benzylidine substituted beta-carboline derivatives.,  18  (24): [PMID:18952426] [10.1016/j.bmcl.2008.10.043]

2. 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