1-Methyl-2-benzyl-7-benzyloxy-9-benzyl-beta-carbolin-2-ium bromide

ID: ALA2164716

PubChem CID: 54766737

Max Phase: Preclinical

Molecular Formula: C33H29BrN2O

Molecular Weight: 469.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c2c(cc[n+]1Cc1ccccc1)c1ccc(OCc3ccccc3)cc1n2Cc1ccccc1.[Br-]

Standard InChI:  InChI=1S/C33H29N2O.BrH/c1-25-33-31(19-20-34(25)22-26-11-5-2-6-12-26)30-18-17-29(36-24-28-15-9-4-10-16-28)21-32(30)35(33)23-27-13-7-3-8-14-27;/h2-21H,22-24H2,1H3;1H/q+1;/p-1

Standard InChI Key:  SEZZOMVRRQGVSJ-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   23.3397  -14.0832    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   16.6675  -14.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6664  -15.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3812  -15.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3794  -13.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0949  -14.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0952  -15.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8822  -15.3041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8809  -13.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3652  -14.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1826  -14.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5167  -13.7946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0275  -13.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2117  -13.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9514  -15.4663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6683  -15.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2372  -15.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5223  -15.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8067  -15.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0923  -15.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0912  -16.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8105  -16.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5219  -16.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3415  -13.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7727  -14.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3775  -15.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8080  -15.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6337  -15.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0271  -15.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5943  -14.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2745  -16.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8422  -16.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0170  -16.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5847  -17.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9772  -18.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8063  -18.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2347  -17.4511    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
  3 15  1  0
 11 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 12 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
  8 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 32  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: 469.61

Molecular Weight (Monoisotopic): 469.2274

AlogP: 7.07

#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: 2.83

CX LogD: 2.83

Aromatic Rings: 6

Heavy Atoms: 36

QED Weighted: 0.23

Np Likeness Score: -0.25

References

1. Frédérick R, Bruyère C, Vancraeynest C, Reniers J, Meinguet C, Pochet L, Backlund A, Masereel B, Kiss R, Wouters J..  (2012)  Novel trisubstituted harmine derivatives with original in vitro anticancer activity.,  55  (14): [PMID:22770529] [10.1021/jm300542e]

2. Meinguet C, Bruyère C, Frédérick R, Mathieu V, Vancraeynest C, Pochet L, Laloy J, Mortier J, Wolber G, Kiss R, Masereel B, Wouters J..  (2015)  3D-QSAR, design, synthesis and characterization of trisubstituted harmine derivatives with in vitro antiproliferative properties.,  94  [PMID:25747498] [10.1016/j.ejmech.2015.02.044]

3. 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