2-Benzyl-9-butyl-3-(carbonyl-phenylalanine ethyl ester)-bcarbolinium bromate

ID: ALA1095568

PubChem CID: 46193142

Max Phase: Preclinical

Molecular Formula: C34H36BrN3O3

Molecular Weight: 534.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1c2ccccc2c2cc(C(=O)N[C@@H](Cc3ccccc3)C(=O)OCC)[n+](Cc3ccccc3)cc21.[Br-]

Standard InChI:  InChI=1S/C34H35N3O3.BrH/c1-3-5-20-37-30-19-13-12-18-27(30)28-22-31(36(24-32(28)37)23-26-16-10-7-11-17-26)33(38)35-29(34(39)40-4-2)21-25-14-8-6-9-15-25;/h6-19,22,24,29H,3-5,20-21,23H2,1-2H3;1H/t29-;/m0./s1

Standard InChI Key:  CYTNOZVBQBCBGW-JMAPEOGHSA-N

Molfile:  

     RDKit          2D

 41 44  0  0  0  0  0  0  0  0999 V2000
    5.0792   -4.0875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.6677   -4.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9431   -5.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6885   -3.9017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -1.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0604   -2.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3872   -3.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3729   -1.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7024   -2.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2090   -3.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4819   -2.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4757   -3.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887   -4.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085   -3.6657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107   -2.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -2.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6261   -2.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3396   -2.8376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281   -1.5984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0551   -2.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7686   -2.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0570   -1.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4840   -2.4301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7666   -3.6659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -5.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2073   -6.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7724   -1.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1975   -2.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9129   -2.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4817   -1.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1967   -1.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1990   -0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4805    0.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7685   -0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -4.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6173   -4.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9003   -5.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8962   -6.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6093   -6.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3280   -6.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3286   -5.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18 20  1  0
 10  4  1  0
 20 21  1  0
  4 12  1  0
 20 22  1  1
 11  9  1  0
 21 23  1  0
  5  6  2  0
 21 24  2  0
 25  3  1  0
 11 12  2  0
 25 26  1  0
  6  7  1  0
 22 27  1  0
 12 13  1  0
 23 28  1  0
  7 10  2  0
 28 29  1  0
 13 14  2  0
 27 30  2  0
  2  4  1  0
 30 31  1  0
 14 15  1  0
 31 32  2  0
  9  8  2  0
 32 33  1  0
 15 16  2  0
 33 34  2  0
 34 27  1  0
 16 11  1  0
 14 35  1  0
 35 36  1  0
  8  5  1  0
 36 37  2  0
 15 17  1  0
 37 38  1  0
  9 10  1  0
 38 39  2  0
 17 18  1  0
 39 40  1  0
 17 19  2  0
 40 41  2  0
 41 36  1  0
  2  3  1  0
M  CHG  2   1  -1  14   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: 534.68

Molecular Weight (Monoisotopic): 534.2751

AlogP: 5.83

#Rotatable Bonds: 11

Polar Surface Area: 64.21

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.33

CX Basic pKa: ┄

CX LogP: 2.40

CX LogD: 2.40

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.17

Np Likeness Score: -0.43

References

1. Ma C, Cao R, Shi B, Li S, Chen Z, Yi W, Peng W, Ren Z, Song H..  (2010)  Synthesis and cytotoxic evaluation of N2-benzylated quaternary beta-carboline amino acid ester conjugates.,  45  (4): [PMID:20122764] [10.1016/j.ejmech.2009.12.060]

Source

Source(1):

• Scientific Literature