2-Benzyl-3-(carbonyl-valine ethyl ester)-9-phenylpropyl-bcarbolinium bromate

ID: ALA1095570

PubChem CID: 46193148

Max Phase: Preclinical

Molecular Formula: C35H38BrN3O3

Molecular Weight: 548.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@@H](NC(=O)c1cc2c3ccccc3n(CCCc3ccccc3)c2c[n+]1Cc1ccccc1)C(C)C.[Br-]

Standard InChI:  InChI=1S/C35H37N3O3.BrH/c1-4-41-35(40)33(25(2)3)36-34(39)31-22-29-28-19-11-12-20-30(28)38(21-13-18-26-14-7-5-8-15-26)32(29)24-37(31)23-27-16-9-6-10-17-27;/h5-12,14-17,19-20,22,24-25,33H,4,13,18,21,23H2,1-3H3;1H/t33-;/m0./s1

Standard InChI Key:  ONJRCSLWLPJEPF-WAQYZQTGSA-N

Molfile:  

     RDKit          2D

 42 45  0  0  0  0  0  0  0  0999 V2000
    1.5834   -6.0875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.2052   -4.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260   -3.2392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071   -1.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021   -1.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753   -2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0896   -1.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2399   -1.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535   -2.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194   -2.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0132   -2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7262   -3.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4460   -3.0032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4482   -2.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345   -1.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -1.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8771   -2.1751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1656   -0.9359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926   -1.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3061   -2.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5945   -0.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0215   -1.7676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3041   -3.0034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7350   -2.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4504   -1.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3099   -0.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -4.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -5.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2648   -5.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9650   -5.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6891   -5.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7103   -6.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014   -6.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2802   -6.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8810   -0.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1586   -3.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1548   -4.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4378   -4.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337   -5.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1468   -5.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8655   -5.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -4.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 10  8  1  0
 19 21  1  1
  2  3  1  0
 20 22  1  0
  5  6  1  0
 20 23  2  0
 10 11  2  0
 22 24  1  0
  6  9  2  0
 24 25  1  0
 11 12  1  0
 21 26  1  0
  2 27  1  0
 12 13  2  0
 27 28  1  0
  8  7  2  0
 28 29  1  0
 13 14  1  0
 29 30  2  0
  7  4  1  0
 30 31  1  0
 14 15  2  0
 31 32  2  0
 15 10  1  0
 32 33  1  0
  8  9  1  0
 33 34  2  0
 34 29  1  0
 14 16  1  0
 21 35  1  0
 13 36  1  0
 36 37  1  0
 16 17  1  0
 37 38  2  0
  4  5  2  0
 38 39  1  0
 16 18  2  0
 39 40  2  0
  9  3  1  0
 40 41  1  0
 17 19  1  0
 41 42  2  0
 42 37  1  0
  3 11  1  0
M  CHG  2   1  -1  13   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: 548.71

Molecular Weight (Monoisotopic): 548.2908

AlogP: 6.08

#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: 2.77

CX LogD: 2.77

Aromatic Rings: 5

Heavy Atoms: 41

QED Weighted: 0.16

Np Likeness Score: -0.52

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