2,9-Dibenzyl-3-(carbonyl-phenylalanine ethyl ester)-bcarbolinium bromate

ID: ALA1095569

PubChem CID: 46193146

Max Phase: Preclinical

Molecular Formula: C37H34BrN3O3

Molecular Weight: 568.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@H](Cc1ccccc1)NC(=O)c1cc2c3ccccc3n(Cc3ccccc3)c2c[n+]1Cc1ccccc1.[Br-]

Standard InChI:  InChI=1S/C37H33N3O3.BrH/c1-2-43-37(42)32(22-27-14-6-3-7-15-27)38-36(41)34-23-31-30-20-12-13-21-33(30)40(25-29-18-10-5-11-19-29)35(31)26-39(34)24-28-16-8-4-9-17-28;/h3-21,23,26,32H,2,22,24-25H2,1H3;1H/t32-;/m0./s1

Standard InChI Key:  CIUPAQIBBTUKFC-UCRKPPETSA-N

Molfile:  

     RDKit          2D

 44 48  0  0  0  0  0  0  0  0999 V2000
    3.5250   -3.8125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.2302   -3.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5056   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2510   -2.7808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1179   -0.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6229   -1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -2.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354   -0.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649   -1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7715   -2.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0444   -1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0382   -2.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7512   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4710   -2.5448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4732   -1.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7595   -1.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1886   -1.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9021   -1.7168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1906   -0.4776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6176   -1.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3311   -1.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6195   -0.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0465   -1.3093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3291   -2.5451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7600   -1.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4754   -1.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8065   -3.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824   -3.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0612   -4.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7701   -5.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4913   -4.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3349   -0.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0442   -0.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7592   -0.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7615    0.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0430    1.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3310    0.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1836   -2.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1798   -3.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4627   -4.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586   -5.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1717   -5.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8905   -5.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8911   -4.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 23 25  1  0
 11 12  2  0
 25 26  1  0
  6  7  1  0
  3 27  2  0
 12 13  1  0
 27 28  1  0
  7 10  2  0
 28 29  2  0
 13 14  2  0
 29 30  1  0
  2  4  1  0
 30 31  2  0
 31  3  1  0
 14 15  1  0
 22 32  1  0
  9  8  2  0
 32 33  2  0
 15 16  2  0
 33 34  1  0
 16 11  1  0
 34 35  2  0
  8  5  1  0
 35 36  1  0
 15 17  1  0
 36 37  2  0
 37 32  1  0
  9 10  1  0
 14 38  1  0
 38 39  1  0
 17 18  1  0
 39 40  2  0
 17 19  2  0
 40 41  1  0
  2  3  1  0
 41 42  2  0
 18 20  1  0
 42 43  1  0
 10  4  1  0
 43 44  2  0
 44 39  1  0
 20 21  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: 568.70

Molecular Weight (Monoisotopic): 568.2595

AlogP: 6.08

#Rotatable Bonds: 10

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: 11.32

CX Basic pKa: ┄

CX LogP: 2.80

CX LogD: 2.80

Aromatic Rings: 6

Heavy Atoms: 43

QED Weighted: 0.16

Np Likeness Score: -0.41

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