Bis (ammonio) alkane analogue

ID: ALA263972

Cas Number: 505059-30-3

PubChem CID: 10440396

Max Phase: Preclinical

Molecular Formula: C40H48Br2N4O4

Molecular Weight: 648.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[N+](C)(CCCCCC[N+](C)(C)CCCN1C(=O)c2cccc3cccc(c23)C1=O)CCCN1C(=O)c2cccc3cccc(c23)C1=O.[Br-].[Br-]

Standard InChI:  InChI=1S/C40H48N4O4.2BrH/c1-43(2,27-13-23-41-37(45)31-19-9-15-29-16-10-20-32(35(29)31)38(41)46)25-7-5-6-8-26-44(3,4)28-14-24-42-39(47)33-21-11-17-30-18-12-22-34(36(30)33)40(42)48;;/h9-12,15-22H,5-8,13-14,23-28H2,1-4H3;2*1H/q+2;;/p-2

Standard InChI Key:  PTVCYHXWKZIOKB-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 50 53  0  0  0  0  0  0  0  0999 V2000
    9.1875   -2.2768    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.1365    0.8554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5032   -0.8554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7959   -1.4713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8438    1.4713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9662   -0.3080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6735    0.3080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8109   -0.0342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8287    0.0342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6228   -1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0168    1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438   -0.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0958    0.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735   -1.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2661    1.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155    0.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4242   -0.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0452   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5945    1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -1.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6885    1.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7931   -0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8465    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525   -2.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1871    2.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004   -1.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4392    1.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0302   -2.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6095    2.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6378    0.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0018   -0.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -0.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5182    0.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7809   -2.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8588    2.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3885   -0.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2511    0.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0602    0.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5794   -0.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5616   -0.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0780    0.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4687   -0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1531    0.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4866   -0.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1709    0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2333    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4064   -0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9840   -0.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6557    0.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3 17  2  0
  4 18  2  0
  5 19  2  0
  6 20  2  0
  7 17  1  0
  7 19  1  0
  7 31  1  0
  8 18  1  0
  8 20  1  0
  8 32  1  0
  9 39  1  0
  9 41  1  0
  9 43  1  0
  9 44  1  0
 10 40  1  0
 10 42  1  0
 10 45  1  0
 10 46  1  0
 11 13  1  0
 11 15  2  0
 11 21  1  0
 12 14  1  0
 12 16  2  0
 12 22  1  0
 13 17  1  0
 13 23  2  0
 14 18  1  0
 14 24  2  0
 15 19  1  0
 15 25  1  0
 16 20  1  0
 16 26  1  0
 21 27  1  0
 21 29  2  0
 22 28  1  0
 22 30  2  0
 23 33  1  0
 24 34  1  0
 25 35  2  0
 26 36  2  0
 27 33  2  0
 28 34  2  0
 29 35  1  0
 30 36  1  0
 31 37  1  0
 32 38  1  0
 37 39  1  0
 38 40  1  0
 41 47  1  0
 42 48  1  0
 47 49  1  0
 48 50  1  0
 49 50  1  0
M  CHG  4   1  -1   2  -1   9   1  10   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: 648.85

Molecular Weight (Monoisotopic): 648.3665

AlogP: 6.38

#Rotatable Bonds: 15

Polar Surface Area: 74.76

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -3.06

CX LogD: -3.06

Aromatic Rings: 4

Heavy Atoms: 48

QED Weighted: 0.09

Np Likeness Score: -0.14

References

1. Muth M, Bender W, Scharfenstein O, Holzgrabe U, Balatkova E, Tränkle C, Mohr K..  (2003)  Systematic development of high affinity bis(ammonio)alkane-type allosteric enhancers of muscarinic ligand binding.,  46  (6): [PMID:12620079] [10.1021/jm021017q]

2. Tischer M, Sologub L, Pradel G, Holzgrabe U..  (2010)  The bisnaphthalimides as new active lead compounds against Plasmodium falciparum.,  18  (9): [PMID:20382538] [10.1016/j.bmc.2010.03.067]

3. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays