Dibenzyl ((13S,18S)-15,16-dibromo-9,12,19,22-tetraoxo-4,8,11,20,23,27-hexaazatriacontane-13,18-diyl)dicarbamate

ID: ALA5280891

Max Phase: Preclinical

Molecular Formula: C40H60Br2N8O8

Molecular Weight: 940.78

Names and Identifiers

Canonical SMILES:  CCCNCCCNC(=O)CNC(=O)[C@H](CC(Br)C(Br)C[C@H](NC(=O)OCc1ccccc1)C(=O)NCC(=O)NCCCNCCC)NC(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C40H60Br2N8O8/c1-3-17-43-19-11-21-45-35(51)25-47-37(53)33(49-39(55)57-27-29-13-7-5-8-14-29)23-31(41)32(42)24-34(50-40(56)58-28-30-15-9-6-10-16-30)38(54)48-26-36(52)46-22-12-20-44-18-4-2/h5-10,13-16,31-34,43-44H,3-4,11-12,17-28H2,1-2H3,(H,45,51)(H,46,52)(H,47,53)(H,48,54)(H,49,55)(H,50,56)/t31?,32?,33-,34-/m0/s1

Standard InChI Key:  YNELDCFOTDEPEA-TYBYDDOHSA-N

Molfile:  

 
     RDKit          2D

 58 59  0  0  0  0  0  0  0  0999 V2000
   -3.9296    4.1255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    4.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    4.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    4.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709    4.1253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    4.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    4.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733    2.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    5.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6443    4.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6443    5.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3591    5.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    1.6494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561   -0.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709   -1.6517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856   -0.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    0.4114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    0.8241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -0.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    2.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6445    2.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3593    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0740    2.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2174    1.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026    2.8874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6468    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561   -2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561   -2.8897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585   -1.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585   -3.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585   -4.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0732   -4.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724   -5.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -5.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3544   -5.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3592   -4.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3618    2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0740    1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0740    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3636    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6468    0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    0.8238    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.0729    0.4116    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  6 12  2  0
  1 13  1  0
 13 14  1  0
 14 15  1  0
 10 16  1  1
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 16 37  1  0
 37 38  1  0
 37 39  2  0
 38 40  1  0
 40 41  1  0
 22 42  1  0
 42 43  1  0
 42 44  2  0
 43 45  1  0
 45 46  1  0
 47 46  2  0
 48 47  1  0
 49 48  2  0
 50 49  1  0
 51 50  2  0
 46 51  1  0
 52 41  2  0
 53 52  1  0
 54 53  2  0
 55 54  1  0
 56 55  2  0
 41 56  1  0
 19 57  1  0
 18 58  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280891

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 940.78

Molecular Weight (Monoisotopic): 938.2901

AlogP: 3.13

#Rotatable Bonds: 29

Polar Surface Area: 217.12

Molecular Species: BASE

HBA: 10

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.95

CX Basic pKa: 10.76

CX LogP: 1.72

CX LogD: -3.71

Aromatic Rings: 2

Heavy Atoms: 58

QED Weighted: 0.04

Np Likeness Score: -0.29

References

1. Jagu E, Pomel S, Pethe S, Loiseau PM, Labruère R..  (2017)  Polyamine-based analogs and conjugates as antikinetoplastid agents.,  139  [PMID:28886510] [10.1016/j.ejmech.2017.08.014]

Source

Source(1):

• Scientific Literature