1-(3-(4-(3-aminopropyl)piperazin-1-yl)propyl)-3-((3-(4-(3-aminopropyl)piperazin-1-yl)propyl)amino)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione

ID: ALA5286658

Max Phase: Preclinical

Molecular Formula: C32H51N9O2

Molecular Weight: 593.82

Names and Identifiers

Canonical SMILES:  NCCCN1CCN(CCCNC2=C(c3c[nH]c4ccccc34)C(=O)N(CCCN3CCN(CCCN)CC3)C2=O)CC1

Standard InChI:  InChI=1S/C32H51N9O2/c33-9-3-12-37-17-21-39(22-18-37)14-5-11-35-30-29(27-25-36-28-8-2-1-7-26(27)28)31(42)41(32(30)43)16-6-15-40-23-19-38(20-24-40)13-4-10-34/h1-2,7-8,25,35-36H,3-6,9-24,33-34H2

Standard InChI Key:  HNHWRICQFONUDJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 43 47  0  0  0  0  0  0  0  0999 V2000
   -1.1459   -1.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8134   -0.7112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584    0.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334    0.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785   -0.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9710    0.7881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459   -2.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208    0.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563    1.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0434    2.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707    1.6810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4382    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099    2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013    3.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2159    2.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185   -0.9247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5320   -1.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3291   -1.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5426   -2.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -2.9459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9231   -2.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7201   -2.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9337   -3.3731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3502   -3.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532   -3.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307   -3.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3142   -3.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6947   -2.6332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -0.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1939   -0.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5744    0.0285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3714   -0.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9549    0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7413    1.1955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9443    1.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3609    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3248    1.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1112    2.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6947    3.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4811    3.9565    0.0000 N   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  2  0
  5  1  1  0
  3  6  2  0
  1  7  2  0
  4  8  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  8  2  0
  9 13  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 10 16  1  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 25 24  1  0
 26 25  1  0
 21 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  2 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 35 34  1  0
 36 35  1  0
 37 36  1  0
 38 37  1  0
 39 38  1  0
 34 39  1  0
 37 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286658

   ---

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: 593.82

Molecular Weight (Monoisotopic): 593.4166

AlogP: 0.55

#Rotatable Bonds: 16

Polar Surface Area: 130.20

Molecular Species: BASE

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 10.17

CX LogP: -0.99

CX LogD: -6.87

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.16

Np Likeness Score: -0.46

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