N1,N1-bis-(2-aminoethyl)-N'-(pyren-1-ylmethyl)ethane-1,2-diamine trihydrochloride salt

ID: ALA4475528

PubChem CID: 155537978

Max Phase: Preclinical

Molecular Formula: C23H31Cl3N4

Molecular Weight: 360.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.Cl.Cl.NCCN(CCN)CCNCc1ccc2ccc3cccc4ccc1c2c34

Standard InChI:  InChI=1S/C23H28N4.3ClH/c24-10-13-27(14-11-25)15-12-26-16-20-7-6-19-5-4-17-2-1-3-18-8-9-21(20)23(19)22(17)18;;;/h1-9,26H,10-16,24-25H2;3*1H

Standard InChI Key:  VCCJQYWYDHOXNE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
    4.6620   -9.7700    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4902  -11.8326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090  -12.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238  -11.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426  -12.2493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3614  -11.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426  -13.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238  -13.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238  -14.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0803  -12.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7991  -11.8326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5179  -12.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2368  -11.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9496  -10.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2342  -11.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9557  -12.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9559  -13.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6684  -13.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3838  -13.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0972  -13.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8101  -13.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8050  -12.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6688  -11.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3800  -12.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0902  -11.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0906  -11.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3748  -10.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6674  -11.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9187  -13.9455    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.7836  -13.4996    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 16  2  0
 28 14  1  0
 14 15  2  0
 15 13  1  0
 23 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 24 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 25  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 23  2  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 360.51

Molecular Weight (Monoisotopic): 360.2314

AlogP: 2.89

#Rotatable Bonds: 9

Polar Surface Area: 67.31

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.83

CX LogP: 2.27

CX LogD: -3.51

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: -0.44

References

1. Martín-Escolano R, Molina-Carreño D, Delgado-Pinar E, Martin-Montes Á, Clares MP, Medina-Carmona E, Pitarch-Jarque J, Martín-Escolano J, Rosales MJ, García-España E, Sánchez-Moreno M, Marín C..  (2019)  New polyamine drugs as more effective antichagas agents than benznidazole in both the acute and chronic phases.,  164  [PMID:30583247] [10.1016/j.ejmech.2018.12.034]

Source

Source(1):

• Scientific Literature