{4-[3-(Propyl)guanidino]-4'-(2-aminoimidazolino)}-1,2-diphenylethane dihydrochloride

ID: ALA4800044

PubChem CID: 162677109

Max Phase: Preclinical

Molecular Formula: C21H30Cl2N6

Molecular Weight: 364.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCNC(=N)Nc1ccc(CCc2ccc(NC3=NCCN3)cc2)cc1.Cl.Cl

Standard InChI:  InChI=1S/C21H28N6.2ClH/c1-2-13-23-20(22)26-18-9-5-16(6-10-18)3-4-17-7-11-19(12-8-17)27-21-24-14-15-25-21;;/h5-12H,2-4,13-15H2,1H3,(H3,22,23,26)(H2,24,25,27);2*1H

Standard InChI Key:  JFDIHKZOVTZKLZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   30.6134   -7.0714    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.0572   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0560   -4.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7709   -4.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4873   -4.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4845   -3.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7691   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3427   -3.0044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6282   -3.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8774   -3.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3254   -3.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7382   -4.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5450   -4.2391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2025   -4.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9162   -4.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6314   -4.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6280   -5.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3424   -5.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0571   -5.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0532   -4.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3383   -4.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7728   -5.8842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4861   -5.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4837   -4.6446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2018   -5.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9150   -5.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6307   -5.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3440   -5.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4366   -3.8009    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  2  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
  5 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  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: 364.50

Molecular Weight (Monoisotopic): 364.2375

AlogP: 3.19

#Rotatable Bonds: 7

Polar Surface Area: 84.33

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.13

CX LogP: 3.94

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: -0.44

References

1. McMullan M,Kelly B,Mihigo HB,Keogh AP,Rodriguez F,Brocos-Mosquera I,García-Bea A,Miranda-Azpiazu P,Callado LF,Rozas I.  (2021)  Di-aryl guanidinium derivatives: Towards improved α2-Adrenergic affinity and antagonist activity.,  209  [PMID:33139112] [10.1016/j.ejmech.2020.112947]

Source

Source(1):

• Scientific Literature