2-Guanidino-5-[(2-aminoimidazolino)benzyl]pyridine dihydrochloride

ID: ALA4799288

PubChem CID: 162676747

Max Phase: Preclinical

Molecular Formula: C16H21Cl2N7

Molecular Weight: 309.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.Cl.N=C(N)Nc1ccc(Cc2ccc(NC3=NCCN3)cc2)cn1

Standard InChI:  InChI=1S/C16H19N7.2ClH/c17-15(18)23-14-6-3-12(10-21-14)9-11-1-4-13(5-2-11)22-16-19-7-8-20-16;;/h1-6,10H,7-9H2,(H2,19,20,22)(H4,17,18,21,23);2*1H

Standard InChI Key:  YPIPHOAXIIEQKY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   44.7857  -23.3652    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   36.3694  -21.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3682  -21.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0830  -22.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7994  -21.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7966  -21.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0812  -20.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5095  -20.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2255  -21.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2252  -21.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9405  -22.2733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.6543  -21.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6486  -21.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9328  -20.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3709  -22.2669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.0833  -21.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6534  -22.2892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9392  -21.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0790  -21.0258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.7998  -22.2596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8525  -21.0578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0457  -20.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6326  -21.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1843  -22.2132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.2277  -21.1259    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
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  1  0
  3 17  1  0
 17 18  1  0
 16 19  2  0
 16 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 18  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: 309.38

Molecular Weight (Monoisotopic): 309.1702

AlogP: 1.35

#Rotatable Bonds: 4

Polar Surface Area: 111.21

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.18

CX LogP: 1.72

CX LogD: 0.56

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.43

Np Likeness Score: -0.57

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