2-(2-(Propyl)guanidino)]-5[4-(2-aminoimidazolino)benzyl]pyridine dihydrochloride

ID: ALA4745647

PubChem CID: 162648277

Max Phase: Preclinical

Molecular Formula: C19H27Cl2N7

Molecular Weight: 351.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H25N7.2ClH/c1-2-9-21-18(20)26-17-8-5-15(13-24-17)12-14-3-6-16(7-4-14)25-19-22-10-11-23-19;;/h3-8,13H,2,9-12H2,1H3,(H2,22,23,25)(H3,20,21,24,26);2*1H

Standard InChI Key:  OFLVIOYZWFGNNZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   30.9080  -29.9063    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.5175  -27.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5163  -28.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2310  -28.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9475  -28.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9446  -27.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2292  -27.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6574  -27.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3734  -27.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3731  -28.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0882  -28.6624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8021  -28.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7963  -27.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0807  -27.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5185  -28.6560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2309  -28.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8015  -28.6784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0875  -28.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2267  -27.4151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9473  -28.6487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0008  -27.4471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1941  -27.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7810  -27.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3326  -28.6024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6597  -28.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3761  -28.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0885  -28.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1437  -26.8714    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
 20 25  1  0
 25 26  1  0
 26 27  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: 351.46

Molecular Weight (Monoisotopic): 351.2171

AlogP: 2.39

#Rotatable Bonds: 6

Polar Surface Area: 97.22

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.30

CX LogP: 2.88

CX LogD: 1.50

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: -0.67

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