3-Amino-N-carbamimidoyl-6-chloro-5-[2-(p-tolyl)ethylamino]pyrazine-2-carboxamide Hydrochloride

ID: ALA3818067

PubChem CID: 127050692

Max Phase: Preclinical

Molecular Formula: C15H19Cl2N7O

Molecular Weight: 347.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CCNc2nc(N)c(C(=O)N=C(N)N)nc2Cl)cc1.Cl

Standard InChI:  InChI=1S/C15H18ClN7O.ClH/c1-8-2-4-9(5-3-8)6-7-20-13-11(16)21-10(12(17)22-13)14(24)23-15(18)19;/h2-5H,6-7H2,1H3,(H3,17,20,22)(H4,18,19,23,24);1H

Standard InChI Key:  LSCCPZOUOTWTDD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    7.6876    2.2504    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8916   -4.9570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9336   -3.1588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912    5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1876    6.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1824    7.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8807    8.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5843    7.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    6.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8766    9.4579    0.0000 C   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  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
  5 14  1  0
  2 15  1  0
  3 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 347.81

Molecular Weight (Monoisotopic): 347.1261

AlogP: 1.09

#Rotatable Bonds: 5

Polar Surface Area: 145.30

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.18

CX LogP: 1.94

CX LogD: 1.74

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.47

Np Likeness Score: -0.83

References

1. Massink A, Louvel J, Adlere I, van Veen C, Huisman BJ, Dijksteel GS, Guo D, Lenselink EB, Buckley BJ, Matthews H, Ranson M, Kelso M, IJzerman AP..  (2016)  5'-Substituted Amiloride Derivatives as Allosteric Modulators Binding in the Sodium Ion Pocket of the Adenosine A2A Receptor.,  59  (10): [PMID:27124340] [10.1021/acs.jmedchem.6b00142]

Source

Source(1):

• Scientific Literature