4-pyridyl-cyanoguanidine derivative

ID: ALA363430

PubChem CID: 10281586

Max Phase: Preclinical

Molecular Formula: C24H34Cl3N7O3

Molecular Weight: 503.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N#CN/C(=N\CCCCCCOc1ccc(Cl)cc1)Nc1cc[n+](COC(=O)NCCCN)cc1.[Cl-]

Standard InChI:  InChI=1S/C24H32ClN7O3.2ClH/c25-20-6-8-22(9-7-20)34-17-4-2-1-3-13-28-23(30-18-27)31-21-10-15-32(16-11-21)19-35-24(33)29-14-5-12-26;;/h6-11,15-16H,1-5,12-14,17,19,26H2,(H2,28,29,30,33);2*1H

Standard InChI Key:  VIGGHMSBQOLPMS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 36  0  0  0  0  0  0  0  0999 V2000
    1.2929   -3.0716    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0946   -3.0716    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.6191   -2.9896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7398   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176   -3.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0571   -4.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7398   -2.9928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3381   -4.2100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4469   -3.7244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3381   -3.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4557   -1.7692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.7723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6342   -4.2952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6191   -2.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9032   -3.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1810   -2.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0571   -5.4336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1810   -2.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9032   -1.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788   -0.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408   -1.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7591   -0.6370    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.4920   -7.7168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566   -0.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788   -1.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408   -0.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566   -2.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7730   -6.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0186   -2.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7761   -5.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4920   -7.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3027   -1.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5828   -1.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4226   -2.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1385   -1.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8638   -2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4 11  1  0
  5  7  1  0
  6  8  1  0
  7  4  1  0
  8 10  1  0
  9  5  3  0
 10  3  1  0
 11 16  1  0
 12  4  2  0
 13  6  2  0
  3 14  2  0
 15  3  1  0
 16 18  1  0
 17  6  1  0
 18 15  2  0
 19 14  1  0
 20 25  2  0
 21 29  1  0
 22 20  1  0
 23 32  1  0
 24 26  2  0
 25 27  1  0
 26 21  1  0
 27 21  2  0
 28 31  1  0
 29 33  1  0
 30 12  1  0
 31 17  1  0
 32 28  1  0
 33 35  1  0
 34 30  1  0
 35 36  1  0
 36 37  1  0
 37 34  1  0
 19 16  2  0
 24 20  1  0
M  CHG  2   1  -1   3   1
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: 503.03

Molecular Weight (Monoisotopic): 502.2328

AlogP: 3.14

#Rotatable Bonds: 14

Polar Surface Area: 137.67

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.89

CX Basic pKa: 9.77

CX LogP: -1.00

CX LogD: -3.29

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.08

Np Likeness Score: -0.62

References

1. Binderup E, Björkling F, Hjarnaa PV, Latini S, Baltzer B, Carlsen M, Binderup L..  (2005)  EB1627: a soluble prodrug of the potent anticancer cyanoguanidine CHS828.,  15  (10): [PMID:15863303] [10.1016/j.bmcl.2005.03.064]

Source

Source(1):

• Scientific Literature