4-pyridyl-cyanoguanidine derivative

ID: ALA189478

PubChem CID: 53325701

Max Phase: Preclinical

Molecular Formula: C25H35Cl3N6O3

Molecular Weight: 502.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H](N)C(=O)OC[n+]1ccc(N/C(=N/CCCCCCOc2ccc(Cl)cc2)NC#N)cc1.Cl.[Cl-]

Standard InChI:  InChI=1S/C25H33ClN6O3.2ClH/c1-19(2)23(28)24(33)35-18-32-14-11-21(12-15-32)31-25(30-17-27)29-13-5-3-4-6-16-34-22-9-7-20(26)8-10-22;;/h7-12,14-15,19,23H,3-6,13,16,18,28H2,1-2H3,(H,29,30);2*1H/t23-;;/m1../s1

Standard InChI Key:  CAVWZDUEUBYNLK-MQWQBNKOSA-N

Molfile:  

     RDKit          2D

 37 36  0  0  0  0  0  0  0  0999 V2000
    2.2547   -1.3409    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0164   -1.5041    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5460   -3.6238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633   -2.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379   -4.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633   -3.6270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9905   -5.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664   -4.3555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2682   -4.8391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2682   -4.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -2.4085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9874   -6.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9347   -2.4117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5652   -4.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5460   -2.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8269   -4.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046   -2.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046   -3.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8269   -2.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4095   -6.3810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7096   -6.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752   -1.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370   -2.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8562   -1.2844    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5530   -1.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752   -2.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370   -1.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5530   -2.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1085   -2.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219   -2.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2874   -6.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7096   -7.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -2.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997   -2.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360   -2.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0520   -2.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7773   -2.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4 11  1  0
  5  6  1  0
  6  4  1  0
  7  9  1  0
  8  5  3  0
  9 10  1  0
 10  3  1  0
 11 17  1  0
 12  7  1  0
 13  4  2  0
 14  7  2  0
  3 15  2  0
 16  3  1  0
 17 18  1  0
 18 16  2  0
 19 15  1  0
 12 20  1  1
 21 12  1  0
 22 26  2  0
 23 29  1  0
 24 22  1  0
 25 27  2  0
 26 28  1  0
 27 23  1  0
 28 23  2  0
 29 33  1  0
 30 13  1  0
 31 21  1  0
 32 21  1  0
 33 35  1  0
 34 30  1  0
 35 36  1  0
 36 37  1  0
 37 34  1  0
 19 17  2  0
 25 22  1  0
M  CHG  2   2  -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: 502.04

Molecular Weight (Monoisotopic): 501.2375

AlogP: 3.59

#Rotatable Bonds: 13

Polar Surface Area: 125.64

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.47

CX LogP: 0.38

CX LogD: 0.04

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.07

Np Likeness Score: -0.43

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