4-pyridyl-cyanoguanidine derivative

ID: ALA189208

PubChem CID: 10144983

Max Phase: Preclinical

Molecular Formula: C26H35Cl2N5O6

Molecular Weight: 549.05

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H34ClN5O6.ClH/c1-34-16-17-35-18-19-37-26(33)38-21-32-13-10-23(11-14-32)31-25(30-20-28)29-12-4-2-3-5-15-36-24-8-6-22(27)7-9-24;/h6-11,13-14H,2-5,12,15-19,21H2,1H3,(H,29,30);1H

Standard InChI Key:  SVVFERHIJRKZJB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 39  0  0  0  0  0  0  0  0999 V2000
    2.4542    0.1333    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    1.0708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917    1.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125    0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917    1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042    1.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250    0.2708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792    2.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042    2.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    1.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208    1.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1500    3.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7250    2.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8625    3.5875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.4292    3.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1500    2.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7167    3.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4375    1.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0042    1.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7083    1.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5708    0.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250    1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2917    2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9958    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833    1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4208    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4375    2.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5792    1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1542    1.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8667    2.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  5  1  0
  4  3  1  0
  5 10  1  0
  6  7  1  0
  7  9  1  0
  8  4  3  0
  9  2  1  0
 10 14  1  0
 11  6  2  0
 12  2  2  0
 13  2  1  0
 14 17  1  0
 15  5  2  0
 16 12  1  0
 17 13  2  0
 18  6  1  0
 19 22  1  0
 20 26  1  0
 21 19  1  0
 22 24  2  0
 23 25  1  0
 24 20  1  0
 25 20  2  0
 26 31  1  0
 27 32  1  0
 28 34  1  0
 29 15  1  0
 30 18  1  0
 31 37  1  0
 32 33  1  0
 33 28  1  0
 34 30  1  0
 35 27  1  0
 36 29  1  0
 37 39  1  0
 38 36  1  0
 39 38  1  0
 14 16  2  0
 23 19  2  0
M  CHG  2   1  -1   2   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: 549.05

Molecular Weight (Monoisotopic): 548.2270

AlogP: 3.88

#Rotatable Bonds: 17

Polar Surface Area: 127.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 1.27

CX LogP: 0.37

CX LogD: 0.37

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.06

Np Likeness Score: -0.67

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