4-pyridyl-cyanoguanidine derivative

ID: ALA362089

PubChem CID: 53321722

Max Phase: Preclinical

Molecular Formula: C30H45Cl3N6O4

Molecular Weight: 588.17

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C30H43ClN6O4.2ClH/c31-26-12-14-28(15-13-26)39-22-10-7-5-9-19-34-29(35-24-33)36-27-16-20-37(21-17-27)25-41-30(38)40-23-11-6-3-1-2-4-8-18-32;;/h12-17,20-21H,1-11,18-19,22-23,25,32H2,(H,34,35);2*1H

Standard InChI Key:  UTWHXOBIFJGEFC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.0717   -2.2426    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9056   -0.6696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0318    0.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3168   -1.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0318   -0.6732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3426   -2.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6206   -1.8973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413   -1.4056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6206   -1.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7502    0.5615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3098    0.5615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9180   -1.9880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8796    0.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3391   -3.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4344    0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4468    1.6950    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1494    1.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.9209   -9.1273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344    1.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7124    0.1360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984    0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9209   -8.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0541   -3.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009    0.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2059   -8.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0541   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7760   -4.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1614    0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394    0.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4875   -6.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4875   -6.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7725   -5.5908    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  8  1  0
  8 10  1  0
  9  5  3  0
 10  3  1  0
 11 16  1  0
 12  4  2  0
 13  7  2  0
  3 14  2  0
 15  3  1  0
 16 18  1  0
 17 14  1  0
 18 15  2  0
 19  7  1  0
 20 24  2  0
 21 28  1  0
 22 20  1  0
 23 26  2  0
 24 27  1  0
 25 30  1  0
 26 21  1  0
 27 21  2  0
 28 32  1  0
 29 12  1  0
 30 34  1  0
 31 19  1  0
 32 36  1  0
 33 29  1  0
 34 38  1  0
 35 31  1  0
 36 40  1  0
 37 35  1  0
 38 41  1  0
 39 33  1  0
 40 39  1  0
 41 42  1  0
 42 43  1  0
 43 37  1  0
 17 16  2  0
 23 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: 588.17

Molecular Weight (Monoisotopic): 587.3107

AlogP: 5.91

#Rotatable Bonds: 20

Polar Surface Area: 134.87

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 10.21

CX LogP: 2.47

CX LogD: -0.14

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.03

Np Likeness Score: -0.39

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