4-pyridyl-cyanoguanidine derivative

ID: ALA190412

Cas Number: 432037-57-5

PubChem CID: 9961434

Product Number: T651316, Order Now?

Max Phase: Phase

Molecular Formula: C30H43Cl2N5O8

Molecular Weight: 637.15

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Teglarinad chloride | EB-1627 | EB1627 | GMX-1777 | GMX1777 | Teglarinad chloride|432037-57-5|GMX1777|Teglarinad (chloride)|EB1627|1-[[[[2-[2-[2-[2-Methoxyethoxy]ethoxy]ethoxy]ethoxy]carbonyl]oxy]methyl]-4-[N'-cyano-N''-[6-[4-chlorophenoxy]hexyl]guanidino]pyridinium chloride|GMX-1777 chloride|D6V5QYX9MZ|432037-57-5 (chloride)|GMX-1777|EB-1627|[4-[[N'-[6-(4-chlorophenoxy)hexyl]-N-cyanocarbamimidoyl]amino]pyridin-1-ium-1-yl]methyl 2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethyl carbonate chloride|UNIShow More⌵

Canonical SMILES:  COCCOCCOCCOCCOC(=O)OC[n+]1ccc(N/C(=N/C#N)NCCCCCCOc2ccc(Cl)cc2)cc1.[Cl-]

Standard InChI:  InChI=1S/C30H42ClN5O8.ClH/c1-38-16-17-39-18-19-40-20-21-41-22-23-43-30(37)44-25-36-13-10-27(11-14-36)35-29(34-24-32)33-12-4-2-3-5-15-42-28-8-6-26(31)7-9-28;/h6-11,13-14H,2-5,12,15-23,25H2,1H3,(H,33,34);1H

Standard InChI Key:  DAHMXVAETAAQOZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 45 45  0  0  0  0  0  0  0  0999 V2000
   -1.6367   -2.2171    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868   -1.0564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774   -1.0397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -1.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774   -0.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1190   -1.0564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6096   -1.8580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4050   -1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4551    0.1962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -2.2964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728   -1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868   -0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588   -0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914    0.2004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728    0.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588   -1.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5552   -1.0564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0479    1.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6200    0.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7619    1.4738    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.0479    0.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3214    1.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3339   -0.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6074    1.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9018   -0.1921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1439   -1.0564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7014   -1.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8475   -1.0564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9977   -1.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6096   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2692   -1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1878    0.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4299   -1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5615   -1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9832   -1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1335   -1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7117   -1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4153   -1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2755   -1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8579   -1.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3236    0.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4655   -0.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7515    0.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0376   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  5  2  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 16  1  0
 15  5  1  0
 16 13  2  0
 17 12  1  0
 18  6  1  0
 19 22  2  0
 20 26  1  0
 21 19  1  0
 22 24  1  0
 23 25  2  0
 24 20  2  0
 25 20  1  0
 26 33  1  0
 27 34  1  0
 28 36  1  0
 29 37  1  0
 30 40  1  0
 31 15  1  0
 32 18  1  0
 33 43  1  0
 34 38  1  0
 35 29  1  0
 36 32  1  0
 37 39  1  0
 38 30  1  0
 39 28  1  0
 40 35  1  0
 41 27  1  0
 42 31  1  0
 43 44  1  0
 44 45  1  0
 45 42  1  0
 14 17  2  0
 23 19  1  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: Yes

Availability: No

Prodrug: Yes

Calculated Properties

Molecular Weight: 637.15

Molecular Weight (Monoisotopic): 636.2795

AlogP: 3.91

#Rotatable Bonds: 23

Polar Surface Area: 145.77

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 1.27

CX LogP: 0.28

CX LogD: 0.28

Aromatic Rings: 2

Heavy Atoms: 44

QED Weighted: 0.03

Np Likeness Score: -0.58

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]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Galli U, Travelli C, Massarotti A, Fakhfouri G, Rahimian R, Tron GC, Genazzani AA..  (2013)  Medicinal chemistry of nicotinamide phosphoribosyltransferase (NAMPT) inhibitors.,  56  (16): [PMID:23679915] [10.1021/jm4001049]

4. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names