pyridoxal 4-N-(1-benzylpiperidin-4-yl)thiosemicarbazone hydrochloride

ID: ALA4174866

PubChem CID: 145949990

Max Phase: Preclinical

Molecular Formula: C21H28ClN5O2S

Molecular Weight: 413.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncc(CO)c(/C=N/NC(=S)NC2CCN(Cc3ccccc3)CC2)c1O.Cl

Standard InChI:  InChI=1S/C21H27N5O2S.ClH/c1-15-20(28)19(17(14-27)11-22-15)12-23-25-21(29)24-18-7-9-26(10-8-18)13-16-5-3-2-4-6-16;/h2-6,11-12,18,27-28H,7-10,13-14H2,1H3,(H2,24,25,29);1H/b23-12+;

Standard InChI Key:  FIBAEABKNXBHRO-RRHSQXQGSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   30.2304   -4.5375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.5815   -2.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5804   -3.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2951   -3.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0116   -3.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0087   -2.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2933   -2.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8655   -3.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1515   -3.5179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1560   -2.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4460   -2.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7288   -2.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7262   -3.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4408   -3.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0162   -2.2683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2999   -2.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5873   -2.2618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2961   -3.5025    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.8710   -2.6711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1584   -2.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4421   -2.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7321   -2.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0162   -2.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0120   -3.4806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7296   -3.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4425   -3.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7287   -4.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1570   -3.8979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7377   -1.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0262   -1.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 25 27  1  0
 26 28  1  0
 22 29  1  0
 29 30  1  0
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: 413.55

Molecular Weight (Monoisotopic): 413.1885

AlogP: 2.05

#Rotatable Bonds: 6

Polar Surface Area: 93.01

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.07

CX Basic pKa: 8.67

CX LogP: 0.82

CX LogD: 0.44

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: -1.37

References

1. Palanimuthu D, Poon R, Sahni S, Anjum R, Hibbs D, Lin HY, Bernhardt PV, Kalinowski DS, Richardson DR..  (2017)  A novel class of thiosemicarbazones show multi-functional activity for the treatment of Alzheimer's disease.,  139  [PMID:28841514] [10.1016/j.ejmech.2017.08.021]

Source

Source(1):

• Scientific Literature