2,3,4-Trihydroxybenzaldehyde 4-(1-benzylpiperidin-4-yl)thiosemicarbazone

ID: ALA4162052

PubChem CID: 145420213

Max Phase: Preclinical

Molecular Formula: C20H24N4O3S

Molecular Weight: 400.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(/C=N/NC(=S)NC2CCN(Cc3ccccc3)CC2)c(O)c1O

Standard InChI:  InChI=1S/C20H24N4O3S/c25-17-7-6-15(18(26)19(17)27)12-21-23-20(28)22-16-8-10-24(11-9-16)13-14-4-2-1-3-5-14/h1-7,12,16,25-27H,8-11,13H2,(H2,22,23,28)/b21-12+

Standard InChI Key:  HUHULDXUTKOREG-CIAFOILYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   11.8694  -20.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8682  -21.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5830  -21.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2994  -21.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2966  -20.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5812  -20.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1534  -21.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4393  -21.5469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4439  -20.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7339  -20.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0166  -20.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0140  -21.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7285  -21.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3041  -20.2974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5877  -20.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8751  -20.2909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5839  -21.5316    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1588  -20.7001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462  -20.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298  -20.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198  -20.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3040  -20.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7303  -21.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174  -21.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3038  -21.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447  -21.9269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0153  -22.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5884  -21.9202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 25  2  0
 24 23  2  0
 23 20  1  0
 24 25  1  0
 23 26  1  0
 24 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4162052

   ---

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: 400.50

Molecular Weight (Monoisotopic): 400.1569

AlogP: 2.27

#Rotatable Bonds: 5

Polar Surface Area: 100.35

Molecular Species: BASE

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.17

CX Basic pKa: 8.78

CX LogP: 2.08

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.23

Np Likeness Score: -1.23

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