8-Hydroxy-2-quinolinecarboxaldehyde 4-(1-benzylpiperidin-4-yl)thiosemicarbazone

ID: ALA4175281

PubChem CID: 145420206

Max Phase: Preclinical

Molecular Formula: C23H25N5OS

Molecular Weight: 419.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1cccc2ccc(/C=N/NC(=S)NC3CCN(Cc4ccccc4)CC3)nc12

Standard InChI:  InChI=1S/C23H25N5OS/c29-21-8-4-7-18-9-10-20(25-22(18)21)15-24-27-23(30)26-19-11-13-28(14-12-19)16-17-5-2-1-3-6-17/h1-10,15,19,29H,11-14,16H2,(H2,26,27,30)/b24-15+

Standard InChI Key:  DANWBHNRDPFKOO-BUVRLJJBSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   11.7103   -8.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7092   -8.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4240   -9.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1404   -8.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1376   -8.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4221   -7.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9944   -9.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2804   -8.9965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2849   -8.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5750   -7.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8578   -8.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8552   -8.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5697   -9.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1453   -7.7471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4290   -8.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7165   -7.7405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4252   -8.9812    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0001   -8.1498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876   -7.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5713   -8.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613   -7.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1455   -8.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717   -8.9639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8588   -9.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453   -8.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -9.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4278  -10.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1461  -10.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8580  -10.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5725  -10.6087    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
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175281

   ---

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: 419.55

Molecular Weight (Monoisotopic): 419.1780

AlogP: 3.40

#Rotatable Bonds: 5

Polar Surface Area: 72.78

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.32

CX Basic pKa: 8.36

CX LogP: 3.89

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.33

Np Likeness Score: -1.52

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