2-hydroxy-1-naphthaldehyde 4-(1-benzylpiperidin-4-yl)thiosemicarbazone

ID: ALA4171426

PubChem CID: 145420209

Max Phase: Preclinical

Molecular Formula: C24H26N4OS

Molecular Weight: 418.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc2ccccc2c1/C=N/NC(=S)NC1CCN(Cc2ccccc2)CC1

Standard InChI:  InChI=1S/C24H26N4OS/c29-23-11-10-19-8-4-5-9-21(19)22(23)16-25-27-24(30)26-20-12-14-28(15-13-20)17-18-6-2-1-3-7-18/h1-11,16,20,29H,12-15,17H2,(H2,26,27,30)/b25-16+

Standard InChI Key:  RDBRSAOTHJRFPX-PCLIKHOPSA-N

Molfile:  

     RDKit          2D

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   35.5159  -14.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2308  -14.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9472  -14.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9444  -13.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2289  -13.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8011  -14.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0869  -14.3061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0915  -13.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3815  -13.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   33.3762  -14.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9515  -13.0565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2351  -13.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5225  -13.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2314  -14.2908    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.8061  -13.4593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0936  -13.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3771  -13.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9470  -14.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6647  -14.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3776  -14.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0920  -14.6862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9513  -13.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6661  -13.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6707  -12.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9615  -11.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2459  -12.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2446  -13.0315    0.0000 C   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 26  2  0
 25 21  2  0
 21 22  1  0
 22 23  2  0
 23 20  1  0
 23 24  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4171426

   ---

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: 418.57

Molecular Weight (Monoisotopic): 418.1827

AlogP: 4.01

#Rotatable Bonds: 5

Polar Surface Area: 59.89

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.80

CX Basic pKa: 8.18

CX LogP: 3.68

CX LogD: 3.26

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.33

Np Likeness Score: -1.39

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