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

ID: ALA4164649

PubChem CID: 145420207

Max Phase: Preclinical

Molecular Formula: C20H24N4O2S

Molecular Weight: 384.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1cccc(/C=N/NC(=S)NC2CCN(Cc3ccccc3)CC2)c1O

Standard InChI:  InChI=1S/C20H24N4O2S/c25-18-8-4-7-16(19(18)26)13-21-23-20(27)22-17-9-11-24(12-10-17)14-15-5-2-1-3-6-15/h1-8,13,17,25-26H,9-12,14H2,(H2,22,23,27)/b21-13+

Standard InChI Key:  KACTXBZFANXHMK-FYJGNVAPSA-N

Molfile:  

     RDKit          2D

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   11.3062  -13.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3050  -14.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0199  -15.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7362  -14.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7334  -13.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0180  -13.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5903  -15.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8762  -14.7128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8808  -13.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1709  -13.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4536  -13.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4510  -14.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1656  -15.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7411  -13.4633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0248  -13.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3123  -13.4569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0210  -14.6975    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5959  -13.8660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8834  -13.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1671  -13.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4571  -13.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7414  -13.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676  -14.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4547  -15.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7412  -14.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8819  -15.0928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4527  -15.9161    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
M  END

Alternative Forms

1. Parent:

   

   ALA4164649

   ---

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: 384.51

Molecular Weight (Monoisotopic): 384.1620

AlogP: 2.56

#Rotatable Bonds: 5

Polar Surface Area: 80.12

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.95

CX Basic pKa: 8.26

CX LogP: 2.53

CX LogD: 1.97

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.27

Np Likeness Score: -1.45

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