trans-[3-(1,3-Benzodioxol-5-yl)prop-2-en-1-ylidene]-6-chloro-1,3-benzothiazol-2-amine

ID: ALA2296045

PubChem CID: 76309405

Max Phase: Preclinical

Molecular Formula: C17H11ClN2O2S

Molecular Weight: 342.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc2nc(/N=C/C=C/c3ccc4c(c3)OCO4)sc2c1

Standard InChI:  InChI=1S/C17H11ClN2O2S/c18-12-4-5-13-16(9-12)23-17(20-13)19-7-1-2-11-3-6-14-15(8-11)22-10-21-14/h1-9H,10H2/b2-1+,19-7+

Standard InChI Key:  XHUHFSYRFSLCBV-HVCOGCEVSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    9.8225  -23.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5322  -22.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5294  -22.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8207  -21.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2355  -21.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9448  -22.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6509  -21.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1145  -22.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1157  -22.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3352  -21.7994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8515  -22.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3332  -23.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6479  -20.8185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3540  -20.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1003  -20.7335    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.4349  -19.5909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2335  -19.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6406  -20.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4544  -20.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8621  -19.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4501  -18.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6376  -18.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6793  -19.4169    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  9  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  7 13  2  0
 13 14  1  0
 14 15  1  0
 15 18  1  0
 17 16  1  0
 16 14  2  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296045

   (E,E)-3-(1,3-benzodioxol-5-yl)-N-(6-chloro-1,3-benzothiazol-2-yl)prop-2-en-1-imine

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: 342.81

Molecular Weight (Monoisotopic): 342.0230

AlogP: 5.09

#Rotatable Bonds: 3

Polar Surface Area: 43.71

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.40

CX LogP: 5.19

CX LogD: 5.19

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: -1.16

References

1. Sharma UK, Sood S, Sharma N, Rahi P, Kumar R, Sinha AK, Gulati A.  (2013)  Synthesis and SAR investigation of natural phenylpropene-derived methoxylated cinnamaldehydes and their novel Schiff bases as potent antimicrobial and antioxidant agents,  22  (11): [10.1007/s00044-013-0484-9]

Source

Source(1):

• Scientific Literature