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

ID: ALA2296043

PubChem CID: 76323980

Max Phase: Preclinical

Molecular Formula: C13H10N2O2S

Molecular Weight: 258.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C(=C/c1ccc2c(c1)OCO2)\C=N\c1nccs1

Standard InChI:  InChI=1S/C13H10N2O2S/c1(5-14-13-15-6-7-18-13)2-10-3-4-11-12(8-10)17-9-16-11/h1-8H,9H2/b2-1+,14-5+

Standard InChI Key:  LWMFJYWKYXPEGM-SFNNOLORSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   36.6495  -16.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3592  -16.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3563  -15.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6477  -15.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0625  -15.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7718  -15.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4779  -15.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9415  -16.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9427  -15.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1622  -15.3981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6785  -16.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1602  -16.7266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.4748  -14.4172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.1810  -14.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9273  -14.3321    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   41.4718  -13.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0605  -13.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2619  -13.1896    0.0000 N   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 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296043

   (E,E)-3-(1,3-benzodioxol-5-yl)-N-(1,3-thiazol-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: 258.30

Molecular Weight (Monoisotopic): 258.0463

AlogP: 3.29

#Rotatable Bonds: 3

Polar Surface Area: 43.71

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.67

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.79

Np Likeness Score: -0.69

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