(E)-1-(2-(Ethylamino)-4-methylthiazol-5-yl)-3-(4-nitrophenyl)prop-2-en-1-one

ID: ALA1926920

PubChem CID: 57392304

Max Phase: Preclinical

Molecular Formula: C15H15N3O3S

Molecular Weight: 317.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNc1nc(C)c(C(=O)/C=C/c2ccc([N+](=O)[O-])cc2)s1

Standard InChI:  InChI=1S/C15H15N3O3S/c1-3-16-15-17-10(2)14(22-15)13(19)9-6-11-4-7-12(8-5-11)18(20)21/h4-9H,3H2,1-2H3,(H,16,17)/b9-6+

Standard InChI Key:  OCJJFIFIUZJWSX-RMKNXTFCSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   22.2486   -4.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2474   -4.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9622   -5.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6787   -4.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6758   -4.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9604   -3.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5326   -5.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8185   -4.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1037   -5.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3895   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1030   -6.1548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3087   -4.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5018   -3.9258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0887   -4.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6404   -5.2534    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9237   -3.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2682   -4.7257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7837   -4.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9632   -4.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3909   -3.6714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3878   -2.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1069   -4.0812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0
 10 12  2  0
  5  6  2  0
  6  1  1  0
  1  2  2  0
  2  7  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 10  1  0
  3  4  2  0
 12 16  1  0
  7  8  2  0
 14 17  1  0
 17 18  1  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
  9 10  1  0
  2  3  1  0
 20 21  2  0
 20 22  1  0
  5 20  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1926920

   (E)-1-[2-(ethylamino)-4-methyl-1,3-thiazol-5-yl]-3-(4-nitrophenyl)prop-2-en-1-one

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: 317.37

Molecular Weight (Monoisotopic): 317.0834

AlogP: 3.69

#Rotatable Bonds: 6

Polar Surface Area: 85.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.26

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: -1.52

References

1. Liaras K, Geronikaki A, Glamočlija J, Cirić A, Soković M..  (2011)  Novel (E)-1-(4-methyl-2-(alkylamino)thiazol-5-yl)-3-arylprop-2-en-1-ones as potent antimicrobial agents.,  19  (24): [PMID:22079864] [10.1016/j.bmc.2011.10.059]

Source

Source(1):

• Scientific Literature