(Z)-2-((5-((5-ethylfuran-2-yl)methylene)-4-oxo-4,5-dihydrothiazol-2-yl)amino)-2-(4-fluorophenyl)acetic acid

ID: ALA5279984

Max Phase: Preclinical

Molecular Formula: C18H15FN2O4S

Molecular Weight: 374.39

Names and Identifiers

Canonical SMILES:  CCc1ccc(/C=C2\SC(NC(C(=O)O)c3ccc(F)cc3)=NC2=O)o1

Standard InChI:  InChI=1S/C18H15FN2O4S/c1-2-12-7-8-13(25-12)9-14-16(22)21-18(26-14)20-15(17(23)24)10-3-5-11(19)6-4-10/h3-9,15H,2H2,1H3,(H,23,24)(H,20,21,22)/b14-9-

Standard InChI Key:  RNEACARJKXYVND-ZROIWOOFSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -2.0738    1.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4090    0.5964    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7378    1.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9890    1.8648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131    1.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2948    2.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0450    0.8161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8601    0.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0370    0.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6618    1.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    1.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    2.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6093    0.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3914    0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8395    1.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0577    1.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125    2.7200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871    2.4323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7923    0.3245    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922   -0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7114   -1.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9055   -1.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884   -0.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5749   -2.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0641   -2.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  1  0
  5  6  2  0
  3  7  1  0
  1  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 11  1  0
 12 18  2  0
 12 19  1  0
 15 20  1  0
  9 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24  9  1  0
 23 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5279984

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 374.39

Molecular Weight (Monoisotopic): 374.0737

AlogP: 3.37

#Rotatable Bonds: 5

Polar Surface Area: 91.90

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.88

CX Basic pKa: ┄

CX LogP: 3.08

CX LogD: -0.14

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: -1.40

References

1. Kaminskyy D, Kryshchyshyn A, Lesyk R..  (2017)  5-Ene-4-thiazolidinones - An efficient tool in medicinal chemistry.,  140  [PMID:28987611] [10.1016/j.ejmech.2017.09.031]

Source

Source(1):

• Scientific Literature