(Z)-5-(4-((1-(2-(4-chlorophenyl)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methoxy)benzylidene)thiazolidine-2,4-dione

ID: ALA4521668

PubChem CID: 155542709

Max Phase: Preclinical

Molecular Formula: C21H15ClN4O4S

Molecular Weight: 454.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)/C(=C/c2ccc(OCc3cn(CC(=O)c4ccc(Cl)cc4)nn3)cc2)S1

Standard InChI:  InChI=1S/C21H15ClN4O4S/c22-15-5-3-14(4-6-15)18(27)11-26-10-16(24-25-26)12-30-17-7-1-13(2-8-17)9-19-20(28)23-21(29)31-19/h1-10H,11-12H2,(H,23,28,29)/b19-9-

Standard InChI Key:  LIBPWQBUQQENPS-OCKHKDLRSA-N

Molfile:  

 
     RDKit          2D

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   36.1700   -5.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3205   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3164   -3.0339    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   43.0923   -3.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5761   -2.6316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.0990   -1.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4920   -2.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4909   -3.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1989   -3.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9086   -3.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9058   -2.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1971   -1.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6119   -1.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3409   -4.0689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.3555   -1.1923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7829   -3.4521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0755   -3.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3597   -4.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3713   -3.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5979   -3.1869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1082   -3.8411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5786   -4.5095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3528   -5.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9441   -5.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9442   -4.5094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1282   -5.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7196   -6.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1282   -7.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9496   -7.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3545   -6.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7205   -8.0469    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
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 11 12  2  0
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 11 13  1  0
 13  2  2  0
  4 14  2  0
  6 15  2  0
  8 16  1  0
 16 17  1  0
 17 19  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
 22  1  1  0
  1 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 24  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521668

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 454.90

Molecular Weight (Monoisotopic): 454.0503

AlogP: 3.72

#Rotatable Bonds: 7

Polar Surface Area: 103.18

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.20

CX Basic pKa: ┄

CX LogP: 3.38

CX LogD: 2.23

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -1.79

References

1. Elzahhar PA, Alaaeddine R, Ibrahim TM, Nassra R, Ismail A, Chua BSK, Frkic RL, Bruning JB, Wallner N, Knape T, von Knethen A, Labib H, El-Yazbi AF, Belal ASF..  (2019)  Shooting three inflammatory targets with a single bullet: Novel multi-targeting anti-inflammatory glitazones.,  167  [PMID:30818268] [10.1016/j.ejmech.2019.02.034]

Source

Source(1):

• Scientific Literature