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

ID: ALA4475190

PubChem CID: 155537482

Max Phase: Preclinical

Molecular Formula: C20H15BrN4O3S

Molecular Weight: 471.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)/C(=C/c2ccc(OCc3cn(Cc4ccc(Br)cc4)nn3)cc2)S1

Standard InChI:  InChI=1S/C20H15BrN4O3S/c21-15-5-1-14(2-6-15)10-25-11-16(23-24-25)12-28-17-7-3-13(4-8-17)9-18-19(26)22-20(27)29-18/h1-9,11H,10,12H2,(H,22,26,27)/b18-9-

Standard InChI Key:  UOCHXCVPYZVORD-NVMNQCDNSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   23.0051  -11.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0010  -12.0519    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.7769  -12.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2607  -11.6496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7836  -10.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1766  -11.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1755  -12.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8835  -12.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5932  -12.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5903  -11.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8817  -10.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2965  -10.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0255  -13.0868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0400  -10.2102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4674  -12.4701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7600  -12.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0442  -13.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0559  -12.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2825  -12.2049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7928  -12.8591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2632  -13.5275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8545  -14.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0373  -14.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6304  -13.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8139  -13.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4045  -14.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8174  -14.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6325  -14.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5873  -14.2355    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 10 12  1  0
 12  1  2  0
  3 13  2  0
  5 14  2  0
  7 15  1  0
 15 16  1  0
 16 18  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475190

   ---

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: 471.34

Molecular Weight (Monoisotopic): 470.0048

AlogP: 3.99

#Rotatable Bonds: 6

Polar Surface Area: 86.11

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.20

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 2.89

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -1.80

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