2-hydroxy-5-(2-hydroxy-3,5-dinitrobenzylidene)-3-phenylthiazolidin-4-one

ID: ALA3343828

PubChem CID: 5969872

Max Phase: Preclinical

Molecular Formula: C16H9N3O7S

Molecular Weight: 387.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1S/C(=C/c2cc([N+](=O)[O-])cc([N+](=O)[O-])c2O)C(=O)N1c1ccccc1

Standard InChI:  InChI=1S/C16H9N3O7S/c20-14-9(6-11(18(23)24)8-12(14)19(25)26)7-13-15(21)17(16(22)27-13)10-4-2-1-3-5-10/h1-8,20H/b13-7+

Standard InChI Key:  UHDOGMFMIUYZPC-NTUHNPAUSA-N

Molfile:  

     RDKit          2D

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   16.5276  -21.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5265  -21.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2413  -22.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9578  -21.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9548  -21.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2395  -20.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2355  -19.8397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5198  -19.4293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9487  -19.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6753  -22.3209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3891  -21.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6766  -23.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2411  -23.1484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8117  -22.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0975  -21.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0109  -21.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2041  -20.9189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7909  -21.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3426  -22.2464    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.6240  -20.5390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9704  -21.7187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8691  -20.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3579  -19.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0236  -18.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2024  -18.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7165  -19.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0535  -20.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  7  9  1  0
  6  7  1  0
 10 11  2  0
 10 12  1  0
  4 10  1  0
  3 13  1  0
  2 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 16 20  2  0
 18 21  2  0
 17 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  CHG  4   7   1   9  -1  10   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3343828

   (5E)-5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione

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: 387.33

Molecular Weight (Monoisotopic): 387.0161

AlogP: 3.45

#Rotatable Bonds: 4

Polar Surface Area: 143.89

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.30

CX Basic pKa: ┄

CX LogP: 3.31

CX LogD: 1.39

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: -1.63

References

1. Meneely KM, Luo Q, Riley AP, Taylor B, Roy A, Stein RL, Prisinzano TE, Lamb AL..  (2014)  Expanding the results of a high throughput screen against an isochorismate-pyruvate lyase to enzymes of a similar scaffold or mechanism.,  22  (21): [PMID:25282647] [10.1016/j.bmc.2014.09.010]

Source

Source(1):

• Scientific Literature