3-(5-((3-(3-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid

ID: ALA2295992

Cas Number: 6237-83-8

PubChem CID: 1901900

Max Phase: Preclinical

Molecular Formula: C22H16N4O5S2

Molecular Weight: 480.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCN1C(=O)/C(=C/c2cn(-c3ccccc3)nc2-c2cccc([N+](=O)[O-])c2)SC1=S

Standard InChI:  InChI=1S/C22H16N4O5S2/c27-19(28)9-10-24-21(29)18(33-22(24)32)12-15-13-25(16-6-2-1-3-7-16)23-20(15)14-5-4-8-17(11-14)26(30)31/h1-8,11-13H,9-10H2,(H,27,28)/b18-12-

Standard InChI Key:  RXSFNMIIAHCXFZ-PDGQHHTCSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   29.7986   -2.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6199   -2.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8784   -1.2539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2113   -0.7677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5484   -1.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3174   -2.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6488   -3.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2410   -4.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7870   -4.7671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5382   -4.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4537   -3.6187    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.4241   -4.2435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2495   -4.8451    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.6161   -5.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8344   -5.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6635   -6.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8832   -6.8828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2756   -7.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6563   -1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2627   -1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0438   -1.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2154   -0.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6040    0.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8253   -0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7692   -1.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6000   -0.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8194    0.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2073   -0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3810   -1.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1614   -1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7745   -1.8581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9476   -2.6609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9922   -1.6087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  1  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
  8 12  2  0
 10 13  2  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  3 19  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
  5 25  1  0
 31 32  2  0
 31 33  1  0
 29 31  1  0
M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2295992

   3-[(5Z)-5-[[3-(3-nitrophenyl)-1-phenylpyrazol-4-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid

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: 480.53

Molecular Weight (Monoisotopic): 480.0562

AlogP: 4.12

#Rotatable Bonds: 7

Polar Surface Area: 118.57

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.01

CX Basic pKa: 1.17

CX LogP: 4.74

CX LogD: 1.58

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: -2.22

References

1. Park H, Kyung A, Lee H, Kang S, Yoon T, Ryu SE, Jeong DG.  (2013)  Virtual screening and biochemical evaluation of the inhibitors of dual-specificity phosphatase 26,  22  (8): [10.1007/s00044-012-0405-3]

Source

Source(1):

• Scientific Literature