3-(4-(Adamantan-1-yl)thiazol-2-yl)-2-(4-nitrophenyl)thiazolidin-4-one

ID: ALA3735844

PubChem CID: 127035258

Max Phase: Preclinical

Molecular Formula: C22H23N3O3S2

Molecular Weight: 441.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CSC(c2ccc([N+](=O)[O-])cc2)N1c1nc(C23CC4CC(CC(C4)C2)C3)cs1

Standard InChI:  InChI=1S/C22H23N3O3S2/c26-19-12-29-20(16-1-3-17(4-2-16)25(27)28)24(19)21-23-18(11-30-21)22-8-13-5-14(9-22)7-15(6-13)10-22/h1-4,11,13-15,20H,5-10,12H2

Standard InChI Key:  DCZXFQJVRGVLNP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 35  0  0  0  0  0  0  0  0999 V2000
   -4.0702    1.0031    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    1.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6682    0.9900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1118   -0.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6118   -0.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4027   -1.3986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388    3.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    4.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7038    5.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0520    6.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2955    5.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1908    4.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3710    2.7193    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2078    1.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    0.3574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1909    1.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659    2.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300    2.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5893   -0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602    2.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    2.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2034   -0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0291    0.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599    7.8670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2392    8.3915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1662    8.5398    0.0000 O   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
  1  5  1  0
  4  6  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  2  7  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 13 17  1  0
 16 18  1  0
  3 14  1  0
 19 20  1  0
 19 21  1  0
 20 22  1  0
 21 23  1  0
 22 18  1  0
 23 18  1  0
 24 25  1  0
 21 24  1  0
 20 26  1  0
 18 27  1  0
 27 25  1  0
 25 26  1  0
 28 29  2  0
 28 30  1  0
 10 28  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3735844

   ---

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: 441.58

Molecular Weight (Monoisotopic): 441.1181

AlogP: 5.30

#Rotatable Bonds: 4

Polar Surface Area: 76.34

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.20

CX LogD: 5.20

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.48

Np Likeness Score: -1.11

References

1. Pitta E, Tsolaki E, Geronikaki A, Petrovic J, Glamoclija J, Sokovic M, Crespan E, Maga G, Bhunia SS, Saxena AK.  (2015)  4-Thiazolidinone derivatives as potent antimicrobial agents: microwave-assisted synthesis, biological evaluation and docking studies,  6  (2): [10.1039/C4MD00399C]

Source

Source(1):

• Scientific Literature