(2Z,5Z)-2-{[4-(Adamantan-1-yl)-1,3-thiazol-2-yl]imino}-5-(4-nitrobenzylidene)-1,3-thiazolidin-4-one

ID: ALA602042

PubChem CID: 136066062

Max Phase: Preclinical

Molecular Formula: C23H22N4O3S2

Molecular Weight: 466.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1N/C(=N/c2nc(C34CC5CC(CC(C5)C3)C4)cs2)S/C1=C\c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C23H22N4O3S2/c28-20-18(8-13-1-3-17(4-2-13)27(29)30)32-22(25-20)26-21-24-19(12-31-21)23-9-14-5-15(10-23)7-16(6-14)11-23/h1-4,8,12,14-16H,5-7,9-11H2,(H,24,25,26,28)/b18-8-

Standard InChI Key:  PHAJATNLKDXOAS-LSCVHKIXSA-N

Molfile:  

     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
    3.2433   -4.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081   -5.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7836   -5.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994   -5.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0174   -5.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0580   -6.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3434   -6.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3594   -6.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -6.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920   -7.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2919   -8.8026    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9554   -8.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6852   -7.5202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562   -7.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138   -8.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6658   -8.7235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3840   -8.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0563   -8.8023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7198   -8.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4586   -7.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6337   -7.5362    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5065   -8.5607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9319   -6.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5836   -6.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9868   -5.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5618   -4.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7360   -4.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3372   -5.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7646   -6.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3082   -3.9832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4833   -3.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7063   -3.2606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 11  1  0
 14  8  1  0
  4  6  1  0
 12 16  1  0
  5  6  1  0
 16 17  2  0
 17 18  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 10  8  1  0
 19 22  2  0
  8  9  1  0
 20 23  2  0
 12 13  2  0
 23 24  1  0
 24 25  2  0
  1  2  1  0
 25 26  1  0
  1  3  1  0
 26 27  2  0
  2  4  1  0
 27 28  1  0
  3  5  1  0
 28 29  2  0
 29 24  1  0
 11 12  1  0
 13 14  1  0
 14 15  2  0
 30 31  2  0
 30 32  1  0
 27 30  1  0
M  CHG  2  30   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA602042

   ---

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: 466.59

Molecular Weight (Monoisotopic): 466.1133

AlogP: 5.41

#Rotatable Bonds: 4

Polar Surface Area: 97.49

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.62

CX Basic pKa: ┄

CX LogP: 5.93

CX LogD: 5.93

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.37

Np Likeness Score: -1.35

References

1. Omar K, Geronikaki A, Zoumpoulakis P, Camoutsis C, Soković M, Cirić A, Glamoclija J..  (2010)  Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs.,  18  (1): [PMID:19914077] [10.1016/j.bmc.2009.10.041]

Source

Source(1):

• Scientific Literature