(E)-3-(2-((4-oxothiazolidin-2-ylidene)methyl)-4-(pyridin-2-yl)thiazol-5-yl)propanoic acid

ID: ALA2348091

PubChem CID: 136219141

Max Phase: Preclinical

Molecular Formula: C15H13N3O3S2

Molecular Weight: 347.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1sc(/C=C2\NC(=O)CS2)nc1-c1ccccn1

Standard InChI:  InChI=1S/C15H13N3O3S2/c19-11-8-22-12(17-11)7-13-18-15(9-3-1-2-6-16-9)10(23-13)4-5-14(20)21/h1-3,6-7H,4-5,8H2,(H,17,19)(H,20,21)/b12-7+

Standard InChI Key:  FXCKSJPZDBQRLO-KPKJPENVSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   22.2416   -3.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4199   -3.9827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1659   -4.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8307   -5.2473    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.4955   -4.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7183   -3.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5320   -3.4113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0122   -2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6799   -2.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8627   -1.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3861   -2.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3887   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7815   -4.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8714   -3.6573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1249   -3.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5780   -3.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9867   -4.6398    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9551   -2.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2726   -5.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4425   -5.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2197   -6.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3906   -6.8689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8281   -5.5228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  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
  1  6  1  0
  3 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 15 18  2  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2348091

   ---

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: 347.42

Molecular Weight (Monoisotopic): 347.0398

AlogP: 2.38

#Rotatable Bonds: 5

Polar Surface Area: 92.18

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.32

CX Basic pKa: 0.88

CX LogP: 2.17

CX LogD: -0.78

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.86

Np Likeness Score: -0.66

References

1. Atobe M, Maekawara N, Ishiguro N, Sogame S, Suenaga Y, Kawanishi M, Suzuki H, Jinno N, Tanaka E, Miyoshi S..  (2013)  A series of thiazole derivatives bearing thiazolidin-4-one as non-competitive ADAMTS-5 (aggrecanase-2) inhibitors.,  23  (7): [PMID:23453070] [10.1016/j.bmcl.2013.01.121]

2. Sogame S, Suenaga Y, Atobe M, Kawanishi M, Tanaka E, Miyoshi S..  (2014)  Discovery of a benzimidazole series of ADAMTS-5 (aggrecanase-2) inhibitors by scaffold hopping.,  71  [PMID:24316668] [10.1016/j.ejmech.2013.10.075]

Source

Source(1):

• Scientific Literature