(E)-2-(2-((4-oxothiazolidin-2-ylidene)methyl)-4-phenylthiazol-5-yl)acetic acid

ID: ALA2347847

PubChem CID: 136219136

Max Phase: Preclinical

Molecular Formula: C15H12N2O3S2

Molecular Weight: 332.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1sc(/C=C2\NC(=O)CS2)nc1-c1ccccc1

Standard InChI:  InChI=1S/C15H12N2O3S2/c18-11-8-21-12(16-11)7-13-17-15(9-4-2-1-3-5-9)10(22-13)6-14(19)20/h1-5,7H,6,8H2,(H,16,18)(H,19,20)/b12-7+

Standard InChI Key:  JFYUPKXGFNQNTK-KPKJPENVSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    4.5936   -3.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7719   -3.3389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5179   -4.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1827   -4.6035    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8474   -4.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0703   -2.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8839   -2.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3641   -2.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0319   -1.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2147   -1.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7381   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6246   -4.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7945   -5.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1893   -5.7206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5738   -5.4263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407   -4.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1334   -3.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2234   -3.0134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769   -2.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9300   -3.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3386   -3.9959    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -1.8816    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
  5 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  3 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 19 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2347847

   ---

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: 332.41

Molecular Weight (Monoisotopic): 332.0289

AlogP: 2.60

#Rotatable Bonds: 4

Polar Surface Area: 79.29

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.46

CX Basic pKa: 1.17

CX LogP: 2.56

CX LogD: -0.29

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.90

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]

Source

Source(1):

• Scientific Literature