2-(-5-(-3-(furan-2-yl)allylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid

ID: ALA255881

Cas Number: 1164116-77-1

PubChem CID: 6375556

Max Phase: Preclinical

Molecular Formula: C13H11NO4S2

Molecular Weight: 309.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C(=O)O)N1C(=O)/C(=C/C=C/c2ccco2)SC1=S

Standard InChI:  InChI=1S/C13H11NO4S2/c1-8(12(16)17)14-11(15)10(20-13(14)19)6-2-4-9-5-3-7-18-9/h2-8H,1H3,(H,16,17)/b4-2+,10-6-

Standard InChI Key:  TUQJXQLTYBPFIW-QXYPORFMSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   12.9613   -2.0710    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7446   -2.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4345   -3.3189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0777   -2.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7851   -2.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9732   -3.1594    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8737   -3.0191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4744   -4.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7807   -4.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2079   -4.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2478   -5.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9016   -4.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2372   -1.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8656   -0.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3177    0.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9461    0.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3246    1.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7436    2.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0070    1.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1329    0.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 10  1  0
  5  1  1  0
 10 11  1  0
  1  2  1  0
 10 12  2  0
  2  6  2  0
  5 13  2  0
 13 14  1  0
  4  7  2  0
 14 15  2  0
  2  3  1  0
 15 16  1  0
 16 17  1  0
  3  8  1  0
  3  4  1  0
  8  9  1  0
  4  5  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA255881

   2-((Z)-5-((E)-3-(furan-2-yl)allylidene)-4-oxo-2-thioxothiazolidin-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: 309.37

Molecular Weight (Monoisotopic): 309.0129

AlogP: 2.51

#Rotatable Bonds: 4

Polar Surface Area: 70.75

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.98

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: -0.57

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.68

Np Likeness Score: -1.45

References

1. Xie Y, Liu Y, Gong G, Rinderspacher A, Deng SX, Smith DH, Toebben U, Tzilianos E, Branden L, Vidović D, Chung C, Schürer S, Tautz L, Landry DW..  (2008)  Discovery of a novel submicromolar inhibitor of the lymphoid specific tyrosine phosphatase.,  18  (9): [PMID:18434147] [10.1016/j.bmcl.2008.03.079]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays