2-(5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid

ID: ALA2316879

PubChem CID: 5786815

Max Phase: Preclinical

Molecular Formula: C12H9NO5S2

Molecular Weight: 311.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CN1C(=O)/C(=C/c2ccc(O)c(O)c2)SC1=S

Standard InChI:  InChI=1S/C12H9NO5S2/c14-7-2-1-6(3-8(7)15)4-9-11(18)13(5-10(16)17)12(19)20-9/h1-4,14-15H,5H2,(H,16,17)/b9-4-

Standard InChI Key:  MNPZQUQRMCXSTL-WTKPLQERSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    2.7102  -10.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7090  -10.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171  -11.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1267  -10.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1239  -10.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -9.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0024   -9.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010  -11.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8351  -11.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421  -10.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2856  -11.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8314  -10.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4217   -9.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6227  -10.1559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7528   -9.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4565  -12.0990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6443  -10.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1236  -10.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9379  -10.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7915   -9.3670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  2  8  1  0
  4  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 13 15  2  0
 11 16  2  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2316879

   2-[(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic 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: 311.34

Molecular Weight (Monoisotopic): 310.9922

AlogP: 1.38

#Rotatable Bonds: 3

Polar Surface Area: 98.07

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.27

CX Basic pKa: ┄

CX LogP: 1.83

CX LogD: -1.61

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.44

Np Likeness Score: -0.99

References

1. Kohlmann A, Zech SG, Li F, Zhou T, Squillace RM, Commodore L, Greenfield MT, Lu X, Miller DP, Huang WS, Qi J, Thomas RM, Wang Y, Zhang S, Dodd R, Liu S, Xu R, Xu Y, Miret JJ, Rivera V, Clackson T, Shakespeare WC, Zhu X, Dalgarno DC..  (2013)  Fragment growing and linking lead to novel nanomolar lactate dehydrogenase inhibitors.,  56  (3): [PMID:23302067] [10.1021/jm3014844]

2. Zinglé C, Tritsch D, Grosdemange-Billiard C, Rohmer M..  (2014)  Catechol-rhodanine derivatives: Specific and promiscuous inhibitors of Escherichia coli deoxyxylulose phosphate reductoisomerase (DXR).,  22  (14): [PMID:24890653] [10.1016/j.bmc.2014.05.004]

Source

Source(1):

• Scientific Literature