2-Cyano-3-(3,4-dihydroxy-phenyl)-acrylic acid 2-thiophen-2-yl-ethyl ester

ID: ALA37081

Cas Number: 132465-10-2

PubChem CID: 6069552

Product Number: T288932, Order Now?

Max Phase: Preclinical

Molecular Formula: C16H13NO4S

Molecular Weight: 315.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C\c1ccc(O)c(O)c1)C(=O)OCCc1cccs1

Standard InChI:  InChI=1S/C16H13NO4S/c17-10-12(8-11-3-4-14(18)15(19)9-11)16(20)21-6-5-13-2-1-7-22-13/h1-4,7-9,18-19H,5-6H2/b12-8+

Standard InChI Key:  KCGLTUBCAGZLHP-XYOKQWHBSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    4.5417   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -2.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -6.9125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -7.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -7.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -4.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -8.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -8.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -5.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -2.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9667   -3.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  4  3  0
  6  7  1  0
  7 18  1  0
  8 11  2  0
  9  2  1  0
 10 16  2  0
 11  9  1  0
 12  6  1  0
 13  3  2  0
 14  7  2  0
 15 14  1  0
 16 19  1  0
 17  3  1  0
 18 22  1  0
 19  9  2  0
 20  8  1  0
 21 10  1  0
 22 17  1  0
 10  8  1  0
 15 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA37081

   2-TEDC

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: 315.35

Molecular Weight (Monoisotopic): 315.0565

AlogP: 2.85

#Rotatable Bonds: 5

Polar Surface Area: 90.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.41

CX Basic pKa: ┄

CX LogP: 3.65

CX LogD: 3.61

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: -0.86

References

1. Cho H, Ueda M, Tamaoka M, Hamaguchi M, Aisaka K, Kiso Y, Inoue T, Ogino R, Tatsuoka T, Ishihara T..  (1991)  Novel caffeic acid derivatives: extremely potent inhibitors of 12-lipoxygenase.,  34  (4): [PMID:2016727] [10.1021/jm00108a039]

2. PubChem BioAssay data set, 

3. Vivier D, Bennis K, Lesage F, Ducki S..  (2016)  Perspectives on the Two-Pore Domain Potassium Channel TREK-1 (TWIK-Related K(+) Channel 1). A Novel Therapeutic Target?,  59  (11): [PMID:26588045] [10.1021/acs.jmedchem.5b00671]

4. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

5. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

6. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

7. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

8. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - IncuCyte,  [10.6019/CHEMBL5303304]

9. EUbOPEN.  (2023)  Tm Shift (DSF) assay results for EUbOPEN Chemogenomics Library,  [10.6019/CHEMBL5308504]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21
• EUbOPEN Chemogenomic Library
• Fraunhofer HDAC6