ID: ALA1908355

Max Phase: Phase

Molecular Formula: C14H9ClN2O3S

Molecular Weight: 320.76

Molecule Type: Small molecule

Representations

Synonyms (3): Tenidap | CP-66,248 | CP-66248
Synonyms from Alternative Forms(3):

Canonical SMILES:  NC(=O)N1C(=O)/C(=C(\O)c2cccs2)c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C14H9ClN2O3S/c15-7-3-4-9-8(6-7)11(13(19)17(9)14(16)20)12(18)10-2-1-5-21-10/h1-6,18H,(H2,16,20)/b12-11-

Standard InChI Key:  LXIKEPCNDFVJKC-QXMHVHEDSA-N

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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 320.76

Molecular Weight (Monoisotopic): 320.0022

AlogP: 3.25

#Rotatable Bonds: 1

Polar Surface Area: 83.63

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.83

CX Basic pKa:

CX LogP: 2.32

CX LogD: -0.06

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.62

Np Likeness Score: -1.17

References

1. Mylari BL, Carty TJ, Moore PF, Zembrowski WJ..  (1990)  1,2-Dihydro-1-oxopyrrolo[3,2,1-kl]phenothiazine-2-carboxamides and congeners, dual cyclooxygenase/5-lipoxygenase inhibitors with antiinflammatory activity.,  33  (7): [PMID:2113951] [10.1021/jm00169a035]

2. Inagaki M, Tsuri T, Jyoyama H, Ono T, Yamada K, Kobayashi M, Hori Y, Arimura A, Yasui K, Ohno K, Kakudo S, Koizumi K, Suzuki R, Kawai S, Kato M, Matsumoto S..  (2000)  Novel antiarthritic agents with 1,2-isothiazolidine-1,1-dioxide (gamma-sultam) skeleton: cytokine suppressive dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase.,  43  (10): [PMID:10821716] [10.1021/jm9906015]

3. Suzuki F, Kuroda T, Tamura T, Sato S, Ohmori K, Ichikawa S..  (1992)  New antiinflammatory agents. 2. 5-Phenyl-3H-imidazo[4,5-c][1,8]naphthyridin-4(5H)-ones: a new class of nonsteroidal antiinflammatory agents with potent activity like glucocorticoids.,  35  (15): [PMID:1495017] [10.1021/jm00093a020]

4. Guerra A, Campillo NE, Páez JA..  (2010)  Neural computational prediction of oral drug absorption based on CODES 2D descriptors.,  45  (3): [PMID:20022146] [10.1016/j.ejmech.2009.11.034]

5. Lai Y, Ma L, Huang W, Yu X, Zhang Y, Ji H, Tian J..  (2010)  Synthesis and biological evaluation of 3-[4-(amino/methylsulfonyl)phenyl]methylene-indolin-2-one derivatives as novel COX-1/2 and 5-LOX inhibitors.,  20  (24): [PMID:21055929] [10.1016/j.bmcl.2010.10.056]

6. Talevi A, Goodarzi M, Ortiz EV, Duchowicz PR, Bellera CL, Pesce G, Castro EA, Bruno-Blanch LE..  (2011)  Prediction of drug intestinal absorption by new linear and non-linear QSPR.,  46  (1): [PMID:21112128] [10.1016/j.ejmech.2010.11.005]

7. Gozalbes R, Jacewicz M, Annand R, Tsaioun K, Pineda-Lucena A..  (2011)  QSAR-based permeability model for drug-like compounds.,  19  (8): [PMID:21458999] [10.1016/j.bmc.2011.03.011]

8. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

9. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

10. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

11. WHO Anatomical Therapeutic Chemical Classification, 

12. DrugMatrix,  [10.6019/CHEMBL3885881]

13. Singh P, Kaur S, Sharma A, Kaur G, Bhatti R..  (2017)  TNF-α and IL-6 inhibitors: Conjugates of N-substituted indole and aminophenylmorpholin-3-one as anti-inflammatory agents.,  140  [PMID:28923390] [10.1016/j.ejmech.2017.09.003]

14. 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]

15. 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]

16. 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]

17. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

18. 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]

Source

Source(7):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6