ID: ALA292687

Max Phase: Phase

Molecular Formula: C6H3ClN2O4

Molecular Weight: 202.55

Molecule Type: Small molecule

Representations

Synonyms (3): 1-chloro-2,4-dinitrobenzene | Dinitrochlorobenzene | NSC-6292
Synonyms from Alternative Forms(3):

Canonical SMILES:  O=[N+]([O-])c1ccc(Cl)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H

Standard InChI Key:  VYZAHLCBVHPDDF-UHFFFAOYSA-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: 202.55

Molecular Weight (Monoisotopic): 201.9781

AlogP: 2.16

#Rotatable Bonds: 2

Polar Surface Area: 86.28

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.46

CX LogD: 2.46

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.54

Np Likeness Score: -1.90

References

1. Sugiyama N, Akahoshi F, Kuwahara S, Kajii M, Sakaue Y, Yakumaru H, Sugiura M, Fukaya C..  (1994)  Synthesis and topical antiinflammatory and antiallergic activities of antioxidant o-aminophenol derivatives.,  37  (13): [PMID:7913134] [10.1021/jm00039a010]

2. Debnath AK, Lopez de Compadre RL, Debnath G, Shusterman AJ, Hansch C..  (1991)  Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity.,  34  (2): [PMID:1995902] [10.1021/jm00106a046]

3. Shami PJ, Saavedra JE, Bonifant CL, Chu J, Udupi V, Malaviya S, Carr BI, Kar S, Wang M, Jia L, Ji X, Keefer LK..  (2006)  Antitumor activity of JS-K [O2-(2,4-dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and related O2-aryl diazeniumdiolates in vitro and in vivo.,  49  (14): [PMID:16821795] [10.1021/jm060022h]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. Malwal SR, Sriram D, Yogeeswari P, Konkimalla VB, Chakrapani H..  (2012)  Design, synthesis, and evaluation of thiol-activated sources of sulfur dioxide (SO₂) as antimycobacterial agents.,  55  (1): [PMID:22128803] [10.1021/jm201023g]

10. PubChem BioAssay data set, 

11. PubChem BioAssay data set, 

12. Xie Y, Dahlin JL, Oakley AJ, Casarotto MG, Board PG, Baell JB..  (2018)  Reviewing Hit Discovery Literature for Difficult Targets: Glutathione Transferase Omega-1 as an Example.,  61  (17): [PMID:29652143] [10.1021/acs.jmedchem.8b00318]

13. Wilke J, Kawamura T, Watanabe N, Osada H, Ziegler S, Waldmann H..  (2018)  Identification of cytotoxic, glutathione-reactive moieties inducing accumulation of reactive oxygen species via glutathione depletion.,  26  (8): [PMID:29170028] [10.1016/j.bmc.2017.11.009]

14. Unpublished dataset, 

15. 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]

16. 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]

17. 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]

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

19. 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(6):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6