chlortetracycline

ID: ALA404520

Chembl Id: CHEMBL404520

Max Phase: Approved

First Approval: 1950

Molecular Formula: C22H23ClN2O8

Molecular Weight: 478.89

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Chlorotetracycline | Chlortetracycline

Synonyms from Alternative Forms(18): Chlortetracycline bisulfate | Chlortetracycline bisulphate | Chlortetracycline hydrochloride | Aureomycin monohydrochloride | Chlortetracycline hcl | Chlortetracyclini hydrochloridum | Isphamycin | NSC-13252 | Aureomicina | Aureomycin | Chlortet hcl | Fermycin | Isaphamycin | Calcium chlortetracycline | Calcium-chlortetracycline complex | Chlorotetracycline calcium salt | Chlortetracycline calcium | Chlortetracycline calcium complex

Canonical SMILES:  CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)ccc(Cl)c4[C@@](C)(O)[C@H]3C[C@@H]12

Standard InChI:  InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1

Standard InChI Key:  CYDMQBQPVICBEU-XRNKAMNCSA-N

Alternative Forms

1. Parent:

   

   ALA404520

   CHLORTETRACYCLINE

2. Alternative Forms:

   

   ALA404520

   CHLORTETRACYCLINE BISULFATE
3. 

   ALA404520

   Chlortetracycline hydrochloride
4. 

   ALA404520

   CHLORTETRACYCLINE CALCIUM

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 478.89

Molecular Weight (Monoisotopic): 478.1143

AlogP: 0.44

#Rotatable Bonds: 2

Polar Surface Area: 181.62

Molecular Species: ZWITTERION

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.64

CX Basic pKa: 8.55

CX LogP: -2.89

CX LogD: -3.33

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 1.38

References

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16. Wei L, Wasilewski E, Chakka SK, Bello AM, Moscarello MA, Kotra LP..  (2013)  Novel inhibitors of protein arginine deiminase with potential activity in multiple sclerosis animal model.,  56  (4): [PMID:23421315] [10.1021/jm301755q]

17. 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]

18. WHO Anatomical Therapeutic Chemical Classification, 

19. DrugMatrix,  [10.6019/CHEMBL3885881]

20. Unpublished dataset, 

21. Garner AL, Lorenz DA, Sandoval J, Gallagher EE, Kerk SA, Kaur T, Menon A..  (2019)  Tetracyclines as Inhibitors of Pre-microRNA Maturation: A Disconnection between RNA Binding and Inhibition.,  10  (5): [PMID:31098005] [10.1021/acsmedchemlett.9b00091]

22. 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]

23. 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]

24. 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]

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Source

Source(6):

• Scientific Literature
• Clinical Candidates
• DrugMatrix
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6