rel-Halofuginone

ID: ALA1199540

Chembl Id: CHEMBL1199540

Cas Number: 55837-20-2

PubChem CID: 456390

Max Phase: Preclinical

Molecular Formula: C16H17BrClN3O3

Molecular Weight: 414.69

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Halofuginone | Halofuginone|(+)-Halofuginone|Halocur|Halofuginone, (+)-|55837-20-2|6-Chloro-7-bromo-(+)-febrifugine|Halofuginon|Halofuginona|Halofuginonum|H84E4Y7HC9|L31MM1385E|(+/-)-trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3H)-quinazolinone|Halofuginone [INN:BAN]|7-Bromo-6-chloro-3-(3-((2R,3S)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3H)-quinazolinone|868851-54-1|Halofunginone|7-Bromo-6-Chloro-3-{3-[(2r,3s)-3-Hydroxypiperidin-2-Yl]-2-Oxopropyl}quinazolin-4(3h)-One|4(3H)-QuShow More⌵

Canonical SMILES:  O=C(C[C@H]1NCCC[C@@H]1O)Cn1cnc2cc(Br)c(Cl)cc2c1=O

Standard InChI:  InChI=1S/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2/t14-,15+/m1/s1

Standard InChI Key:  LVASCWIMLIKXLA-CABCVRRESA-N

Alternative Forms

1. Alternative Forms:

   

   ALA1199540

   Halocur

2. Parent:

   

   ALA1199540

   Halofuginone

Molecule Features

Natural Product: Yes

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: 414.69

Molecular Weight (Monoisotopic): 413.0142

AlogP: 1.88

#Rotatable Bonds: 4

Polar Surface Area: 84.22

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.28

CX LogP: 1.71

CX LogD: -0.16

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -0.09

References

1. Rodrigues T, da Cruz FP, Lafuente-Monasterio MJ, Gonçalves D, Ressurreição AS, Sitoe AR, Bronze MR, Gut J, Schneider G, Mota MM, Rosenthal PJ, Prudêncio M, Gamo FJ, Lopes F, Moreira R..  (2013)  Quinolin-4(1H)-imines are potent antiplasmodial drugs targeting the liver stage of malaria.,  56  (11): [PMID:23701465] [10.1021/jm400246e]

2.  (2016)  7  (8): [10.1039/C6MD00274A]

3. 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]

4. Deng Y, Wu T, Zhai SQ, Li CH..  (2019)  Recent progress on anti-Toxoplasma drugs discovery: Design, synthesis and screening.,  183  [PMID:31585276] [10.1016/j.ejmech.2019.111711]

5. Guo J, Chen B, Yu Y, Cheng B, Cheng Y, Ju Y, Gu Q, Xu J, Zhou H..  (2020)  Discovery of novel tRNA-amino acid dual-site inhibitors against threonyl-tRNA synthetase by fragment-based target hopping.,  187  [PMID:31821989] [10.1016/j.ejmech.2019.111941]

6. 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]

7. 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]

8. Guo J,Chen B,Yu Y,Cheng B,Ju Y,Tang J,Cai Z,Gu Q,Xu J,Zhou H.  (2020)  Structure-guided optimization and mechanistic study of a class of quinazolinone-threonine hybrids as antibacterial ThrRS inhibitors.,  207  [PMID:32980741] [10.1016/j.ejmech.2020.112848]

9. 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]

10. Cheng B, Cai Z, Luo Z, Luo S, Luo Z, Cheng Y, Yu Y, Guo J, Ju Y, Gu Q, Xu J, Jiang X, Li G, Zhou H..  (2022)  Structure-Guided Design of Halofuginone Derivatives as ATP-Aided Inhibitors Against Bacterial Prolyl-tRNA Synthetase.,  65  (23.0): [PMID:36394909] [10.1021/acs.jmedchem.2c01496]

Source

Source(3):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6