ID: ALA216543

Max Phase: Preclinical

Molecular Formula: C16H11N3O2

Molecular Weight: 277.28

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C1Nc2ccccc2/C1=C1/Nc2ccccc2/C1=N\O

Standard InChI:  InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17,21H,(H,18,20)/b15-13-,19-14+

Standard InChI Key:  HBDSHCUSXQATPO-BGBJRWHRSA-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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 277.28

Molecular Weight (Monoisotopic): 277.0851

AlogP: 2.65

#Rotatable Bonds: 0

Polar Surface Area: 73.72

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.36

CX Basic pKa: 1.51

CX LogP: 1.79

CX LogD: 1.48

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.39

Np Likeness Score: 0.27

References

1. PubChem BioAssay data set, 

2. PubChem BioAssay data set, 

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8. Wagman AS, Boyce RS, Brown SP, Fang E, Goff D, Jansen JM, Le VP, Levine BH, Ng SC, Ni ZJ, Nuss JM, Pfister KB, Ramurthy S, Renhowe PA, Ring DB, Shu W, Subramanian S, Zhou XA, Shafer CM, Harrison SD, Johnson KW, Bussiere DE..  (2017)  Synthesis, Binding Mode, and Antihyperglycemic Activity of Potent and Selective (5-Imidazol-2-yl-4-phenylpyrimidin-2-yl)[2-(2-pyridylamino)ethyl]amine Inhibitors of Glycogen Synthase Kinase 3.,  60  (20): [PMID:29016121] [10.1021/acs.jmedchem.7b00922]

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12. 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]

13. 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]

14. 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]

15. Anh DT,Hai PT,Dung DTM,Dung PTP,Huong LT,Park EJ,Jun HW,Kang JS,Kwon JH,Tung TT,Han SB,Nam NH.  (2020)  Design, synthesis and evaluation of novel indirubin-based N-hydroxybenzamides, N-hydroxypropenamides and N-hydroxyheptanamides as histone deacetylase inhibitors and antitumor agents.,  30  (22): [PMID:32916298] [10.1016/j.bmcl.2020.127537]

16. 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]

17. Cao Z, Yang F, Wang J, Gu Z, Lin S, Wang P, An J, Liu T, Li Y, Li Y, Lin H, Zhao Y, He B..  (2021)  Indirubin Derivatives as Dual Inhibitors Targeting Cyclin-Dependent Kinase and Histone Deacetylase for Treating Cancer.,  64  (20.0): [PMID:34624191] [10.1021/acs.jmedchem.1c01311]

18. Wang H, Wang Z, Wei C, Wang J, Xu Y, Bai G, Yao Q, Zhang L, Chen Y..  (2021)  Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship.,  223  [PMID:34161865] [10.1016/j.ejmech.2021.113652]

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20. Li H, Mattingly AE, Smith RD, Melander RJ, Ernst RK, Melander C..  (2023)  6-Bromoindirubin-3'-oxime derivatives are highly active colistin adjuvants against Klebsiella pneumoniae.,  14  (2.0): [PMID:36846374] [10.1039/d2md00370h]

Source

Source(4):

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