ISATORIBINE

ID: ALA2105116

Max Phase: Phase

Molecular Formula: C10H12N4O6S

Molecular Weight: 316.30

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  Nc1nc(=O)c2sc(=O)n([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2[nH]1

Standard InChI:  InChI=1S/C10H12N4O6S/c11-9-12-6-5(7(18)13-9)21-10(19)14(6)8-4(17)3(16)2(1-15)20-8/h2-4,8,15-17H,1H2,(H3,11,12,13,18)/t2-,3-,4-,8-/m1/s1

Standard InChI Key:  TZYVRXZQAWPIAB-FCLHUMLKSA-N

Associated Targets(Human)

Histone deacetylase 6 20808 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rattus norvegicus 775804 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mus musculus 284745 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

YAC-1 251 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Semliki Forest virus 705 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

SARS-CoV-2 38078 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Replicase polyprotein 1ab 11336 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Properties

Molecular Weight: 316.30Molecular Weight (Monoisotopic): 316.0478AlogP: -2.66#Rotatable Bonds: 2
Polar Surface Area: 163.69Molecular Species: NEUTRALHBA: 10HBD: 5
#RO5 Violations: 0HBA (Lipinski): 10HBD (Lipinski): 6#RO5 Violations (Lipinski): 1
CX Acidic pKa: 11.81CX Basic pKa: 3.15CX LogP: -2.56CX LogD: -2.56
Aromatic Rings: 2Heavy Atoms: 21QED Weighted: 0.40Np Likeness Score: 0.70

References

1. Bontems RJ, Anderson JD, Smee DF, Jin A, Alaghamandan HA, Sharma BS, Jolley WB, Robins RK, Cottam HB..  (1990)  Guanosine analogues. Synthesis of nucleosides of certain 3-substituted 6-aminopyrazolo[3,4-d]pyrimidin-4(5H)-ones as potential immunotherapeutic agents.,  33  (8): [PMID:2165164] [10.1021/jm00170a020]
2. Girgis NS, Michael MA, Smee DF, Alaghamandan HA, Robins RK, Cottam HB..  (1990)  Direct C-glycosylation of guanine analogues: the synthesis and antiviral activity of certain 7- and 9-deazaguanine C-nucleosides.,  33  (10): [PMID:2170645] [10.1021/jm00172a011]
3. Kini GD, Anderson JD, Sanghvi YS, Lewis AF, Smee DF, Revankar GR, Robins RK, Cottam HB..  (1991)  Synthesis and antiviral activity of certain guanosine analogues in the thiazolo[4,5-d]pyrimidine ring system.,  34  (10): [PMID:1656042] [10.1021/jm00114a008]
4. Nagahara K, Anderson JD, Kini GD, Dalley NK, Larson SB, Smee DF, Jin A, Sharma BS, Jolley WB, Robins RK..  (1990)  Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.,  33  (1): [PMID:2153211] [10.1021/jm00163a064]
5. Bonnet PA, Robins RK..  (1993)  Modulation of leukocyte genetic expression by novel purine nucleoside analogues. A new approach to antitumor and antiviral agents.,  36  (6): [PMID:8459394] [10.1021/jm00058a001]
6. Kuppast B, Fahmy H..  (2016)  Thiazolo[4,5-d]pyrimidines as a privileged scaffold in drug discovery.,  113  [PMID:26942627] [10.1016/j.ejmech.2016.02.031]
7. Cherukupalli S, Hampannavar GA, Chinnam S, Chandrasekaran B, Sayyad N, Kayamba F, Reddy Aleti R, Karpoormath R..  (2018)  An appraisal on synthetic and pharmaceutical perspectives of pyrazolo[4,3-d]pyrimidine scaffold.,  26  (2): [PMID:29273417] [10.1016/j.bmc.2017.10.012]
8. 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]
9. 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]
10. 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]
11. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]
12. 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]