Rose Bengal

ID: ALA2359093

Chembl Id: CHEMBL2359093

Cas Number: 11121-48-5

PubChem CID: 32343

Max Phase: Approved

Molecular Formula: C20H2Cl4I4Na2O5

Molecular Weight: 973.67

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Acid red 94 | Aka105(1) | Bengal rose b sodium salt | Japan red 105-1 | Red no. 105-1 | Rose bengal disodium | Rose bengal disodium salt | Rose bengal extra | Rose bengal sodium salt | Rose bengal sodium|Acid Red 94|Bengal Rose B sodium salt|Rose bengal extra|Rose Bengal disodium|Japan red 105-1|Red no. 105-1|PV-10 sodium|Aka105(1)|11121-48-5|632-69-9 (sodium)|DTXCID702814|DTXSID4022814|956575SN5L|SODIUM TETRAIODOTETRACHLOROFLUORESCEIN|Rose Bengal, 90%, indicator|ROSE BENGAL SODIUM (MART.)|ROSE Show More

Canonical SMILES:  O=C([O-])c1c(Cl)c(Cl)c(Cl)c(Cl)c1-c1c2cc(I)c(=O)c(I)c-2oc2c(I)c([O-])c(I)cc12.[Na+].[Na+]

Standard InChI:  InChI=1S/C20H4Cl4I4O5.2Na/c21-10-8(9(20(31)32)11(22)13(24)12(10)23)7-3-1-5(25)16(29)14(27)18(3)33-19-4(7)2-6(26)17(30)15(19)28;;/h1-2,29H,(H,31,32);;/q;2*+1/p-2

Standard InChI Key:  UWBXIFCTIZXXLS-UHFFFAOYSA-L

Associated Targets(Human)

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB11 Tchem Bile salt export pump (2311 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PANC-1 (6144 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Slc18a3 Vesicular acetylcholine transporter (102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slco1a1 Solute carrier organic anion transporter family member 1A1 (265 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHO (4503 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
secA1 Protein translocase subunit SecA 1 (13 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
secA2 Protein translocase subunit SecA 2 (3 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
B16-F10 (4610 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
B16-F10-luc2 (37 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
unidentified influenza virus (265 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Human immunodeficiency virus (3636 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vesicular stomatitis virus (4460 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: 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

Calculated Properties

Molecular Weight: 973.67Molecular Weight (Monoisotopic): 971.4992AlogP: 9.00#Rotatable Bonds: 2
Polar Surface Area: 87.74Molecular Species: ACIDHBA: 4HBD: 2
#RO5 Violations: 2HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski): 2
CX Acidic pKa: 2.55CX Basic pKa: 1.89CX LogP: 8.78CX LogD: 3.69
Aromatic Rings: 2Heavy Atoms: 33QED Weighted: 0.09Np Likeness Score: 0.29

References

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5. PubChem BioAssay data set, 
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7. McEwan C, Nesbitt H, Nicholas D, Kavanagh ON, McKenna K, Loan P, Jack IG, McHale AP, Callan JF..  (2016)  Comparing the efficacy of photodynamic and sonodynamic therapy in non-melanoma and melanoma skin cancer.,  24  (13): [PMID:27234890] [10.1016/j.bmc.2016.05.015]
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10. Chen HJ, Zhou XB, Wang AL, Zheng BY, Yeh CK, Huang JD..  (2018)  Synthesis and biological characterization of novel rose bengal derivatives with improved amphiphilicity for sono-photodynamic therapy.,  145  [PMID:29324346] [10.1016/j.ejmech.2017.12.091]
11. 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]
12. Dhillon SK, Porter SL, Rizk N, Sheng Y, McKaig T, Burnett K, White B, Nesbitt H, Matin RN, McHale AP, Callan B, Callan JF..  (2020)  Rose Bengal-Amphiphilic Peptide Conjugate for Enhanced Photodynamic Therapy of Malignant Melanoma.,  63  (3): [PMID:31940202] [10.1021/acs.jmedchem.9b01802]
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. International Nonproprietary Names for Pharmaceutical Substances (INN), 
16. Maia M, Resende DISP, Durães F, Pinto MMM, Sousa E..  (2021)  Xanthenes in Medicinal Chemistry - Synthetic strategies and biological activities.,  210  [PMID:33310284] [10.1016/j.ejmech.2020.113085]
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