Ebselen - Moligand™, ≥98% , Antioxidant, CAS No.60940-34-3, Antioxidant

CAS: 60940-34-3 Cat. No.: P137293 Molecular Weight: 274.18 EC Number: 612-054-8

GRADE & PURITY Moligand™, ≥98%

Synonyms

Ebselen, cysteine modifier | HMS502P13 | Lopac-E-3520 | Prestwick0_000740 | SCHEMBL33829 | C042986 | NCGC00024072-04 | CID3194 | AC-1124 | BPBio1_000770 | Bio2_000542 | 2-phenyl-1,2-benzoselenazol-3-one | BSPBio_002538 | HMS1791D04 | NCGC00015412-01 | BSP

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Ebselen is an interesting organoselenium compound displaying antiinflammatory and antioxidant properties. Ebselen is shown to inhibit the 5-lipoxygenase (5-LO) and 15-lipoxygenase (15-LO) enzymes in the absence of glutathione. Ebselen also inhibits Cox (cyclooxygenase), PKC (protein kinase C), DECR1 (NADPH), and Mox-1 (NADPH oxidase). The oxidation of low density lipoproteins by free radicals is suppressed by the antioxidant action of Ebselen. Ebselen is an inhibitor of Cox-1, Cox-2, NOS, GST and IDO.
An inhibitor of 5-LO, 15-LO, Cox, NADPH, and NADPH oxidase.

application：

Ebselen has been used as a:voltage-dependent calcium channels (VDCCs) blocker；glutathione peroxidase mimetic to test its inhibitory effect on contraction-mediated deoxy glucose (2-DG) uptake in mouse；extensor digitorum longus (fast-twitch) muscle

glucocerebrosidase inhibitor；hepatitis C virus helicase inhibitor

Specifications

Synonyms

Ebselen, cysteine modifier | HMS502P13 | Lopac-E-3520 | Prestwick0_000740 | SCHEMBL33829 | C042986 | NCGC00024072-04 | CID3194 | AC-1124 | BPBio1_000770 | Bio2_000542 | 2-phenyl-1, 2-benzoselenazol-3-one | BSPBio_002538 | HMS1791D04 | NCGC00015412-01 | BSP

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

An organo-selenium compound possessing antioxidant properties. Inhibits mammalian lipoxygenases in the absence of thiol groups, and glutathione S-transferase and papain via the interaction with cysteine residues. Also inhibits indoleamine 2, 3-dioxygenase

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Mechanism of action

Antioxidant

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504750646
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750646
• Canonical Smiles: C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C3[Se]2
• IUPAC Name: 2-phenyl-1,2-benzoselenazol-3-one
• InChIKey: DYEFUKCXAQOFHX-UHFFFAOYSA-N
• INCHI: 1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H
• Isomeric SMILES: C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C3[Se]2
• WGK Germany: 3
• Molecular Weight: 274.18
• Reaxy-Rn: 164926
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=164926&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Selenazoles Heteroaromatic compounds Lactams Azacyclic compounds Organoselenium compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Monocyclic benzene moiety - Heteroaromatic compound - 1,2-selenazole - Lactam - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organoselenium compound - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
• External Descriptors: benzoselenazole

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

EHMT2 Tchem Histone-lysine N-methyltransferase EHMT2 (1 Activities)

Discover Target: EHMT2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

EHMT1 Tchem Histone-lysine N-methyltransferase EHMT1 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

IDE Tchem Insulin-degrading enzyme (2 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

EPHX2 Tchem Bifunctional epoxide hydrolase 2 (3 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GALE Tchem UDP-glucose 4-epimerase (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PMM2 Tchem Phosphomannomutase 2 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PHOSPHO1 Tchem Phosphoethanolamine/phosphocholine phosphatase (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MPI Tchem Mannose-6-phosphate isomerase (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MIF Tchem Macrophage migration inhibitory factor (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

BBOX1 Tchem Gamma-butyrobetaine dioxygenase (5 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

IDO1 Tchem Indoleamine 2,3-dioxygenase 1 (2 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

INSR Tclin Insulin receptor (5558 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

VDR Tclin Vitamin D receptor (26531 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDGFRB Tclin Platelet-derived growth factor receptor beta (5195 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

IGF1R Tclin Insulin-like growth factor I receptor (8605 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ANPEP Tchem Aminopeptidase N (863 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MIF Tchem Macrophage migration inhibitory factor (979 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

POLB Tchem DNA polymerase beta (23632 Activities)

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TRPV1 Tclin Vanilloid receptor (8273 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FGFR1 Tclin Fibroblast growth factor receptor 1 (9149 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDOA Tbio Fructose-bisphosphate aldolase A (1 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SRC Tclin Tyrosine-protein kinase SRC (10310 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BCHE Tclin Butyrylcholinesterase (7174 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APP Tclin Amyloid-beta A4 protein (8510 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GLA Tclin Alpha-galactosidase A (5444 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALB Tchem Serum albumin (2651 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

METAP2 Tchem Methionine aminopeptidase 2 (1512 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AURKB Tchem Serine/threonine-protein kinase Aurora-B (6805 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RPS6KA4 Tchem Ribosomal protein S6 kinase alpha 4 (2104 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PIM1 Tchem Serine/threonine-protein kinase PIM1 (9629 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SYK Tclin Tyrosine-protein kinase SYK (7372 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX12 Tchem Arachidonate 12-lipoxygenase (3262 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HDAC3 Tclin Histone deacetylase 3 (3654 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTK2 Tclin Focal adhesion kinase 1 (4730 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HK1 Tchem Hexokinase type I (266 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MET Tclin Hepatocyte growth factor receptor (10718 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PRKCA Tchem Protein kinase C alpha (5923 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EPHX2 Tchem Epoxide hydratase (3844 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FYN Tclin Tyrosine-protein kinase FYN (5308 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HDAC9 Tclin Histone deacetylase 9 (708 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LYN Tclin Tyrosine-protein kinase Lyn (4251 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MPI Tchem Mannose-6-phosphate isomerase (940 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

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Cruzipain (33337 Activities)

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polC DNA polymerase III (243 Activities)

Discover Target: polC

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac5 Histone deacetylase 5 (5 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Streptococcus (3973 Activities)

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Enterococcus (1748 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Enterobacter cloacae (7976 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Acinetobacter baumannii (41033 Activities)

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Citrobacter freundii (1864 Activities)

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Escherichia coli (133304 Activities)

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Klebsiella oxytoca (929 Activities)

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Morganella morganii (1291 Activities)

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Enterococcus faecium (13803 Activities)

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Listeria monocytogenes (2626 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Enterococcus faecalis (29875 Activities)

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Mycolicibacterium smegmatis (8003 Activities)

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Trypanosoma brucei (78846 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Bos taurus (956 Activities)

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Gerbillinae (442 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Salmonella enterica (1497 Activities)

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Streptococcus sp. 'group A' (3417 Activities)

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CHO (4503 Activities)

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CHO-K1 (1115 Activities)

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PC-12 (7051 Activities)

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HT-22 (3261 Activities)

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Murine-murine hybridoma (mark 3) (19 Activities)

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Luciferase (58 Activities)

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TRXR Thioredoxin reductase (20 Activities)

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lef Anthrax lethal factor (7585 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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Npsr1 Neuropeptide S receptor (260 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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PYK Pyruvate kinase (6726 Activities)

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botA Botulinum neurotoxin type A (1303 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility in water: insoluble Solubility in other solvents: soluble in methanol, ethanol, THF, ethyl acetate, DMSO
• Sensitivity: heat sensitive；Air sensitive
• Melt Point(°C): 183 °C
• Molecular Weight: 274.190 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 274.985 Da
• Monoisotopic Mass: 274.985 Da
• Topological Polar Surface Area: 20.300 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 275.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

References

1. Minglu Li, Hui Han, Shengmei Song, Shaomin Shuang, Chuan Dong.  (2021)  AIE-based fluorescent boronate probe and its application in peroxynitrite imaging.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:34118522] [10.1016/j.saa.2021.120044]

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