Cirsiliol - Moligand™,≥98% , CAS No.34334-69-5

CAS: 34334-69-5 Cat. No.: C651477 Molecular Weight: 330.29 EC Number: 809-104-8 PubChem CID: 160237

GRADE & PURITY Moligand™, ≥98%

Synonyms

3',4',5-Trihydroxy-6,7-dimethoxyflavone | 3',4',5-trihydroxy-6,7-dimethoxy-flavone | PbS Quantum Dots-1600 nm | 5,3'',4''-Trihydroxy-6,7-dimethoxyflavone | 5,3',4'-trihydroxy-6,7-dimethoxyflavone | LMPK12111227 | E80755 | 2-(3,4-Dihydroxy-phenyl)-5-hydrox

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Cirsiliol is a potent and selective 5-lipoxygenase inhibitor and a competitive low affinity benzodiazepine receptor ligand.

In Vitro（for reference only）

In concentrations from 0.01 to 300 μM, cirsiliol causes concentration-dependent relaxation of rat isolated ileum. Cirsiliol may inhibit Ca 2+ influx but stimulates Ca 2+ release from intracellular stores. Treatment with rhamnetin or cirsiliol reduces the proliferation of NSCLC cells through the suppression of radiation-induced Notch-1 expression. 

In Vivo（for reference only）

In xenograft mouse model, tumor volume is significantly reduced by combinational treatment with irradiation and rhamnetin or cirsiliol compared with irradiation alone.

Cell Assay

NSCLC, NCI-H1299, NCI-H460, WI-26 VA4 and MRC-5 cell lines are exposed to a single dose of γ-rays. Cells are then treated with rhamnetin and cirsiliol (5, 10, 15, 20, 25 μM) dissolved in DMSO for 4 h.

Form:Solid

IC50& Target:5-Lipoxygenase

Specifications

Synonyms

3', 4', 5-Trihydroxy-6, 7-dimethoxyflavone | 3', 4', 5-trihydroxy-6, 7-dimethoxy-flavone | PbS Quantum Dots-1600 nm | 5, 3'', 4''-Trihydroxy-6, 7-dimethoxyflavone | 5, 3', 4'-trihydroxy-6, 7-dimethoxyflavone | LMPK12111227 | E80755 | 2-(3, 4-Dihydroxy-phenyl)-5-hydrox

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Cirsiliol is a potent and selective 5-lipoxygenase inhibitor and a competitive low affinity benzodiazepine receptor ligand.

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O)OC
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one
• InChIKey: IMEYGBIXGJLUIS-UHFFFAOYSA-N
• INCHI: 1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3
• Isomeric SMILES: COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O)OC
• WGK Germany: 3
• RTECS: DJ3011100
• PubChem CID: 160237
• Molecular Weight: 330.29

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass O-methylated flavonoids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: O-methylated flavonoids
• Intermediate Tree Nodes: Not available
• Direct Parent: 7-O-methylated flavonoids
• Alternative Parents: 6-O-methylated flavonoids 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids Flavones Chromones Anisoles Catechols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Pyranones and derivatives Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 7-methoxyflavonoid-skeleton - 6-methoxyflavonoid-skeleton - 3'-hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Chromone - Benzopyran - 1-benzopyran - Anisole - Catechol - Alkyl aryl ether - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Pyranone - Benzenoid - Pyran - Monocyclic benzene moiety - Vinylogous acid - Heteroaromatic compound - Ether - Organoheterocyclic compound - Oxacycle - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
• External Descriptors: Flavones and Flavonols

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)

ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

Discover Target: ALOX5

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

XDH Tclin Xanthine dehydrogenase (1038 Activities)

Discover Target: XDH

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

AKR1B1 Tclin Aldose reductase (1404 Activities)

Discover Target: AKR1B1

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

CYP1B1 Tchem Cytochrome P450 1B1 (1148 Activities)

Discover Target: CYP1B1

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

JAK2 Tclin Tyrosine-protein kinase JAK2 (12915 Activities)

Discover Target: JAK2

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

CYP1A1 Tchem Cytochrome P450 1A1 (1169 Activities)

Discover Target: CYP1A1

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

STAT3 Tchem Signal transducer and activator of transcription 3 (3313 Activities)

Discover Target: STAT3

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MCF7 (126967 Activities)

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MDA-MB-468 (9477 Activities)

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OVCAR-3 (48710 Activities)

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HCT-116 (91556 Activities)

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IGROV-1 (47897 Activities)

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IL6ST Tclin Interleukin-6 receptor subunit beta (58 Activities)

Discover Target: IL6ST

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Associated Targets(non-human)

Staphylococcus aureus (210822 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : ≥ 25 mg/mL (75.69 mM)
• Sensitivity: light sensitive
• Molecular Weight: 330.290 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 330.074 Da
• Monoisotopic Mass: 330.074 Da
• Topological Polar Surface Area: 105.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 505.000
• 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