Nepetin - ≥98% , CAS No.520-11-6

CAS: 520-11-6 Cat. No.: N649844 Molecular Weight: 316.27 PubChem CID: 5317284

GRADE & PURITY ≥98%

Synonyms

5,7,3',4'-TETRAHYDROXY-6-METHOXY FLAVONE | EUPAFOLIN | NCGC00163594-01 | REGID_for_CID_5317284 | SR-01000777526-3 | cid_5317284 | DTXSID8061509 | p-hydroxy benzyl alcohol | ?6-METHOXYLUTEOLIN | 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

Storage

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

Shipped In

Ice chest + Ice pads

Overview

Nepetin (6-Methoxyluteolin) is a natural flavonoid isolated from Eupatorium ballotaefolium HBK with potent anti-inflammatory activities. Nepetin inhibits IL-6 , IL-8 and MCP-1 secretion with IC 50 values of 4.43 μM, 3.42 μM and 4.17 μM, respectively in ARPE-19 cells

In Vitro

Pretreatment with Nepetin dose-dependently inhibited IL-6, IL-8 and MCP-1 secretion with IC 50 values of 4.43, 3.42 and 4.17 μM, respectively. Nepetin (2.5-10 μM; 25 hours; ARPE-19 cells) treatment suppresses IL-1β-induced cytokine (IL-6, IL-8 and MCP-1) expression at mRNA level in ARPE-19 cells. Nepetin (2.5-10 μM; 1.5 hours; ARPE-19 cells) treatment dose-dependently inhibits phosphorylation of IKKα/β and IκBα, and nuclear translocation of p65. Nepetin decreases the level of phosphorylated ERK1/2, JNK and p38 MAPK in activated ARPE-19 cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only. RT-PCRCell Line: ARPE-19 cells Concentration: 2.5 μM, 5 μM, 10 μM Incubation Time: 25 hours Result: Suppressed the mRNA expression of IL-6, IL-8 and MCP-1 in ARPE-19 cells. Western Blot AnalysisCell Line: ARPE-19 cells Concentration: 2.5 μM, 5 μM, 10 μM Incubation Time: 1.5 hours Result: Dose-dependently inhibited phosphorylation of IKKα/β and IκBα, and nuclear translocation of p65. Decreased the level of phosphorylated ERK1/2, JNK and p38 MAPK in activated ARPE-19 cells.

Form:Solid

IC50& Target:IL-1 IL-6 IL-8

Specifications

Synonyms

5, 7, 3', 4'-TETRAHYDROXY-6-METHOXY FLAVONE | EUPAFOLIN | NCGC00163594-01 | REGID_for_CID_5317284 | SR-01000777526-3 | cid_5317284 | DTXSID8061509 | p-hydroxy benzyl alcohol | ?6-METHOXYLUTEOLIN | 4H-1-Benzopyran-4-one, 2-(3, 4-dihydroxyphenyl)-5, 7-dihydroxy-

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Nepetin (6-Methoxyluteolin) is a natural flavonoid isolated from Eupatorium ballotaefolium HBK with potent anti-inflammatory activities. Nepetin inhibits IL-6 , IL-8 and MCP-1 secretion with IC 50 values of 4.43 μM, 3.42 μM and 4.17 μM, respectively in AR

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.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
• InChIKey: FHHSEFRSDKWJKJ-UHFFFAOYSA-N
• INCHI: 1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3
• Isomeric SMILES: COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O
• PubChem CID: 5317284
• Molecular Weight: 316.27

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: 6-O-methylated flavonoids
• Alternative Parents: 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-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: 6-methoxyflavonoid-skeleton - 7-hydroxyflavonoid - 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 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 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)

GFER Tchem FAD-linked sulfhydryl oxidase ALR (1 Activities)

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

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

XDH Tclin Xanthine dehydrogenase (1038 Activities)

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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

THRB Tclin Thyroid hormone receptor beta-1 (7926 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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AMY1A Salivary alpha-amylase (100 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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GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)

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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

CASP6 Tchem Caspase-6 (1213 Activities)

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

PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)

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

TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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HepG2 (196354 Activities)

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FEN1 Tchem Flap endonuclease 1 (12055 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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POLH Tchem DNA polymerase eta (21678 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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Liver (3974 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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

RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)

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BLM Tchem Bloom syndrome protein (4248 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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

NPC1 Tchem Niemann-Pick C1 protein (18985 Activities)

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microRNA 21 (64692 Activities)

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GFER Tchem FAD-linked sulfhydryl oxidase ALR (1466 Activities)

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ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

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APOBEC3G Tchem DNA dC->dU-editing enzyme APOBEC-3G (12481 Activities)

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

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HSPA5 Tchem 78 kDa glucose-regulated protein (3319 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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RAPGEF3 Tchem Rap guanine nucleotide exchange factor 3 (15528 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)

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WRN Tbio Werner syndrome ATP-dependent helicase (8824 Activities)

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 integrase (9041 Activities)

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M1AAP Zinc aminopeptidase (902 Activities)

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Plasmodium falciparum (966862 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Hepatitis C virus (23859 Activities)

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Dyrk1a Dual specificity tyrosine-phosphorylation-regulated kinase 1A (1629 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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Cdk5 Cell division protein kinase 5 (15 Activities)

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Nox1 NADPH oxidase 1 (5 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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pos-1 Cytoplasmic zinc-finger protein (1690 Activities)

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mex-5 Zinc finger protein mex-5 (1676 Activities)

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Phosphoglycerate kinase, glycosomal (2184 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 125 mg/mL (395.24 mM; ultrasonic and warming and heat to 60°C)
• Sensitivity: Light sensitive
• Molecular Weight: 316.260 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 316.058 Da
• Monoisotopic Mass: 316.058 Da
• Topological Polar Surface Area: 116.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 491.000
• 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