(±)-Naringenin - Moligand™, analytical standard , CAS No.67604-48-2

CAS: 67604-48-2 Cat. No.: R135669 Fórmula: C₁₅H₁₂O₅ Peso molecular: 272.26 Beilstein Registry Number: 8503 Número EC: 266-769-1

CALIDAD & PUREZA Analytical standard, Moligand™

Synonyms

4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)- | EINECS 266-769-1 | NCGC00017346-04 | NCGC00095963-01 | GTPL10298 | Naringenin (NAR) | FT-0778247 | NSC34875 | NSC-34875 | naringenin

Storage

Store at 2-8°C

Shipped In

Wet ice

Descripción general

(±)-Naringenin is an antioxidant flavonoid. It has anti-inflammatory and antitumor properties. (±)-Naringenin induces apoptosis. It stimulates DNA repair following oxidative damage. (±)-Naringenin inhibits the activity of PI 3-kinase (PI(3)K).
A PI 3-kinase inhibitor.

Application：

(±)-Naringenin, a polyphenolic material, is used to prepare nickel(II) naringenin-oxime complex, which can be used as a catalyst for Mizoroki−Heck cross-coupling reaction.It has been used as a hypochlorite scavenger to prevent the formation of chloramines from oxidation of hypochlorite in the human serum albumin.It induces apoptosis in human pancreatic cancer SNU-213 cells.It also shows cytotoxic effects on various human cancer cells such as breast, cervix, stomach, colon and liver cancer cells.

Especificaciones

Sinónimos

4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)- | EINECS 266-769-1 | NCGC00017346-04 | NCGC00095963-01 | GTPL10298 | Naringenin (NAR) | FT-0778247 | NSC34875 | NSC-34875 | naringenin

Especificaciones y pureza

analytical standard, Moligand™

Mecanismos bioquímicos y fisiológicos

Citrus flavonoid. Antioxidant, anti-inflammatory. Affects various signaling pathways in vitro and in vivo . Crosses the blood-brain barrier.

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™, Patrón analítico

Tipo de acción

AGONIST

Nota

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.

Nombres e identificadores

Pubchem Sid

528753460

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/528753460

Sonrisas canónicas

C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

InChIKey

FTVWIRXFELQLPI-UHFFFAOYSA-N

INCHI

1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2

Isómeros SMILES

C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O

WGK Alemania

3

CAS alternativo

480-41-1,67604-48-2

Número NSC

11855

Términos de entrada MeSH

(2S)-naringenin;4',5,7-trihydroxyflavanone;BE 14348A;BE-14348A;naringenin;naringenin-7-sulfate

Peso molecular

272.26

Beilstein

8503

Reaxy-Rn

280888

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=280888&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Flavonoids
      • Subclass Flavans

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Flavonoids
• Subclass: Flavans
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavanones
• Alternative Parents: 7-hydroxyflavonoids 5-hydroxyflavonoids 4'-hydroxyflavonoids Chromones Aryl alkyl ketones Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Vinylogous acids Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavanone - Hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Chromone - Benzopyran - Chromane - 1-benzopyran - Aryl alkyl ketone - Aryl ketone - 1-hydroxy-4-unsubstituted benzenoid - Phenol - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Ketone - Organoheterocyclic compound - Oxacycle - Ether - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as flavanones. These are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
• External Descriptors: trihydroxyflavanone

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

Objetivos asociados (humanos)

TRPM3 Tchem Transient receptor potential cation channel subfamily M member 3 (1 Activities)

Discover Target: TRPM3

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

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

ACHE Tclin Acetylcholinesterase (18204 Activities)

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

CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 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

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

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

PDK1 Tchem Pyruvate dehydrogenase kinase isoform 1 (2021 Activities)

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

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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MCF7 (126967 Activities)

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HCT-116 (91556 Activities)

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MDA-MB-231 (73002 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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

DGAT1 Tclin Diacylglycerol O-acyltransferase 1 (1719 Activities)

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

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

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GMNN Tbio Geminin (128009 Activities)

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microRNA 21 (64692 Activities)

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CCNE1 Tchem Cyclin-dependent kinase 2/cyclin E1 (1877 Activities)

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

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Objetivos asociados (no humanos)

DPP4 Dipeptidyl peptidase IV (11 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Trypanosoma brucei brucei (13300 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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Luciferin 4-monooxygenase (66902 Activities)

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

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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FTL Ferritin light chain (43324 Activities)

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

ureB Urease subunit alpha/Urease subunit beta (701 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in ethanol (50 mg/ml), DMSO, methanol, and ammonium hydroxide (50 mg/ml). Insoluble in water (almost).
• Punto de ebullición (°C): 577.47 °C
• Punto de fusión (°C): 247-250°C
• Peso molecular: 272.250 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 272.068 Da
• Monoisotopic Mass: 272.068 Da
• Topological Polar Surface Area: 87.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 363.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1