Naringin - Moligand™, analytical standard, ≥98% , Inhibitor of OATP1A2, CAS No.10236-47-2, Inhibitor of OATP1A2

CAS: 10236-47-2 Cat. No.: N107344 Fórmula: C₂₇H₃₂O₁₄ Peso molecular: 580.53 Beilstein Registry Number: 102012 Número EC: 233-566-4

CALIDAD & PUREZA Analytical standard, Moligand™, ≥98%

Synonyms

(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside | (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-betaD-glucopyranos

Storage

Argon charged,Room temperature

Shipped In

Normal

Descripción general

Naringin has been used:
• as a bitter tastant to compare the behavioral response of the Drosophila larva and adult
• to study its anti-inflammatory property and to determine its effect on nucleus pulposus (NP) cells
• to determine its effect on bone metabolism like osteogenic differentiation, inhibition of osteoclast formation

Especificaciones

Sinónimos

(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside | (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-betaD-glucopyranos

Especificaciones y pureza

Moligand™, analytical standard, ≥98%

Mecanismos bioquímicos y fisiológicos

A flavanone glycoside. Neuroprotective. Activates Nrf2. Inhibits expression of pro-inflammatory mediators.

Condiciones de almacenamiento de almacenamiento

Argon charged,Room temperature

Enviado en

Normal

Grado

Analytical standard, Moligand™

Tipo de acción

INHIBITOR

Mecanismo de acción

Inhibitor of OATP1A2

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.

Pureza

≥98%

Nombres e identificadores

Pubchem Sid

508813716

Sonrisas canónicas

CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O

IUPAC Name

(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

InChIKey

DFPMSGMNTNDNHN-ZPHOTFPESA-N

INCHI

1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

Isómeros SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O

WGK Alemania

3

RTECS

QN6340000

Peso molecular

580.53

Beilstein

102012

Reaxy-Rn

25075985

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25075985&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-7-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides
• Direct Parent: Flavonoid-7-O-glycosides
• Alternative Parents: 4'-hydroxyflavonoids 5-hydroxyflavonoids Flavanones Phenolic glycosides Chromones Disaccharides O-glycosyl compounds Aryl alkyl ketones 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Oxanes Benzene and substituted derivatives Vinylogous acids Secondary alcohols Polyols Acetals Oxacyclic compounds Primary alcohols Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-7-o-glycoside - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - Flavanone - Hydroxyflavonoid - Flavan - Phenolic glycoside - Chromone - Disaccharide - Glycosyl compound - O-glycosyl compound - Chromane - Benzopyran - 1-benzopyran - Aryl alkyl ketone - Aryl ketone - Phenol - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - 1-hydroxy-4-unsubstituted benzenoid - Oxane - Benzenoid - Monocyclic benzene moiety - Vinylogous acid - Secondary alcohol - Ketone - Polyol - Acetal - Organoheterocyclic compound - Oxacycle - Ether - Primary alcohol - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Alcohol - Organooxygen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
• External Descriptors: flavanones

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)

SLCO1A2 Tchem Solute carrier organic anion transporter family member 1A2 (0 Activities)

Discover Target: SLCO1A2

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

F2 Tclin Thrombin (11687 Activities)

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CYP19A1 Tclin Cytochrome P450 19A1 (6099 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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FABP4 Tchem Fatty acid binding protein adipocyte (764 Activities)

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

GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

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HPSE Tchem Heparanase (634 Activities)

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

UGT1A4 Tbio UDP-glucuronosyltransferase 1A4 (288 Activities)

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Caco-2 (12174 Activities)

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HepG2 (196354 Activities)

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Monocyte (474 Activities)

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UBE2N Tchem Ubiquitin-conjugating enzyme E2 N (1570 Activities)

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BCL2A1 Tchem Bcl-2-related protein A1 (291 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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

UGT2B15 Tbio UDP-glucuronosyltransferase 2B15 (172 Activities)

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

UGT1A1 Tchem UDP-glucuronosyltransferase 1-1 (448 Activities)

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ERG Tbio Transcriptional regulator ERG (5589 Activities)

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

GMNN Tbio Geminin (128009 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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

SLCO1A2 Tchem Solute carrier organic anion transporter family member 1A2 (104 Activities)

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

SLCO2B1 Tchem Solute carrier organic anion transporter family member 2B1 (580 Activities)

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

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

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

IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

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CYCS Tchem Cytochrome c (68 Activities)

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TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)

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KCNJ3 Tchem Kir3.1/Kir3.4 (583 Activities)

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

KCNJ3 Tchem Kir3.1/Kir3.2 (445 Activities)

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Objetivos asociados (no humanos)

ampC Beta-lactamase AmpC (62480 Activities)

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Abcb1b P-glycoprotein 1 (174 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Salmonella typhimurium (15756 Activities)

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Aggregatibacter actinomycetemcomitans (150 Activities)

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Porphyromonas gingivalis (651 Activities)

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Rattus norvegicus (775804 Activities)

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RAW264.7 (28094 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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BCHE Cholinesterase (8742 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Slco1a5 Solute carrier organic anion transporter family member 1A5 (48 Activities)

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Thoracic aorta (838 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: Moisture sensitive
• Rotación específica [α]: -84 ° (C=2, EtOH)
• Punto de fusión (°C): 166℃
• Peso molecular: 580.500 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 6
• Exact Mass: 580.179 Da
• Monoisotopic Mass: 580.179 Da
• Topological Polar Surface Area: 225.000 Ų
• Heavy Atom Count: 41
• Formal Charge: 0
• Complexity: 884.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• 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