Naringin - Moligand™, ≥90%, from citrus fruit , CAS No.10236-47-2

CAS: 10236-47-2 Cat. No.: N431264 분자식: C₂₇H₃₂O₁₄ 분자량: 580.53 Beilstein Registry Number: 102012 EC 번호: 233-566-4

GRADE & PURITY Moligand™, ≥90%, from citrus fruit

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

Room temperature

개요

Naringin is a flavanone glycoside.

Application

Naringin has been used in a study to assess aldosterone production by a human adrenocortical cell line. Long-term naringin consumption reverses a glucose uptake defect and can be used to improve cognitive deficits of Alzheimer′s disease.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N1376.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit .com/metlin.

Specifications

동의어

(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

사양 및 순도

Moligand™, ≥90%, from citrus fruit

생화학 및 생리적 메커니즘

Naringin, a flavanoid in grapefruit and other citrus fruits, potently inhibits intestinal organic anion-transporting polypeptide 1A2 (OATP1A2). Grapefruit juice thereby reduces bioavailability of many pharmacological agents taken at the same time.

보관 조건

Room temperature

등급

Moligand™

순수함

≥90%

이름과 식별자

정식 스마일

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

이성체 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 독일

3

RTECS

QN6340000

분자량

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
    • 분류 Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-7-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• 분류: 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
• 설명: 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

관련 대상(인간)

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

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

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HPSE Tchem Heparanase (634 Activities)

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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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UGT2B15 Tbio UDP-glucuronosyltransferase 2B15 (172 Activities)

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

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ERG Tbio Transcriptional regulator ERG (5589 Activities)

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

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

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

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

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관련 대상(비인간)

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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작용 메커니즘

화학 및 물리적 특성

• 특정 회전[α]: -84 ° (C=2, EtOH)
• 녹는점(°C): 166℃
• 분자량: 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