Avicularin - Moligand™, ≥98% , CAS No.572-30-5

CAS: 572-30-5 Cat. No.: A664202 Peso molecular: 434.35 PubChem CID: 5490064

GRADE & PURITY Moligand™, ≥98%

Synonyms

Fenicularin | Quercetin 3-α-L-arabinofuranoside | 3,3 ′, 4 ′, 5,7-pentahydroxyflavone 3-O - α - L furan arabinoside

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Descripción general

Avicularin is an orally active flavonoid. Avicularin inhibits NF-κB (p65), COX-2 and PPAR-γ activities. Avicularin has anti-inflammatory, anti-infectious anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities.

Specifications

Sinónimos

Fenicularin | Quercetin 3-α-L-arabinofuranoside | 3, 3 ′, 4 ′, 5, 7-pentahydroxyflavone 3-O - α - L furan arabinoside

Especificaciones y pureza

Moligand™, ≥98%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C, Protected from light

Enviado en

Wet ice

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

Grado

Moligand™

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(O4)CO)O)O)O)O
• IUPAC Name: 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• InChIKey: BDCDNTVZSILEOY-UXYNSRGZSA-N
• INCHI: 1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1
• Isómeros SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H](O4)CO)O)O)O)O
• PubChem CID: 5490064
• Peso molecular: 434.35

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-3-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides
• Direct Parent: Flavonoid-3-O-glycosides
• Alternative Parents: 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavones Chromones O-glycosyl compounds Pentoses Catechols 1-hydroxy-2-unsubstituted benzenoids Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Heteroaromatic compounds Tetrahydrofurans Vinylogous acids Secondary alcohols Oxacyclic compounds Acetals Hydrocarbon derivatives Primary alcohols Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-3-o-glycoside - 3'-hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Chromone - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Pentose monosaccharide - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Pyranone - Pyran - Monocyclic benzene moiety - Benzenoid - Monosaccharide - Heteroaromatic compound - Vinylogous acid - Tetrahydrofuran - Secondary alcohol - Oxacycle - Acetal - Organoheterocyclic compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Organic oxygen compound - Organic oxide - Primary alcohol - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
• 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

Objetivos asociados (humanos)

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

FASN Tchem Fatty acid synthase (3390 Activities)

Discover Target: FASN

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MCF7 (126967 Activities)

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A549 (127892 Activities)

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Monocyte (474 Activities)

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HeLa (62764 Activities)

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Objetivos asociados (no humanos)

Dolichospermum flos-aquae (8 Activities)

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Aspergillus fumigatus (16427 Activities)

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Candida albicans (78123 Activities)

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Candida parapsilosis (8521 Activities)

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Dengue virus (413 Activities)

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

Discover Target: Trpa1

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

Mecanismos de acción

Propiedades químicas y físicas

• Peso molecular: 434.300 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 434.085 Da
• Monoisotopic Mass: 434.085 Da
• Topological Polar Surface Area: 186.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 711.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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

Referencias

1. Qi Dong, Na Hu, Huilan Yue, Honglun Wang, Yue Wei.  (2022)  Rapid screening of α-glucosidase inhibitors in Hypericum perforatum L. using bio-affinity chromatography coupled with UPLC/MS.  BIOMEDICAL CHROMATOGRAPHY,  37  (2): (e5536).  [PMID:36264709] [10.1002/bmc.5536]

2. You Luo, Haiqing Liu, Shanzhong Yang, Jiarui Zeng, Zhenqiang Wu.  (2019)  Sodium Alginate-Based Green Packaging Films Functionalized by Guava Leaf Extracts and Their Bioactivities.  Materials,  12  (18): (2923).  [PMID:31510022] [10.3390/ma12182923]

3. Zhimin Wang, Fang Li, Yuan Quan, Junye Shen.  (2019)  Avicularin ameliorates human hepatocellular carcinoma via the regulation of NF‑κB/COX‑2/PPAR‑γ activities.  Molecular Medicine Reports,  19  (6): (5417-5423).  [PMID:31059053] [10.3892/mmr.2019.10198]

4. Zhongfei Shen, Yun Xu, Xiaohong Jiang, Zhijian Wang, Yanjun Guo, Weiwei Pan, Jie Hou.  (2019)  Avicularin Relieves Depressive-Like Behaviors Induced by Chronic Unpredictable Mild Stress in Mice.  MEDICAL SCIENCE MONITOR,      [PMID:30986204] [10.12659/MSM.912401]

5. Wei-min Zhang, Rui-fang Li, Ming Sun, Da-ming Hu, Jian-fei Qiu, Yun-hao Yan.  (2014)  UPLC–MS/MS method for determination of avicularin in rat plasma and its application to a pharmacokinetic study.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:25010713] [10.1016/j.jchromb.2014.06.015]

6. Xijin Yang, Ying Li, Qiju Shao, Zhirong Li, Zeli Chun, Yan Wang, Yaping Zhou, Rongxiang Chen.  (2024)  Screening, fingerprinting, and identification of phenolic antioxidants in Persicaria chinensis (L.) H. Gross by liquid chromatography – electrochemical detection and liquid chromatography – tandem mass spectrometry.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:39579741] [10.1016/j.jchromb.2024.124387]