Ginsenoside Rf - analytical standard, ≥98% , CAS No.52286-58-5

CAS: 52286-58-5 Cat. No.: G107711 Molecular Weight: 801.01 EC Number: 634-870-3 PubChem CID: 441922

GRADE & PURITY Analytical standard, ≥98%

Synonyms

.BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,6.ALPHA.,12.BETA.)-3,12,20-TRIHYDROXYDAMMAR-24-EN-6-YL 2-O-.BETA.-D-GLUCOPYRANOSYL- | UNII-JOS8BON5YW | (beta,6alpha,12beta)-3,12,20-trihydroxydammar-24-en-6-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside | HY-N0601

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Ginsenoside Rf, a glycoside of protopanaxatriol from Panax ginseng, is shown to be a biologically active saponin found to regulate lipoprotein metabolism. Mechanistic studies report that this regulation is done via altering of peroxisome proliferator-activated receptor α (PPARα)-mediated pathways. PPARα has demonstrated the ability to regulate C-III mRNA and basal levels of hepatic apoA-I (apolipoprotein A-I) which affect lipoprotein metabolism. Additional experiments have also observed this Ginsenoside Rf's ability to inhibit Ca2+ channels in mammalian sensory neurons in vitro.
A glycoside found to mediate lipoprotein metabolism

Specifications

Synonyms

.BETA.-D-GLUCOPYRANOSIDE, (3.BETA., 6.ALPHA., 12.BETA.)-3, 12, 20-TRIHYDROXYDAMMAR-24-EN-6-YL 2-O-.BETA.-D-GLUCOPYRANOSYL- | UNII-JOS8BON5YW | (beta, 6alpha, 12beta)-3, 12, 20-trihydroxydammar-24-en-6-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside | HY-N0601

Specifications & Purity

analytical standard, ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard

Purity

≥98%

Names and Identifiers

• Canonical Smiles: [H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@@]2([H])O[C@H]3C[C@]4(C)[C@]([H])(C[C@@H](O)[C@]5([H])[C@]([H])(CC[C@@]45C)[C@@](C)(O)CC\C=C(/C)C)[C@@]6(C)CC[C@H](O)C(C)(C)[C@]36[H]
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• InChIKey: UZIOUZHBUYLDHW-XUBRWZAZSA-N
• INCHI: 1S/C42H72O14/c1-20(2)10-9-13-42(8,52)21-11-15-40(6)28(21)22(45)16-26-39(5)14-12-27(46)38(3,4)35(39)23(17-41(26,40)7)53-37-34(32(50)30(48)25(19-44)55-37)56-36-33(51)31(49)29(47)24(18-43)54-36/h10,21-37,43-52H,9,11-19H2,1-8H3/t21-,22+,23-,24+,25+,26+,27-,28-,29+,30+,31-,32-,33+,34+,35-,36-,37+,39+,40+,41+,42-/m0/s1
• Isomeric SMILES: CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(C[C@@H]([C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)C)O)C
• WGK Germany: 3
• RTECS: LY9536900
• PubChem CID: 441922
• Molecular Weight: 801.01

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene glycosides
        • Level5 Triterpene glycosides
          • Level6 Triterpene saponins

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Triterpene glycosides
• Direct Parent: Triterpene saponins
• Alternative Parents: Triterpenoids 3-beta-hydroxysteroids 14-alpha-methylsteroids 12-hydroxysteroids O-glycosyl compounds Disaccharides Oxanes Tertiary alcohols Secondary alcohols Cyclic alcohols and derivatives Polyols Oxacyclic compounds Acetals Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Triterpene saponin - Triterpenoid - 20-hydroxysteroid - 3-hydroxysteroid - 14-alpha-methylsteroid - 12-hydroxysteroid - Hydroxysteroid - 3-beta-hydroxysteroid - Steroid - Disaccharide - Glycosyl compound - O-glycosyl compound - Oxane - Cyclic alcohol - Tertiary alcohol - Secondary alcohol - Polyol - Organoheterocyclic compound - Oxacycle - Acetal - Organooxygen compound - Alcohol - Hydrocarbon derivative - Organic oxygen compound - Primary alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
• External Descriptors: Dammarenes

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)

DU-145 (51482 Activities)

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HCT-8 (3484 Activities)

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A549 (127892 Activities)

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KB (17409 Activities)

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Associated Targets(non-human)

Mus musculus (284745 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 801.000 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 10
• Exact Mass: 800.492 Da
• Monoisotopic Mass: 800.492 Da
• Topological Polar Surface Area: 239.000 Ų
• Heavy Atom Count: 56
• Formal Charge: 0
• Complexity: 1410.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 21
• 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

References

1. Ren Rongfan, Li Hongli, Jiang Qing, Wang Xing, Chen David Da Yong.  (2022)  Characterization of ginsenoside structural isomers from mixtures using in situ methylation with direct analysis in real-time ionization tandem mass spectrometry.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,  415  (5): (887-897).  [PMID:36571591] [10.1007/s00216-022-04482-w]

2. Nan Zhao, Mengchun Cheng, Shuai Huang, Dan Liu, Qiang Zhao, Yunpeng Bai, Xiaozhe Zhang.  (2019)  Various Multicharged Anions of Ginsenosides in Negative Electrospray Ionization with QTOF High-Resolution Mass Spectrometry.  JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY,      [PMID:30644055] [10.1007/s13361-018-2089-5]

3. Jiahong Han, Min Dai, Yan Zhao, Enbo Cai, Lianxue Zhang, Xiaohuan Jia, Nian Sun, Xuan Fei, Hui Shu.  (2019)  Compatibility effects of ginseng and Ligustrum lucidum Ait herb pair on hematopoietic recovery in mice with cyclophosphamide-induced myelosuppression and its material basis.  Journal of Ginseng Research,      [PMID:32148411] [10.1016/j.jgr.2019.01.001]

4. Jiawei Yang, Pengcheng Xu, Haoming Li, Haichun Gao, Shaoan Cheng, Chaofeng Shen.  (2024)  Enhancing Extracellular Electron Transfer of a 3D-Printed Shewanella Bioanode with Riboflavin-Modified Carbon Black Bioink.  ACS Applied Bio Materials,      [PMID:38651321] [10.1021/acsabm.3c01088]