Ginsenoside Rg5 - Moligand™,≥99% , CAS No.186763-78-0

CAS: 186763-78-0 Cat. No.: G649467 Molecular Weight: 767.00 EC Number: 109-889-0

GRADE & PURITY Moligand™, ≥99%

Synonyms

(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2E)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Ginsenoside Rg5 is the main component of Red ginseng and IGF-1R agonist. Ginsenoside Rg5 compets for the binding site of IGF-1R and blocks the binding of IGF-1 to IGF-1R (IC50 about 90 nM). Ginsenoside Rg5 also inhibits the mRNA expression of COX-2 via suppression of the DNA binding activities of NF-κB p65.

Specifications

Synonyms

(2S, 3R, 4S, 5S, 6R)-2-[(2R, 3R, 4S, 5S, 6R)-4, 5-dihydroxy-6-(hydroxymethyl)-2-[[(3S, 5R, 8R, 9R, 10R, 12R, 13R, 14R, 17S)-12-hydroxy-4, 4, 8, 10, 14-pentamethyl-17-[(2E)-6-methylhepta-2, 5-dien-2-yl]-2, 3, 5, 6, 7, 9, 11, 12, 13, 15, 16, 17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Ginsenoside Rg5 is the main component of Red ginseng. Ginsenoside blocks binding of IGF-1 to its receptor with an IC 50 of ~90 nM. Ginsenoside Rg5 also inhibits the mRNA expression of COX-2 via suppression of the DNA binding activities of NF-κB p65 .

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

Moligand™

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC(=CCC=C(C)C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)C)C
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2E)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• InChIKey: NJUXRKMKOFXMRX-RNCAKNGISA-N
• INCHI: 1S/C42H70O12/c1-21(2)10-9-11-22(3)23-12-16-42(8)30(23)24(45)18-28-40(6)15-14-29(39(4,5)27(40)13-17-41(28,42)7)53-38-36(34(49)32(47)26(20-44)52-38)54-37-35(50)33(48)31(46)25(19-43)51-37/h10-11,23-38,43-50H,9,12-20H2,1-8H3/b22-11+/t23-,24-,25-,26-,27+,28-,29+,30+,31-,32-,33+,34+,35-,36-,37+,38+,40+,41-,42-/m1/s1
• Isomeric SMILES: CC(=CC/C=C(\C)/[C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)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)C)O)C)C
• Molecular Weight: 767.00

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 Steroidal glycosides 14-alpha-methylsteroids 12-hydroxysteroids O-glycosyl compounds Disaccharides Oxanes Secondary alcohols Cyclic alcohols and derivatives Polyols Oxacyclic compounds Acetals Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Triterpene saponin - Triterpenoid - Steroidal glycoside - 12-hydroxysteroid - 14-alpha-methylsteroid - Hydroxysteroid - Steroid - Disaccharide - Glycosyl compound - O-glycosyl compound - Oxane - Cyclic alcohol - Secondary alcohol - Polyol - Acetal - Oxacycle - Organoheterocyclic compound - Primary alcohol - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - 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: triterpenoid saponin

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

HCT-8 (3484 Activities)

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

A549 (127892 Activities)

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KB (17409 Activities)

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

SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)

Discover Target: SIRT1

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 50 mg/mL (65.19 mM; Need ultrasonic)
• Molecular Weight: 767.000 g/mol
• XLogP3: 5.400
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 9
• Exact Mass: 766.487 Da
• Monoisotopic Mass: 766.487 Da
• Topological Polar Surface Area: 199.000 Ų
• Heavy Atom Count: 54
• Formal Charge: 0
• Complexity: 1380.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 19
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. 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]