Rhapontigenin 3'-O-glucoside - Moligand™, ≥99% , CAS No.94356-22-6

CAS: 94356-22-6 Cat. No.: R650547 Molecular Weight: 420.41 PubChem CID: 45033634

GRADE & PURITY Moligand™, ≥99%

Synonyms

(2S,3R,4S,5S,6R)-2-(5-((E)-3,5-Dihydroxystyryl)-2-methoxyphenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

In Vitro

Rhapontigenin exhibits a potent and selective inhibition of human P450 1A1 with an IC 50 of 0.4 μM. Rhapontigenin shows 400-fold selectivity for P450 1A1 over P450 1A2 and 23-fold selectivity for P450 1A1 over P450 1B1. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

Specifications

Synonyms

(2S, 3R, 4S, 5S, 6R)-2-(5-((E)-3, 5-Dihydroxystyryl)-2-methoxyphenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3, 4, 5-triol

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Rhapontigenin 3'-O-glucoside is a derivative of Rhapontigenin. Rhapontigenin is a potent inactivator of human P450 1A1 and is a good candidate for a cancer chemopreventive agent.

Storage

Protected from light, 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™

Purity

≥99%

Names and Identifiers

• Canonical Smiles: COC1=C(C=C(C=C1)C=CC2=CC(=CC(=C2)O)O)OC3C(C(C(C(O3)CO)O)O)O
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• InChIKey: NMZBFHDKUAVGLR-DXKBKAGUSA-N
• INCHI: 1S/C21H24O9/c1-28-15-5-4-11(2-3-12-6-13(23)9-14(24)7-12)8-16(15)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C/C2=CC(=CC(=C2)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• PubChem CID: 45033634
• Molecular Weight: 420.41

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Stilbenes
      • Subclass Stilbene glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Stilbenes
• Subclass: Stilbene glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Stilbene glycosides
• Alternative Parents: Phenolic glycosides Hexoses O-glycosyl compounds Styrenes Resorcinols Phenoxy compounds Methoxybenzenes Anisoles 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Oxanes Secondary alcohols Polyols Acetals Oxacyclic compounds Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Stilbene glycoside - Phenolic glycoside - Hexose monosaccharide - O-glycosyl compound - Glycosyl compound - Phenol ether - Resorcinol - Phenoxy compound - Styrene - Methoxybenzene - Anisole - 1-hydroxy-2-unsubstituted benzenoid - Phenol - 1-hydroxy-4-unsubstituted benzenoid - Alkyl aryl ether - Oxane - Benzenoid - Monosaccharide - Monocyclic benzene moiety - Secondary alcohol - Acetal - Oxacycle - Ether - Organoheterocyclic compound - Polyol - Alcohol - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as stilbene glycosides. These are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.
• External Descriptors: Not available

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (237.86 mM; Need ultrasonic)
• Sensitivity: Light sensitive
• Molecular Weight: 420.400 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 420.142 Da
• Monoisotopic Mass: 420.142 Da
• Topological Polar Surface Area: 149.000 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 549.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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