Kaempferol 3-O-β-D-glucuronide - Moligand™, ≥98% , CAS No.22688-78-4

CAS: 22688-78-4 Cat. No.: K651503 Molecular Weight: 462.36 EC Number: 685-695-4 PubChem CID: 5318759

GRADE & PURITY Moligand™, ≥98%

Synonyms

EGG5MC7LNS | 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-D-glucopyranosiduronic acid | CHEBI:75721 | Kaempferol 3-O-beta-D-glucuronide | STK681025 | Kaempferol 3-O-beta-D-glucuronopyranoside | Kaempferol 3-glucuronide | HY-N7176 | kaempfe

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Kaempferol 3-O-β-D-glucuronide (Kaempferol-3-glucuronide), one conjugated kaempferol metabolite, has anti-inflammatory effect. Kaempferol 3-O-β-D-glucuronide significantly inhibits various pro-inflammatory mediators like IL-1β, NO, PGE2, and LTB4. Kaempferol 3-O-β-D-glucuronide upregulates the secretion of anti-inflammatory cytokine IL-10

Form:Solid

IC50& Target:IL-1β|IL-10

Specifications

Synonyms

EGG5MC7LNS | 5, 7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-D-glucopyranosiduronic acid | CHEBI:75721 | Kaempferol 3-O-beta-D-glucuronide | STK681025 | Kaempferol 3-O-beta-D-glucuronopyranoside | Kaempferol 3-glucuronide | HY-N7176 | kaempfe

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Kaempferol 3-O-β-D-glucuronide (Kaempferol-3-glucuronide), one conjugated kaempferol metabolite, has anti-inflammatory effect. Kaempferol 3-O-β-D-glucuronide significantly inhibits various pro-inflammatory mediators like IL-1β, NO, PGE2, and LTB4. Kaempfe

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

≥98%

Names and Identifiers

• Canonical Smiles: C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O
• IUPAC Name: (2S,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• InChIKey: FNTJVYCFNVUBOL-ZUGPOPFOSA-N
• INCHI: 1S/C21H18O12/c22-8-3-1-7(2-4-8)17-18(13(25)12-10(24)5-9(23)6-11(12)31-17)32-21-16(28)14(26)15(27)19(33-21)20(29)30/h1-6,14-16,19,21-24,26-28H,(H,29,30)/t14-,15-,16+,19-,21+/m0/s1
• Isomeric SMILES: C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O
• Alternate CAS: 22688-78-4
• PubChem CID: 5318759
• Molecular Weight: 462.36

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid O-glucuronides
            • Level7 Flavonoid-3-O-glucuronides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides - Flavonoid O-glucuronides
• Direct Parent: Flavonoid-3-O-glucuronides
• Alternative Parents: Flavonoid-3-O-glycosides 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavones O-glucuronides Hexoses O-glycosyl compounds Chromones 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Pyranones and derivatives Beta hydroxy acids and derivatives Oxanes Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Secondary alcohols Monocarboxylic acids and derivatives Acetals Oxacyclic compounds Polyols Carboxylic acids Carbonyl compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-3-o-glucuronide - Flavonoid-3-o-glycoside - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavone - Hydroxyflavonoid - 1-o-glucuronide - O-glucuronide - Glucuronic acid or derivatives - Hexose monosaccharide - Chromone - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Beta-hydroxy acid - Pyranone - Phenol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Pyran - Hydroxy acid - Monosaccharide - Oxane - Vinylogous acid - Heteroaromatic compound - Secondary alcohol - Monocarboxylic acid or derivatives - Acetal - Organoheterocyclic compound - Polyol - Oxacycle - Carboxylic acid derivative - Carboxylic acid - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Alcohol - Organic oxygen compound - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position.
• External Descriptors: trihydroxyflavone - kaempferol O-glucuronide

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

Chemical and Physical Properties

• Solubility: Ethanol: 1 mg/mL (2.16 mM), Sonication and heating to 37℃ are recommended. DMSO: 95 mg/mL (205.47 mM), Sonication is recommended.
• Sensitivity: Light sensitive
• Molecular Weight: 462.400 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 4
• Exact Mass: 462.08 Da
• Monoisotopic Mass: 462.08 Da
• Topological Polar Surface Area: 203.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 790.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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