isoliquiritin apioside - analytical standard , CAS No.120926-46-7

CAS: 120926-46-7 Cat. No.: I302628 Molecular Weight: 550.509

GRADE & PURITY Analytical standard

Synonyms

CHEBI:191794 | (E)-3-(4-(((2S,3R,4S,5S,6R)-3-(((2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-1-(2,4-dihydroxyphenyl)prop-2-en-1-one | MFCD20487832 | Neolicuroside |

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Isoliquiritin apioside, a component isolated from Glycyrrhizae radix rhizome, significantly decreases PMA-induced increases in MMP9 activities and suppresses PMA-induced activation of MAPK and NF-κB. Isoliquiritin apioside auppresseses invasiveness and angiogenesis of cancer cells and endothelial cells.

Specifications

Synonyms

CHEBI:191794 | (E)-3-(4-(((2S, 3R, 4S, 5S, 6R)-3-(((2S, 3R, 4R)-3, 4-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-4, 5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-1-(2, 4-dihydroxyphenyl)prop-2-en-1-one | MFCD20487832 | Neolicuroside |

Specifications & Purity

analytical standard

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

Analytical standard

Names and Identifiers

• Canonical Smiles: C1C(C(C(O1)OC2C(C(C(OC2OC3=CC=C(C=C3)C=CC(=O)C4=C(C=C(C=C4)O)O)CO)O)O)O)(CO)O
• IUPAC Name: (E)-3-[4-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1-(2,4-dihydroxyphenyl)prop-2-en-1-one
• InChIKey: VMMVZVPAYFZNBM-KVFWHIKKSA-N
• INCHI: 1S/C26H30O13/c27-10-19-20(32)21(33)22(39-25-23(34)26(35,11-28)12-36-25)24(38-19)37-15-5-1-13(2-6-15)3-8-17(30)16-7-4-14(29)9-18(16)31/h1-9,19-25,27-29,31-35H,10-12H2/b8-3+/t19-,20-,21+,22-,23+,24-,25+,26-/m1/s1
• Isomeric SMILES: C1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC=C(C=C3)/C=C/C(=O)C4=C(C=C(C=C4)O)O)CO)O)O)O)(CO)O
• Molecular Weight: 550.509
• Reaxy-Rn: 54622471
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=54622471&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavonoid O-glycosides
• Alternative Parents: 2'-Hydroxychalcones Cinnamylphenols Phenolic glycosides Disaccharides O-glycosyl compounds Aryl ketones Benzoyl derivatives Styrenes Phenol ethers Phenoxy compounds Resorcinols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Oxanes Tertiary alcohols Enones Acryloyl compounds Vinylogous acids Tetrahydrofurans Secondary alcohols Oxacyclic compounds Acetals Hydrocarbon derivatives Organic oxides Primary alcohols
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Flavonoid o-glycoside - 2'-hydroxychalcone - Linear 1,3-diarylpropanoid - Phenolic glycoside - Cinnamylphenol - Disaccharide - Glycosyl compound - O-glycosyl compound - Benzoyl - Phenoxy compound - Phenol ether - Resorcinol - Styrene - Aryl ketone - Phenol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Oxane - Vinylogous acid - Alpha,beta-unsaturated ketone - Tetrahydrofuran - Tertiary alcohol - Acryloyl-group - Enone - Secondary alcohol - Ketone - Oxacycle - Organoheterocyclic compound - Acetal - Organooxygen compound - Alcohol - Primary alcohol - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonoid o-glycosides. These are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
• 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

Chemical and Physical Properties

• Molecular Weight: 550.500 g/mol
• XLogP3: 0.100
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 9
• Exact Mass: 550.169 Da
• Monoisotopic Mass: 550.169 Da
• Topological Polar Surface Area: 216.000 Ų
• Heavy Atom Count: 39
• Formal Charge: 0
• Complexity: 833.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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