Icariside I - analytical standard , CAS No.56725-99-6

CAS: 56725-99-6 Cat. No.: I399232 Formula: C₂₇H₃₀O₁₁ Molecular Weight: 530.52

GRADE & PURITY Analytical standard

Synonyms

3,5,7-Trihydroxy-4'-methoxy-8'-prenylflavone-3-O-alpha-L-rhamnopranoxide | icariside 1 | 3,5-Dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one | s3

Storage

Store at 2-8°C,Desiccated

Shipped In

Wet ice

Specifications

Synonyms

3,5,7-Trihydroxy-4'-methoxy-8'-prenylflavone-3-O-alpha-L-rhamnopranoxide | icariside 1 | 3,5-Dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one | s3

Specifications & Purity

analytical standard

Storage

Store at 2-8°C,Desiccated

Shipped In

Wet ice

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

Grade

Analytical standard

Names and Identifiers

Pubchem Sid

508814511

Canonical Smiles

CC(=CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)OC)O)OC4C(C(C(C(O4)CO)O)O)O)C

IUPAC Name

3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

InChIKey

IYCPMVXIUPYNHI-WPKKLUCLSA-N

INCHI

1S/C27H30O11/c1-12(2)4-9-15-17(36-27-24(34)22(32)20(30)18(11-28)37-27)10-16(29)19-21(31)23(33)25(38-26(15)19)13-5-7-14(35-3)8-6-13/h4-8,10,18,20,22,24,27-30,32-34H,9,11H2,1-3H3/t18-,20-,22+,24-,27-/m1/s1

Isomeric SMILES

CC(=CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)OC)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C

Molecular Weight

530.52

Reaxy-Rn

38880422

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=38880422&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-7-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides
• Direct Parent: Flavonoid-7-O-glycosides
• Alternative Parents: 8-prenylated flavones 4'-O-methylated flavonoids Flavonols 3-hydroxyflavonoids 5-hydroxyflavonoids Phenolic glycosides Hexoses Chromones O-glycosyl compounds Anisoles Phenoxy compounds Methoxybenzenes 1-hydroxy-2-unsubstituted benzenoids Pyranones and derivatives Alkyl aryl ethers Oxanes Vinylogous acids Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Polyols Acetals Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-7-o-glycoside - 8-prenylated flavone - 4p-methoxyflavonoid-skeleton - 3-hydroxyflavone - 3-hydroxyflavonoid - 5-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Phenolic glycoside - Hexose monosaccharide - Chromone - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Pyranone - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Pyran - Oxane - Benzenoid - Monosaccharide - Monocyclic benzene moiety - Vinylogous acid - Heteroaromatic compound - Secondary alcohol - Polyol - Ether - Organoheterocyclic compound - Acetal - Oxacycle - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Alcohol - Primary alcohol - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
• 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

• Molecular Weight: 530.500 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 530.179 Da
• Monoisotopic Mass: 530.179 Da
• Topological Polar Surface Area: 175.000 Ų
• Heavy Atom Count: 38
• Formal Charge: 0
• Complexity: 891.000
• 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