Icariin - ≥96% , CAS No.489-32-7

CAS: 489-32-7 Cat. No.: I141014 Formula: C₃₃H₄₀O₁₅ Molecular Weight: 676.66 EC Number: 610-440-0 PubChem CID: 5318997

GRADE & PURITY ≥96%

Synonyms

3-((6-Deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one | 5-HYDROXY-2-(4-METHOXYPHENYL)-8-(3-METHYLBUT-2-EN-1-YL)-7-{[3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}-3-[(3,4,5-TRIHYD

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

3-((6-Deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one | 5-HYDROXY-2-(4-METHOXYPHENYL)-8-(3-METHYLBUT-2-EN-1-YL)-7-{[3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}-3-[(3,4,5-TRIHYD

Specifications & Purity

≥96%

Biochemical and Physiological Mechanisms

Selective cGMP specific PDE5 inhibitor (IC 50 = 0.4 and 74 μM for PDE5 and PDE4 respectively). Shows anti-inflammatory and antitumor effects in vivo . Orally active.

Storage

Room temperature

Shipped In

Normal

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥96%

Names and Identifiers

Pubchem Sid

488195337

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488195337

Canonical Smiles

COc1ccc(cc1)C2=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C(=O)c4c(O)cc(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)c(C\C=C(\C)C)c4O2

IUPAC Name

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

InChIKey

TZJALUIVHRYQQB-XLRXWWTNSA-N

INCHI

1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1

Isomeric SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O

WGK Germany

3

PubChem CID

5318997

Molecular Weight

676.66

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 Flavonoid-3-O-glycosides 4'-O-methylated flavonoids 5-hydroxyflavonoids Phenolic glycosides Chromones O-glycosyl compounds Anisoles Methoxybenzenes Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Pyranones and derivatives Monosaccharides Oxanes Vinylogous acids Heteroaromatic compounds Secondary alcohols Polyols Acetals Oxacyclic compounds Hydrocarbon derivatives Primary alcohols Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 8-prenylated flavone - Flavonoid-3-o-glycoside - Flavonoid-7-o-glycoside - 4p-methoxyflavonoid-skeleton - Hydroxyflavonoid - Flavone - 5-hydroxyflavonoid - Phenolic glycoside - Glycosyl compound - O-glycosyl compound - Chromone - Benzopyran - 1-benzopyran - Methoxybenzene - Phenol ether - Phenoxy compound - Anisole - Alkyl aryl ether - Pyranone - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Pyran - Monosaccharide - Oxane - Benzenoid - Heteroaromatic compound - Vinylogous acid - Secondary alcohol - Acetal - Oxacycle - Organoheterocyclic compound - Polyol - Ether - Organic oxide - Organic oxygen compound - Primary alcohol - Alcohol - Hydrocarbon derivative - Organooxygen 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: Flavones and Flavonols

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)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

Discover Target: PDE5A

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

POLB Tchem DNA polymerase beta (23632 Activities)

Discover Target: POLB

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

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

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

KDM1A Tchem Lysine-specific histone demethylase 1 (3916 Activities)

Discover Target: KDM1A

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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

IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

Discover Target: IDH1

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Associated Targets(non-human)

PDE6C Phosphodiesterase 6C (1 Activities)

Discover Target: PDE6C

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat Sensitive
• Specific Rotation[α]: -84° (C=1,Pyridine)
• Melt Point(°C): 235 - 239°C
• Molecular Weight: 676.700 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 9
• Exact Mass: 676.237 Da
• Monoisotopic Mass: 676.237 Da
• Topological Polar Surface Area: 234.000 Ų
• Heavy Atom Count: 48
• Formal Charge: 0
• Complexity: 1170.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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