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Icariside I (Standard)

CAT: 0804-HY-N1939R-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N1939R-01Size:5 mg
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Description
Icariside I (Standard) is the analytical standard of Icariside I. This product is intended for research and analytical applications. Icariside I (GH01) is an orally active metabolite of icalin. Icariside I improves estrogen deficiency-induced osteoporosis by simultaneously regulating osteoblast and osteoclast differentiation. Icariside I promotes ATP (HY-B2176) or Nigericin (HY-127019) -induced mtROS production and NLRP3 inflammasome activation and causes idiosyncratic hepatotoxicity. Icariside I does not alter the activation of NLRC4 and AIM2 inflammasomes. Icariside I inhibits breast cancer proliferation, apoptosis, invasion, and metastasis by targeting the IL-6/STAT3 pathway. Icariside I is a kynurenine-AhR pathway inhibitor that alleviates cancer by blocking tumor immune escape[1][2][3][4].
CAS Number
56725-99-6
Product Name Alternative
Icarisid I (Standard)
UNSPSC
12352005
Target
Apoptosis; Aryl Hydrocarbon Receptor; Bcl-2 Family; Caspase; CDK; IFNAR; JAK; NOD-like Receptor (NLR) ; PD-1/PD-L1; Reactive Oxygen Species (ROS) ; Reference Standards; STAT
Type
Reference Standards
Related Pathways
Apoptosis; Cell Cycle/DNA Damage; Epigenetics; Immunology/Inflammation; JAK/STAT Signaling; Metabolic Enzyme/Protease; NF-κB; Others; Protein Tyrosine Kinase/RTK; Stem Cell/Wnt
Field of Research
Cancer; Endocrinology; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/icariside-i-standard.html
Smiles
O=C1C(O)=C(C2=CC=C(OC)C=C2)OC3=C(C/C=C(C)\C)C(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)=CC(O)=C13
Molecular Formula
C27H30O11
Molecular Weight
530.52
References & Citations
[1]Gao Y, et al. Icariside I specifically facilitates ATP or nigericin-induced NLRP3 inflammasome activation and causes idiosyncratic hepatotoxicity. Cell Commun Signal. 2021 Feb 11;19 (1) :13.|[2]Hou M, et al. Icariside I reduces breast cancer proliferation, apoptosis, invasion, and metastasis probably through inhibiting IL-6/STAT3 signaling pathway. J Pharm Pharmacol. 2024 May 3;76 (5) :499-513. |[3]Chen G, et al. Icariside I - A novel inhibitor of the kynurenine-AhR pathway with potential for cancer therapy by blocking tumor immune escape. Biomed Pharmacother. 2022 Sep;153:113387.|[4]Chen C, et al. A Novel Prenylflavonoid Icariside I Ameliorates Estrogen Deficiency-Induced Osteoporosis via Simultaneous Regulation of Osteoblast and Osteoclast Differentiation. ACS Pharmacol Transl Sci. 2023 Jan 13;6 (2) :270-280.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards
Isoform
NLRP3

Chemical Information

Icariside I

Icariside I has been reported in Epimedium brevicornu, Epimedium truncatum, and other organisms with data available.

CAS Number56725-99-6
PubChem CID5745470
IUPAC Name3,5-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
Molecular FormulaC27H30O11
Molecular Weight530.5
XLogP3
Topological Polar Surface Area175
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count11
Rotatable Bond Count7
Heavy Atom Count38
Formal Charge0
Complexity891
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
InChI
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
InChIKey
IYCPMVXIUPYNHI-WPKKLUCLSA-N
Chemical Structure
2D Structure
2D structure of Icariside I
CAS: 56725-99-6
CID: 5745470
Formula: C27H30O11
MW: 530.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight530.5
XLogP33
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count11
Rotatable Bond Count7
Exact Mass530.17881177
Monoisotopic Mass530.17881177
Topological Polar Surface Area175 Ų
Heavy Atom Count38
Formal Charge0
Complexity891
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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