Structure Database (LMSD)

Common Name
Irisflorentin
Systematic Name
5,3',4',5'-Tetramethoxy-6,7-methylenedioxyisoflavone
Synonyms
LM ID
LMPK12050419
Formula
Exact Mass
Calculate m/z
386.10017
Status
Curated

Classification

Biological Context

Irisflorentin is an isoflavone that has been found in B. chinensis and has anti-inflammatory and cytoprotective activities.1,2,3 It reduces LPS-induced increases in the levels of nitric oxide (NO), inducible NO synthase (iNOS), TNF-α, IL-1β, and IL-6 in RAW 264.7 macrophages at 10, 20, and 40 µM.1 Irisflorentin increases phagocytosis of E. coli by RAW 264.7 macrophages at 40 µM and prevents M1 polarization in mouse bone marrow-derived macrophages (BMDMs).2 It also reduces the secretion of IL-6, TNF-α, and IL-10 induced by heat-inactivated methicillin-resistant S. aureus (HK-MRSA) in mouse BMDMs. Irisflorentin activates the PI3K, mTOR, and BDNF signaling pathways, increases cell viability, and reduces lactate dehydrogenase (LDH) release, reactive oxygen species (ROS) production, and apoptosis in a PC12 cellular model of ischemic stroke using oxygen-glucose deprivation and reoxygenation.3

This information has been provided by Cayman Chemical

References

3. Y., Z., Lu, T., Luo, X., et al. Elucidating the mechanism of anti-ischemic stroke action of Irisflorentin: A combined approach using network pharmacology, molecular docking, and in vitro validation. Eur. J. Med. Chem. Rep. 16, 1000318 (2026).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/
Magnoliopsida (#3398)
Studies on Constituents of Iris Genus Plants. IV. The Constituents of Iris florentina L.,
Chem Pharm Bull (Tokyo), 1973

String Representations

InChiKey (Click to copy)
RISXUTCDCPHJFQ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C20H18O8/c1-22-13-5-10(6-14(23-2)18(13)24-3)11-8-26-12-7-15-19(28-9-27-15)20(25-4)16(12)17(11)21/h5-8H,9H2,1-4H3
SMILES (Click to copy)
C12OCOC1=C(OC)C1C(=O)C(C3C=C(OC)C(OC)=C(OC)C=3)=COC=1C=2

Other Databases

KEGG ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 4
Aromatic Rings 3
Rotatable Bonds 5
Van der Waals Molecular Volume 321.62
Topological Polar Surface Area 89.73
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 8
logP 4.12
Molar Refractivity 100.36

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Created at
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Updated at
3rd Jun 2025