Structure Database (LMSD)

Common Name
Isoxanthohumol(Sophora)
Systematic Name
Synonyms
LM ID
LMPK12140553
Formula
C21H22O5
Exact Mass
Calculate m/z
354.146725
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavanones [PK1214]

Biological Context

Isoxanthohumol is a natural, prenylated chalcone isolated from the hop plant, H. lupulus (hops). It has diverse biological activities, including antiproliferative, anti-inflammatory, and antiviral properties.1 In B16 and A375 melanoma cells, isoxanthohumol inhibits proliferation (IC50s = 22.15 and 22.9 µM in an MTT assay), slows cell division, and induces apoptosis.2 Isoxanthohumol reversibly inhibits Kv1.3 channels with an EC50 value of 7.8 µM in human Jurkat T cells using patch clamp electrophysiology.3 It has also been used as a marker of beer consumption.4 Isoxanthohumol is metabolized in the liver and intestine to 8-prenylnaringenin , a potent phytoestrogen.4

This information has been provided by Cayman Chemical

References

1. Żołnierczyk, A.K., Mączka, W.K., Grabarczyk, M., et al. Isoxanthohumol--Biologically active hop flavonoid. Fitoterapia 103, 71-82 (2015).
2. Quifer-Rada, P., Martínez-Huélamo, M., Chiva-Blanch, G., et al. Urinary isoxanthohumol is a specific and accurate biomarker of beer consumption. J. Nutr. 144(4), 484-488 (2014).
3. Krajnović, T., Kaluđerović, G.N., Wessjohann, L.A., et al. Versatile antitumor potential of isoxanthohumol: Enhancement of paclitaxel activity in vivo. Pharmacol. Res. 105, 62-73 (2016).
4. Gąsiorowska, J., Teisseyre, A., Uryga, A., et al. Inhibition of Kv1.3 channels in human jurkat T cells by xanthohumol and isoxanthohumol. J. Membr. Biol. 248(4), 705-711 (2015).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)
YKGCBLWILMDSAV-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3
SMILES (Click to copy)
C1(O)=C(C/C=C(/C)\C)C2OC(C3C=CC(O)=CC=3)CC(=O)C=2C(OC)=C1

Other Databases

CHEBI ID
171798
METABOLOMICS ID
FL2FBANI0001
PubChem CID
513197
Cayman ID
23233

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 3
Aromatic Rings 2
Rotatable Bonds 4
Van der Waals Molecular Volume 335.81
Topological Polar Surface Area 78.06
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 4.32
Molar Refractivity 98.22

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Updated at
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