Structure Database (LMSD)

Common Name
Xanthohumol
Systematic Name
Synonyms
LM ID
LMPK12120294
Formula
C21H22O5
Exact Mass
Calculate m/z
354.146725
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Chalcones and dihydrochalcones [PK1212]

Biological Context

Xanthohumol is a natural prenylated chalcone isolated from the hop plant, H. lupulus. Xanthohumol and its metabolites induce protective detoxification enzymes, at least in part via the nuclear factor erythroid-2-related factor 2 pathway.1,2 It inhibits phosphoinositide-dependent kinase 1 (IC50 = 6.6 μM) but not PKC in an in vitro assay.3 Xanthohumol also can have anti-inflammatory, antioxidant, anti-carcinogenic, and osteogenic effects.4,5,6

This information has been provided by Cayman Chemical

References

1. Costa, R., Negrao, R., Valente, I., et al. Xanthohumol modulates inflammation, oxidative stress, and angiogenesis in type 1 diabetic rat skin wound healing. J. Nat. Prod. 76(11), 2047-2053 (2013).
2. Venè, R., Benelli, R., Minghelli, S., et al. Xanthohumol impairs human prostate cancer cell growth and invasion and diminishes the incidence and progression of advanced tumors in TRAMP mice. Mol. Med. 18(1), 1292-1302 (2012).
3. Schilling, T., Ebert, R., Raaijmakers, N., et al. Effects of phytoestrogens and other plant-derived compounds on mesenchymal stem cells, bone maintenance and regeneration. J. Steroid Biochem. Mol. Biol. 139, 252-261 (2014).
4. Lauro, G., Masullo, M., Piacente, S., et al. Inverse virtual screening allows the discovery of the biological activity of natural compounds. Bioorg. Med. Chem. 20(11), 3596-3602 (2012).
5. Krajka-Kuzniak, V., Paluszczak, J., and Baer-Dubowska, W. Xanthohumol induces phase II enzymes via Nrf2 in human hepatocytes in vitro. Toxicol. In Vitro 27(1), 149-156 (2013).
6. Dietz, B.M., and Bolton, J.L. Biological reactive intermediates (BRIs) formed from botanical dietary supplements. Chem. Biol. Interact. 192(1-2), 72-80 (2011).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
ORXQGKIUCDPEAJ-YRNVUSSQSA-N
InChi (Click to copy)
InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
SMILES (Click to copy)
C1=CC(O)=CC=C1/C=C/C(=O)C1C(O)=C(C/C=C(\C)/C)C(O)=CC=1OC

Other Databases

Wikipedia
Xanthohumol
KEGG ID
C16417
HMDB ID
HMDB0037479
CHEBI ID
66331
METABOLOMICS ID
FL1CBANI0001
PubChem CID
639665
Cayman ID
15399

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 2
Aromatic Rings 2
Rotatable Bonds 6
Van der Waals Molecular Volume 345.53
Topological Polar Surface Area 86.99
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 4.22
Molar Refractivity 100.93

Admin

Created at
-
Updated at
-