Structure Database (LMSD)
Common Name
6-Prenylnaringenin
Systematic Name
Synonyms
3D model of 6-Prenylnaringenin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
(2S)-6-Prenylnaringenin is a prenylated flavonoid that has been found in the hop plant, H. lupulus, and has diverse biological activities.1,2 It inhibits the T-type voltage-gated calcium (Cav) channel Cav3.2 in HEK293 cells and high-voltage-activated calcium currents in differentiated NG 108-15 cells in whole-cell patch-clamp assays (IC50s = 0.928 and 2.005 µM, respectively).1 (2S)-6-Prenylnaringenin reduces the activity of aldose reductase 2 (ALR2; IC50 = 6.2 µM for the recombinant human enzyme).2 It reduces mechanical allodynia in a mouse model of sodium hydrosulfide-induced somatic pain when administered at a dose of 10 pmol/paw.1
This information has been provided by Cayman Chemical
References
2. Shim, S.H., Kim, Y., Lee, J.Y., et al. Aldose reductase inhibitory activity of the compounds from the seed of Psoralea corylifolia. J. Korean Soc. Appl. Biol. Chem. 52(5), 568–572 (2009).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
YHWNASRGLKJRJJ-KRWDZBQOSA-N
InChi (Click to copy)
InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-18-19(20(14)24)16(23)10-17(25-18)12-4-6-13(21)7-5-12/h3-7,9,17,21-22,24H,8,10H2,1-2H3/t17-/m0/s1
SMILES (Click to copy)
C1(O)C=C2O[C@]([H])(C3C=CC(O)=CC=3)CC(=O)C2=C(O)C=1C/C=C(\C)/C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
3
Aromatic Rings
2
Rotatable Bonds
3
Van der Waals Molecular Volume
318.51
Topological Polar Surface Area
89.06
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
4.02
Molar Refractivity
93.33
Admin
Created at
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Updated at
9th Jun 2022