Structure Database (LMSD)
Common Name
Isosakuranetin
Systematic Name
Synonyms
3D model of Isosakuranetin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Isosakuranetin is a flavanone that has been found in Citrus species and has diverse biological activities.1,2,3,4,5,6,7 It inhibits calcium uptake induced by pregnenolone sulfate (PregS) in HEK293 cells expressing mouse transient receptor potential melastatin 3 (TRPM3; IC50 = 50 nM).1 Isosakuranetin is selective for TRPM3 over TRPM1, TRPM8, and TRP vanilloid-related 1 (TRPV1) when used at a concentration of 10 μM. In vivo, isosakuranetin (2 mg/kg) increases latency to first pain-related response in mice in a hot plate test and reduces the number and duration of PregS-induced nocifensive responses, such as paw licking, shaking, or lifting, in mice. It also reduces systolic blood pressure in spontaneously hypertensive rats when administered at a dose of 10 mg/kg.2 Isosakuranetin (20 µM) inhibits UV-B-induced matrix metalloproteinase-1 (MMP-1) expression by 90% in HaCaT human keratinocyte cells, as well as phosphorylation of ERK1/2 when used at a concentration of 50 µM.3 It blocks hydrogen peroxide-induced increases in reactive oxygen species (ROS), intracellular calcium concentration, caspase-3 activity, and JNK phosphorylation, as well as decreases in catalase activity, in PC12 cells when used at a concentration of 0.8 µM.4 Isosakuranetin also has antibacterial and trypanocidal activity against M. tuberculosis, C. neoformans, and T. cruzi.5,6,7
This information has been provided by Cayman Chemical
References
5. da Silva Filho, A.A., de Sousa, J.P., Soares, S., et al. Antimicrobial activity of the extract and isolated compounds from Baccharis dracunculifolia D. C. (Asteraceae). Z. Naturforsch. C. 63(1-2), 40-46 (2008).
7. da Silva Filho, A.A., Pires Bueno, P.C., Gregório, L.E., et al. In-vitro trypanocidal activity evaluation of crude extract and isolated compounds from Baccharis dracunculifolia D.C. (Asteraceae). J. Pharm. Pharmacol. 56(9), 1195-1199 (2004).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
HMUJXQRRKBLVOO-AWEZNQCLSA-N
InChi (Click to copy)
InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1
SMILES (Click to copy)
C1(O)C=C2O[C@]([H])(C3C=CC(OC)=CC=3)CC(=O)C2=C(O)C=1
Other Databases
Wikipedia
KEGG ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
3
Aromatic Rings
2
Rotatable Bonds
2
Van der Waals Molecular Volume
251.95
Topological Polar Surface Area
78.06
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
5
logP
2.81
Molar Refractivity
75.08
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