Structure Database (LMSD)

Common Name
Isosakuranetin
Systematic Name
Synonyms
LM ID
LMPK12140355
Formula
Exact Mass
Calculate m/z
286.084125
Status
Curated



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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