Structure Database (LMSD)

Common Name
Cirsiliol
Systematic Name
Synonyms
LM ID
LMPK12111227
Formula
C17H14O7
Exact Mass
Calculate m/z
330.073955
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavones and Flavonols [PK1211]

Biological Context

Cirsiliol is a flavonoid that has been found in S. indicum and has diverse biological activities.1 It inhibits 5-lipoxygenase (5-LO) and 12-LO (IC50s = 0.1 and 1 µM, respectively).1 Cirsiliol inhibits the release of slow-reacting substance of anaphylaxis (SRS-A) in passively sensitized isolated guinea pig lung (IC50 = 0.4 µM). It induces relaxation of precontracted isolated rat uterus, urinary bladder, proximal aorta, and trachea in a concentration-dependent manner.2 Cirsiliol inhibits colony formation and migration of B16/F10 murine melanoma cells.3 In vivo, cirsiliol (200 µg/kg) enhances radiation-induced inhibition of tumor growth in an H1299 non-small cell lung cancer (NSCLC) mouse xenograft model.4

This information has been provided by Cayman Chemical

References

1. Yoshimoto, T., Furukawa, M., Yamamoto, S., et al. Flavonoids: Potent inhibitors of arachidonate 5-lipoxygenase. Biochem. Biophys. Res. Commun. 116(2), 612-618 (1983).
2. Mustafa, E.H., Zarga, M.A., Sabri, S., et al. Effects of cirsiliol, a flavone isolated from Achillea fragrantissima, on rat isolated smooth muscle. Int. J. Pharm. 33(3), 204-209 (1995).
3. Prasad, P., Vasas, A., Hohmann, J., et al. Cirsiliol suppressed epithelial to mesenchymal transition in B16F10 malignant melanoma cells through alteration of the PI3K/Akt/NF-κB signaling pathway. Int. J. Mol. Sci. 20(3), 608 (2019).
4. Kang, J., Kim, E., Kim, W., et al. Rhamnetin and cirsiliol induce radiosensitization and inhibition of epithelial-mesenchymal transition (EMT) by miR-34a-mediated suppression of Notch-1 expression in non-small cell lung cancer cell lines. The Journal of Biological Chemisty 288(38), 27343-27357 (2013).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
IMEYGBIXGJLUIS-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=CC(O)=C(O)C=3)=CC(=O)C=2C(O)=C1OC

Other Databases

KEGG ID
C10033
CHEBI ID
3719
METABOLOMICS ID
FL3FECNS0001
PubChem CID
160237
Cayman ID
30874

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 3
Aromatic Rings 3
Rotatable Bonds 3
Van der Waals Molecular Volume 273.29
Topological Polar Surface Area 109.36
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 3.49
Molar Refractivity 86.13

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Updated at
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