Structure Database (LMSD)

Common Name
Casticin
Systematic Name
3,6,7,4'-Tetra-O-methyl-5,3'-dihydroxyflavone
Synonyms
  • Quercetagetin 3,6,7,4'-tetramethyl ether
LM ID
LMPK12113010
Formula
C19H18O8
Exact Mass
Calculate m/z
374.10017
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]
Flavones and Flavonols [PK1211]

Biological Context

Casticin is a flavonol isolated from A. annua, V. trifolia, and V. agnus-castus that decreases proliferation in K562, HL-60, and Kasumi-1 leukemia cell lines (IC50s = 5.95, 4.82, and 15.56 µM, respectively).1 It blocks TGF-β/SMAD signaling in LX2 cells preventing activation, inhibiting proliferation, and inducing apoptosis of these hepatic stellate cells.2 In a mouse model of liver fibrosis, casticin (20 mg/kg) decreases TGF-β1 mRNA and phosphorylated SMAD (p-SMAD) levels. Casticin induces apoptosis in hepatocellular carcinoma (HCC) and breast cancer cells.3,4 It also downregulates Twist and prevents the epithelial-mesenchymal transition (EMT) in human HCC SMMC-7721 cells.5

This information has been provided by Cayman Chemical

References

1. Zhou, L., Dong, X., Wang, L., et al. Casticin attenuates liver fibrosis and hepatic stellate cell activation by blocking TGF-β/Smad signaling pathway. Oncotarget (2017).
2. Shen, J.-K., Du, H.-P., Yang, M., et al. Casticin induces leukemic cell death through apoptosis and mitotic catastrophe. Ann. Hematol. 88(8), 743-752 (2009).
3. He, M., Cao, X.C., He, G.C., et al. Casticin inhibits epithelial-mesenchymal transition of liver cancer stem cells of the SMMC-7721 cell line through downregulating Twist. Oncol. Lett. 7(5), 1625-1631 (2014).
4. Liu, L.P., Cao, X.C., Liu, F., et al. Casticin induces breast cancer cell apoptosis by inhibiting the expression of forkhead box protein M1. Oncol. Lett. 7(5), 1711-1717 (2014).
5. Karim, Z.A., Zhang, J., Bangerjee, M., et al. IκB kinase phosphorylation of SNAP-23 controls platelet secretion. Blood 121(22), 4567-4574 (2013).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
PJQLSMYMOKWUJG-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C19H18O8/c1-23-11-6-5-9(7-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=C(O)C(OC)=CC=3)=C(OC)C(=O)C=2C(O)=C1OC

Other Databases

HMDB ID
HMDB0030660
CHEBI ID
69355
METABOLOMICS ID
FL5FECNS0029
PubChem CID
5315263
Cayman ID
16976

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 3
Aromatic Rings 3
Rotatable Bonds 5
Van der Waals Molecular Volume 316.68
Topological Polar Surface Area 107.59
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 8
logP 3.81
Molar Refractivity 97.57

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Updated at
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