Structure Database (LMSD)

Common Name
Artemetin
Systematic Name
Synonyms
  • Quercetagetin 3,6,7,3',4'-pentamethyl ether
LM ID
LMPK12113017
Formula
C20H20O8
Exact Mass
Calculate m/z
388.11582
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

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

Biological Context

Artemitin is a flavonoid that has been found in A. annua and has diverse biological activities.1,2,3,4,5 It scavenges peroxyl radicals in a cell-free assay in a concentration-dependent manner.1 Artemitin inhibits 5-lipoxygenase (5-LO) with an IC50 value of 54.6 µM.2 It is active against P. falciparum (IC50 = 26 µM).3 Artemitin is cytotoxic to HL-60 leukemia cells (IC50 = 30.98 µM).4 In vivo, artemitin (0.75 mg/kg) decreases mean arterial blood pressure in normotensive rats, as well as reduces angiotensin I-induced, but not angiotensin II-induced, increases in mean arterial blood pressure in rats.5

This information has been provided by Cayman Chemical

References

1. Liu, K.C., Yang, S.L., Roberts, M.F., et al. Antimalarial activity of Artemisia annua flavonoids from whole plants and cell cultures. Plant Cell Rep. 11(12), 637-640 (1992).
2. Dugas, A.J., Jr., Castañeda-Acosta, J., Bonin, G.C., et al. Evaluation of the total peroxyl radical-scavenging capacity of flavonoids: Structure-activity relationships. J. Nat. Prod. 63(3), 327-331 (2000).
3. Choudhary, M.I., Azizuddin, Jalil, S., et al. Antiinflammatory and lipoxygenase inhibitory compounds from Vitex agnus-castus. Phytother. Res. 23(9), 1336-1339 (2009).
4. Ko, W.G., Kang, T.H., Lee, S.J., et al. Polymethoxyflavonoids from Vitex rotundifolia inhibit proliferation by inducing apoptosis in human myeloid leukemia cells. Food Chem. Toxicol. 38(10), 861-865 (2000).
5. de Souza, P., Gasparotto, A., Jr., Crestani, S., et al. Hypotensive mechanism of the extracts and artemetin isolated from Achillea millefolium L. (Asteraceae) in rats. Phytomedicine. 18(10), 819-825 (2011).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
RIGYMJVFEJNCKD-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C20H20O8/c1-23-11-7-6-10(8-12(11)24-2)18-20(27-5)17(22)15-13(28-18)9-14(25-3)19(26-4)16(15)21/h6-9,21H,1-5H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=C(OC)C(OC)=CC=3)=C(OC)C(=O)C=2C(O)=C1OC

Other Databases

HMDB ID
HMDB0030095
CHEBI ID
175930
METABOLOMICS ID
FL5FECNS0036
PubChem CID
5320351
Cayman ID
40269

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 3
Aromatic Rings 3
Rotatable Bonds 6
Van der Waals Molecular Volume 333.98
Topological Polar Surface Area 96.59
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 8
logP 4.11
Molar Refractivity 102.45

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Updated at
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