Structure Database (LMSD)

Common Name
Tamarixetin
Systematic Name
3,3',5,7-Tetrahydroxy-4'-methoxyflavone
Synonyms
  • 4'-O-Methylquercetin
LM ID
LMPK12110606
Formula
C16H12O7
Exact Mass
Calculate m/z
316.058305
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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

4'-O-methyl Quercetin is a flavonoid isolated from C. ordata with anticancer and antiplasmodial activity.1,2,3 4'-O-methyl Quercetin is a major metabolite of quercetin that inhibits the viability of HL-60, U937, MOLT-3, Raji, K562, MCF-7, SK-MEL-1, and A549 human tumor cell lines with IC50 values ranging from 5.5-24.1 μM.1 It induces G2-M arrest and inhibits tubulin polymerization in vitro in a dose-dependent manner. 4'-O-methyl Quercetin inhibits breast cancer resistance protein (BCRP/ABCG2; IC50 = 40 nM in a vesicular transport assay) with no cellular toxicity indicating potential for use in overcoming multidrug resistance in chemotherapy.2 4'-O-methyl Quercetin also reduces in vitro proliferation of chloroquine-resistant P. falciparum (IC50 = 4.8 μM) and suppresses infection in mice (65-81% suppression at 2.5-5 mg/kg dose).3

This information has been provided by Cayman Chemical

References

1. Nicolini, F., Burmistrova, O., Marrero, M.T., et al. Induction of G2/M phase arrest and apoptosis by the flavonoid tamarixetin on human leukemia cells. mol. Carcinog. 53(12), 939-950 (2014).
2. Tan, K.W., Li, Y., Paxton, J.W., et al. Identification of novel dietary phytochemicals inhibiting the efflux transporter breast cancer resistance protein (BCRP/ABCG2). Food Chem. 138(4), 2267-2274 (2013).
3. Ezenyi, I.C., Salawu, O.A., Kulkarni, R., et al. Antiplasmodial activity-aided isolation and identification of quercetin-4'-methyl ether in Chromolaena odorata leaf fraction with high activity against chloroquine-resistant Plasmodium falciparum. Parasitol Res. 113(12), 4415-4422 (2014).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
FPLMIPQZHHQWHN-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O7/c1-22-11-3-2-7(4-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
SMILES (Click to copy)
C1(O)=CC2OC(C3C=C(O)C(OC)=CC=3)=C(O)C(=O)C=2C(O)=C1

Other Databases

Wikipedia
Tamarixetin
KEGG ID
C10188
CHEBI ID
67492
METABOLOMICS ID
FL5FAENS0001
PubChem CID
5281699
Cayman ID
22406

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 3
Aromatic Rings 3
Rotatable Bonds 2
Van der Waals Molecular Volume 255.99
Topological Polar Surface Area 120.36
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 7
logP 3.19
Molar Refractivity 81.24

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Updated at
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