Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H22O3 |
Molecular Weight | 298.3762 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)=CCC\C(C)=C\COC1=CC=C2C=CC(=O)OC2=C1
InChI
InChIKey=RSDDHGSKLOSQFK-RVDMUPIBSA-N
InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27771936Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22472691 | https://www.ncbi.nlm.nih.gov/pubmed/23047230 | https://www.ncbi.nlm.nih.gov/pubmed/22222157 | https://www.ncbi.nlm.nih.gov/pubmed/29080847
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27771936
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22472691 | https://www.ncbi.nlm.nih.gov/pubmed/23047230 | https://www.ncbi.nlm.nih.gov/pubmed/22222157 | https://www.ncbi.nlm.nih.gov/pubmed/29080847
Auraptene (7-Geranyloxycoumarin) is the best known and most abundant prenyloxycoumarin present in nature. It is synthesized by various plant species, mainly those of the Rutaceae and Umbelliferae (Apiaceae) families, comprising many edible fruits and vegetables such as lemons, grapefruit, and orange. Auraptene has shown a remarkable effect in the prevention of degenerative diseases, in particular, it has been reported to be one the most promising known natural chemopreventive agents against several types of cancer. The effect in humans is not yet known.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2047 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22472691 |
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Target ID: CHEMBL2903 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23047230 |
23.9 µM [IC50] | ||
Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22222157 |
345.1 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1. | 2008 Dec 14 |
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Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice. | 2009 Mar 28 |
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Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata. | 2010 Jul |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29080847
Auraptene was administrated to rats for 28 days by oral gavage in doses of 125 and 250 mg/kg.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28675489
HT29 cells were used for activity evaluation. To study the cytotoxicity of auraptene in combination with chemotherapy or ionizing radiation, thiazolyl blue (MTT) assay was used. In this regard, MTT dye (Atocel, Budapest, Hungary) was dissolved in phosphate-buffered saline (PBS; 5 mg/mL) and added to each well (20 μL/well) by the end of treatments. Afterwards, plates were incubated for 4 h at 37°C, and then medium was replaced by DMSO (150 μL/well) to dissolve produced formazan crystals, and finally, optic densities of wells were measured spectrophotometrically at 570 nm using an ELISA plate reader (Awareness Connecticut, USA).
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DTXSID80897576
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134355
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495-02-3
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F79I1ZEL2E
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1550607
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AURAPTENE
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SUBSTANCE RECORD