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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
Structure of AURAPTENE

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+

HIDE SMILES / InChI

Molecular Formula C19H22O3
Molecular Weight 298.3762
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
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.

Originator

Sources: Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft (1938), 276, 482-8

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
23.9 µM [IC50]
345.1 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Suppression of beta-catenin mutation by dietary exposure of auraptene, a citrus antioxidant, in N,N-diethylnitrosamine-induced hepatocellular carcinomas in rats.
2005 Aug
Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1.
2008 Dec 14
Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice.
2009 Mar 28
Effects of selected food phytochemicals in reducing the toxic actions of TCDD and p,p'-DDT in U937 macrophages.
2010 Dec
Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata.
2010 Jul
Effects of Auraptene on IGF-1 Stimulated Cell Cycle Progression in the Human Breast Cancer Cell Line, MCF-7.
2012
Patents

Sample Use Guides

Auraptene was administrated to rats for 28 days by oral gavage in doses of 125 and 250 mg/kg.
Route of Administration: Oral
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:37:12 GMT 2023
Edited
by admin
on Fri Dec 15 18:37:12 GMT 2023
Record UNII
F79I1ZEL2E
Record Status Validated (UNII)
Record Version
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Name Type Language
AURAPTENE
Common Name English
7-GERANYLOXYCOUMARIN
Systematic Name English
7-(GERANYLOXY)COUMARIN
Systematic Name English
AURAPTEN
Common Name English
2H-1-BENZOPYRAN-2-ONE, 7-(((2E)-3,7-DIMETHYL-2,6-OCTADIEN-1-YL)OXY)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID80897576
Created by admin on Fri Dec 15 18:37:12 GMT 2023 , Edited by admin on Fri Dec 15 18:37:12 GMT 2023
PRIMARY
CHEBI
134355
Created by admin on Fri Dec 15 18:37:12 GMT 2023 , Edited by admin on Fri Dec 15 18:37:12 GMT 2023
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CAS
495-02-3
Created by admin on Fri Dec 15 18:37:12 GMT 2023 , Edited by admin on Fri Dec 15 18:37:12 GMT 2023
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FDA UNII
F79I1ZEL2E
Created by admin on Fri Dec 15 18:37:12 GMT 2023 , Edited by admin on Fri Dec 15 18:37:12 GMT 2023
PRIMARY
PUBCHEM
1550607
Created by admin on Fri Dec 15 18:37:12 GMT 2023 , Edited by admin on Fri Dec 15 18:37:12 GMT 2023
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WIKIPEDIA
AURAPTENE
Created by admin on Fri Dec 15 18:37:12 GMT 2023 , Edited by admin on Fri Dec 15 18:37:12 GMT 2023
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