Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H10O5 |
| Molecular Weight | 246.2155 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2OC(=O)C=CC2=C(OC)C3=C1OC=C3
InChI
InChIKey=DFMAXQKDIGCMTL-UHFFFAOYSA-N
InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3
| Molecular Formula | C13H10O5 |
| Molecular Weight | 246.2155 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12376476 | https://www.ncbi.nlm.nih.gov/pubmed/28556437 | https://www.ncbi.nlm.nih.gov/pubmed/25240925
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12376476 | https://www.ncbi.nlm.nih.gov/pubmed/28556437 | https://www.ncbi.nlm.nih.gov/pubmed/25240925
Isopimpinellin is a natural product synthesized by Umbelliferae (or Apiaceae), also known as the carrot or parsley family. It can be found in celery, garden angelica, parsnip, fruits and in the rind and pulp of limes. There have been several studies looking into the effects of Isopimpinellin and other so-called naturally occurring coumarins (such as bergamottin and Imperatorin) as anticarcinogens.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins. | 2013-05-02 |
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| Aggressive mammary carcinoma progression in Nrf2 knockout mice treated with 7,12-dimethylbenz[a]anthracene. | 2010-10-08 |
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| Naturally occurring food toxins. | 2010-09 |
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| Application of the concept of relative photomutagenic potencies to selected furocoumarins in V79 cells. | 2010-03 |
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| Simultaneous and sensitive determination of xanthotoxin, psoralen, isoimpinellin and bergapten in rat plasma by liquid chromatography-electrospray ionization mass spectrometry. | 2010-02-15 |
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| Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats. | 2009-07-29 |
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| Botanical origin of Indian celery seed (fruit). | 2009-07 |
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| [Chemical constituents of fresh celery]. | 2009-06 |
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| Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice. | 2009-03-28 |
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| Osthol and isopimpinellin from Fructus cnidii for the control of Dactylogyrus intermedius in Carassius auratus. | 2008-11-25 |
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| Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice. | 2008-10-15 |
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| In vitro antiplasmodial activity of extract and constituents from Esenbeckia febrifuga, a plant traditionally used to treat malaria in the Brazilian Amazon. | 2008-05 |
|
| Identification of Ruta graveolens L. metabolites accumulated in the presence of abiotic elicitors. | 2007-12-07 |
|
| [Simultaneous determination of 5 active components in Fructus Cnidii by HPLC]. | 2007-09 |
|
| [Studies on the chemical constituents of the aerial parts of Seseli mairei]. | 2007-01 |
|
| [Inhibitory effects of 11 coumarin compounds against growth of human bladder carcinoma cell line E-J in vitro]. | 2007-01 |
|
| [Studies on chemical constituents from fruits of Paliurus ramosissimus]. | 2006-12 |
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| Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland. | 2006-06 |
|
| Cytochrome P450-mediated metabolism of xanthotoxin by Papilio multicaudatus. | 2006-03 |
|
| [Studies on chemical constituents in roots of Heracleum rapula]. | 2006-02 |
|
| Accumulation of biologically active furanocoumarins in agitated cultures of Ruta graveolens L. and Ruta graveolens ssp. divaricata (Tenore) Gams. | 2005-08 |
|
| Melanogenesis stimulation in murine b16 melanoma cells by umberiferae plant extracts and their coumarin constituents. | 2005-07 |
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| Coumarins are competitive inhibitors of cytochrome P450 1B1, with equal potency for allelic variants. | 2005-03 |
|
| Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes. | 2005-02-15 |
|
| Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture. | 2005-01 |
|
| [Quantification of isopimpinellin in root of Toddalia asiatica by HPLC]. | 2004-08 |
|
| Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster. | 2004-07-14 |
|
| Computer-assisted, high-performance liquid chromatography with mass spectrometric detection for the analysis of coumarins in Peucedanum palustre and Angelica archangelica. | 2004-06-19 |
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| The furanocoumarins in the roots of Heracleum sibiricum L. | 2004-03-10 |
|
| Cytotoxic activity of coumarins from the fruits of Cnidium monnieri on leukemia cell lines. | 2003-12 |
|
| LC determination of impurities in methoxsalen drug substance: isolation and identification of isopimpinellin as a major impurity by atmospheric pressure chemical ionization LC/MS and NMR. | 2003-11-24 |
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| Constituents of Peucedanum zenkeri seeds and their antimicrobial effects. | 2003-08 |
|
| [Studies on the coumarins in the root of Zanthoxylum dimorphophyllum]. | 2003-04 |
|
| Naturally occurring coumarins inhibit human cytochromes P450 and block benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene DNA adduct formation in MCF-7 cells. | 2003-03 |
|
| HPLC-NMR/HPLC-MS analysis of the bark extract of Stauranthus perforatus. | 2003-02-25 |
|
| A new dicoumarinyl ether and two rare furocoumarins from Ruta montana. | 2003-02 |
|
| Constituents of the fruits and leaves of Euodia daniellii. | 2002-12 |
|
| Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice. | 2002-10 |
|
| Effects of storage conditions on furocoumarin levels in intact, chopped, or homogenized parsnips. | 2002-04-24 |
|
| Amino acids in SRS1 and SRS6 are critical for furanocoumarin metabolism by CYP6B1v1, a cytochrome P450 monooxygenase. | 2002-04 |
|
| Simultaneous determination of furanocoumarins in infusions and decoctions from "Carapiá" (dorstenia species) by high-performance liquid chromatography. | 2002-03-13 |
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| Bullous phytophotodermatitis associated with high natural concentrations of furanocoumarins in limes. | 2002-03 |
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| Antipruritic effect of Cnidii Monnieri Fructus (fruits of Cnidium monnieri CUSSON). | 2002-02 |
|
| Role of cytochrome P450 1a1 and 1b1 in the metabolic activation of 7,12-dimethylbenz[a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation. | 2002-02 |
|
| Inhibition of itch-scratch response by fruits of Cnidium monnieri in mice. | 2001-09 |
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| Vasorelaxing effect of coumarins from Cnidium monnieri on rabbit corpus cavernosum. | 2001-04 |
|
| Oral administration of naturally occurring coumarins leads to altered phase I and II enzyme activities and reduced DNA adduct formation by polycyclic aromatic hydrocarbons in various tissues of SENCAR mice. | 2001-01 |
Patents
Sample Use Guides
RAW264.7 cells were seeded in 96-well plates and maintained in DMEM supplemented with 5% FBS, 100 U/ml penicillin, and 100 mg/ml streptomycin. After incubation at 37 °C for 24 h, compounds were added into the media and incubated for 4 h. Then LPS (1 mg/ml) was added and co-incubated for another 24 h. After that, the supernatant of the media was mixed with an equal volume of Griess reagent. Nitrite production was determined by measuring the optical density at 540 nm.
| Substance Class |
Chemical
Created
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| Record UNII |
20GCF755G6
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Validated (UNII)
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C45597
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28853
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Isopimpinellin
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C63673
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| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
| Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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