Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H6O3 |
Molecular Weight | 162.1421 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC2=C(C=CC(=O)O2)C=C1
InChI
InChIKey=ORHBXUUXSCNDEV-UHFFFAOYSA-N
InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
Molecular Formula | C9H6O3 |
Molecular Weight | 162.1421 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Umbelliferone is a natural product of the coumarin family which can be found in many different plant species. It absorbs ultraviolet light strongly at several wavelengths and is used in sunscreens. It has also been reported to have antioxidant, anti-inflammatory, and anti-nocioceptive properties.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0007050 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25997538 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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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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[Constituents of Liguliria vellerea (Franch.) Hand-Mazz]. | 2001 Dec |
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[Studies on chemical constituents of Stellera chamejasma L]. | 2001 Jul |
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[Studies on the chemical constituents from the roots and rhizomes of Gerbera piloselloides]. | 2002 Aug |
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[Prediction of eluotropic sequence of solutes in countercurrent chromatography]. | 2002 Nov |
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Single copy of variant CYP2A6 alleles does not confer susceptibility to liver dysfunction in patients treated with coumarin. | 2003 Apr |
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Application of capillary electrophoresis with pH-mediated sample stacking to analysis of coumarin metabolites in microsomal incubations. | 2003 Aug 8 |
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'Open access' generic method for continuous determination of major human CYP450 probe substrates/metabolites and its application in drug metabolism studies. | 2003 Dec |
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Study of inhibition of CYP2A6 by some drugs derived from quinoline. | 2003 Dec |
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Fluorogenic stereochemical probes for transaldolases. | 2003 Feb 17 |
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Maintenance of liver functions in rat hepatocytes cultured as spheroids in a rotating wall vessel. | 2003 Jan-Feb |
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A low background high-throughput screening (HTS) fluorescence assay for lipases and esterases using acyloxymethylethers of umbelliferone. | 2003 Jul 7 |
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Spectrofluorimetric analysis of 7-hydroxycoumarin binding to bovine phenol sulfotransferase. | 2003 May 30 |
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Modulation of mitogen-activated protein kinases by 6-nitro-7-hydroxycoumarin mediates apoptosis in renal carcinoma cells. | 2003 Nov 28 |
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The first fluorogenic assay for detecting a Baeyer-Villigerase activity in microbial cells. | 2003 Oct 21 |
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Coumarins from Peucedanum wulongense. | 2003 Sep |
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Structural requirements of hydroxylated coumarins for in vitro anti-Helicobacter pylori activity. | 2003 Sep-Oct |
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Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. | 2004 |
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An active and water-soluble truncation mutant of the human UDP-glucuronosyltransferase 1A9. | 2004 Apr |
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Functional characterization of single nucleotide polymorphisms with amino acid substitution in CYP1A2, CYP2A6, and CYP2B6 found in the Japanese population. | 2004 Dec |
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Phase I and phase II metabolic activities are retained in liver slices from mouse, rat, dog, monkey and human after cryopreservation. | 2004 Feb |
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[Isolation and structural identification of chemical constituents from Selaginella tamariscina (Beauv.) Spring]. | 2004 Jan |
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Absolute stereochemistry of dihydrofuroangelicins bearing C-8 substituted double bonds: a combined chemical/exciton chirality protocol. | 2004 Jan 7 |
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Effect of bisphenol A on drug metabolising enzymes in rat hepatic microsomes and precision-cut rat liver slices. | 2004 Jul |
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Identification of Val117 and Arg372 as critical amino acid residues for the activity difference between human CYP2A6 and CYP2A13 in coumarin 7-hydroxylation. | 2004 Jul 15 |
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Quantitative changes of secondary metabolites of Matricaria chamomilla by abiotic stress. | 2004 Jul-Aug |
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Validated assays for human cytochrome P450 activities. | 2004 Jun |
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Prediction of whole-body metabolic clearance of drugs through the combined use of slices from rat liver, lung, kidney, small intestine and colon. | 2004 Mar |
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[Isolation and structure identification of the chemical constituents from pine needles of Pinus massoniana Lamb]. | 2004 Mar |
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Apoptosis and cell cycle disturbances induced by coumarin and 7-hydroxycoumarin on human lung carcinoma cell lines. | 2004 Mar |
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Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru. | 2004 Mar |
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Effects of chronic exposure to low-level cadmium on renal tubular function and CYP2A6-mediated coumarin metabolism in healthy human subjects. | 2004 Mar 21 |
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Investigation of intracellular signalling events mediating the mechanism of action of 7-hydroxycoumarin and 6-nitro-7-hdroxycoumarin in human renal cells. | 2004 Mar 8 |
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Aldehyde detection by chromogenic/fluorogenic oxime bond fragmentation. | 2004 May 21 |
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Evidence for concurrent effects of exposure to environmental cadmium and lead on hepatic CYP2A6 phenotype and renal function biomarkers in nonsmokers. | 2004 Nov |
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Determination of CC-5013, an analogue of thalidomide, in human plasma by liquid chromatography-mass spectrometry. | 2004 Nov 25 |
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Use of a cocktail of probe substrates for drug-metabolizing enzymes for the assessment of the metabolic capacity of hepatocyte preparations. | 2004 Nov-Dec |
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Glucosylation of phenolic compounds by Pharbitis nil hairy roots: I. Glucosylation of coumarin and flavone derivatives. | 2004 Oct |
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Novel squalene-hopene cyclase inhibitors derived from hydroxycoumarins and hydroxyacetophenones. | 2004 Oct |
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A study of the role of cell cycle events mediating the action of coumarin derivatives in human malignant melanoma cells. | 2004 Oct 8 |
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Umbelliferone released from hairy root cultures of Pharbitis nil treated with copper sulfate and its subsequent glucosylation. | 2004 Sep |
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Kinetic analysis of oxidation of coumarins by human cytochrome P450 2A6. | 2005 Apr 1 |
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Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin. | 2005 Aug |
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Lack of strain-related differences in drug metabolism and efflux transporter characteristics between CD-1 and athymic nude mice. | 2005 Feb |
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Design and development of a fluorescent probe for monitoring hydrogen peroxide using photoinduced electron transfer. | 2005 Feb 15 |
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Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture. | 2005 Jan |
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Troxerutin protects the isolated perfused rat liver from a possible lipid peroxidation by coumarin. | 2005 Jan |
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[Determination of scopoletin and umbelliferone contents in Saussurea medusa Maxim by high-performance liquid chromatography]. | 2005 Jan |
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Analysis of substrate specificities and tissue expression of rat UDP-glucuronosyltransferases UGT1A7 and UGT1A8. | 2005 Jan |
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A new technique for preparing precision-cut slices from small intestine and colon for drug biotransformation studies. | 2005 Jan-Feb |
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Plant-derived anti-inflammatory compounds affect MIF tautomerase activity. | 2005 May |
Patents
Sample Use Guides
Male Swiss mice were pretreated with Umbelliferone (1.0 and 2.5 mg/kg orally). One hour later they were injected with acetic acid 0.6%. Then after 10 minutes the number of writhings was recorded for 20 min. Antinociceptive activity was evaluated in terms of the percentage of contraction inhibitions. Umbelliferone showed 74% inhibition of writhing contractions and was not reversed by the opioid antagonist naloxone.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28586740
Human oral carcinoma cells (KB cells) were cultured in Dulbecco's Modified Eagle Medium supplemented with 10 % heat-inactivated fetal bovine serum, 100 U/mL of penicillin and 100 micro-g/mL of streptomycin at 37 deg-C in a humidified 5% CO2 atmosphere. KB cells were seeded in 96 well plates at a concentration of 6000 cells per plate. After 24 hours of incubation, the medium was replaced with media dosed with umbelliferone at various concentrations of 50, 100, 150, 200, 250, 300, 400 and 450mM/well. After 48 hours the drug-containing medium was replaced with 100 microL of medium containing MTT in order to determine cell viability. Cell viability was significantly decreased to 80, 72, 63 and 44% when cells were exposed to umbelliferone at concentrations of 50, 100, 150 and 200mM/ml respectively.
Substance Class |
Chemical
Created
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admin
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Edited
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Record UNII |
60Z60NTL4G
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Record Status |
Validated (UNII)
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Record Version |
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UMBELLIFERONE
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