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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
Structure of UMBELLIFERONE

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

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds.
1999 Aug 26
Mono- and sesquiterpenes and antifungal constituents from Artemisia species.
1999 Feb
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor.
2000 Jun 20
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
Determination of coumarin metabolism in Turkish population.
2001 Apr
Induction of 4-hydroxycinnamate decarboxylase in Klebsiella oxytoca cells exposed to substrates and non-substrate 4-hydroxycinnamate analogs.
2001 Dec
[Studies on chemical constituents of Stellera chamejasma L].
2001 Jul
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.
2001 Mar
The role of cytochrome 2B1 substrate recognition site residues 115, 294, 297, 298, and 362 in the oxidation of steroids and 7-alkoxycoumarins.
2001 Oct 1
Some coumarins and triphenylethene derivatives as inhibitors of human testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3): further studies with tamoxifen on the rat testes microsomal enzyme.
2002 Apr
A novel ISFET-type biosensor based on P450 monooxygenases.
2002 Mar
Drug-metabolizing activity of human and rat liver, lung, kidney and intestine slices.
2002 May
Characterization of testosterone metabolism and 7-hydroxycoumarin conjugation by rat and human liver slices after storage in liquid nitrogen for 1 h up to 6 months.
2002 Nov
Monolithic silica rod liquid chromatography with ultraviolet or fluorescence detection for metabolite analysis of cytochrome P450 marker reactions.
2002 Nov 25
Study of inhibition of CYP2A6 by some drugs derived from quinoline.
2003 Dec
Comparative metabolism and kinetics of coumarin in mice and rats.
2003 Feb
Chemical constituents from the Hydrangea chinensis.
2003 Jan
CYP2A13-catalysed coumarin metabolism: comparison with CYP2A5 and CYP2A6.
2003 Jan
Is neuroprotective efficacy of nNOS inhibitor 7-NI dependent on ischemic intracellular pH?
2003 Jan
Modulation of mitogen-activated protein kinases by 6-nitro-7-hydroxycoumarin mediates apoptosis in renal carcinoma cells.
2003 Nov 28
Structural requirements of hydroxylated coumarins for in vitro anti-Helicobacter pylori activity.
2003 Sep-Oct
Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer.
2004
Absolute stereochemistry of dihydrofuroangelicins bearing C-8 substituted double bonds: a combined chemical/exciton chirality protocol.
2004 Jan 7
Effect of bisphenol A on drug metabolising enzymes in rat hepatic microsomes and precision-cut rat liver slices.
2004 Jul
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
Quantitative changes of secondary metabolites of Matricaria chamomilla by abiotic stress.
2004 Jul-Aug
Phase I and II enzyme characterization of two sources of HepG2 cell lines.
2004 Mar
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
Evidence for concurrent effects of exposure to environmental cadmium and lead on hepatic CYP2A6 phenotype and renal function biomarkers in nonsmokers.
2004 Nov
Use of a cocktail of probe substrates for drug-metabolizing enzymes for the assessment of the metabolic capacity of hepatocyte preparations.
2004 Nov-Dec
Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin.
2005 Aug
The influence of brain death on liver function.
2005 Feb
Lack of strain-related differences in drug metabolism and efflux transporter characteristics between CD-1 and athymic nude mice.
2005 Feb
Design and development of a fluorescent probe for monitoring hydrogen peroxide using photoinduced electron transfer.
2005 Feb 15
Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture.
2005 Jan
A new technique for preparing precision-cut slices from small intestine and colon for drug biotransformation studies.
2005 Jan-Feb
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
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.
Name Type Language
UMBELLIFERONE
MI  
Common Name English
SKIMMETIN
Common Name English
Umbelliferone [WHO-DD]
Common Name English
SKIMMETINE
Common Name English
HYDRANGIN
Common Name English
NSC-19790
Code English
UMBELLIFERONE [MI]
Common Name English
2H-1-BENZOPYRAN-2-ONE, 7-HYDROXY-
Systematic Name English
7 OH COUMARIN
Common Name English
7-HYDROXYCOUMARIN
Systematic Name English
Code System Code Type Description
CHEBI
27510
Created by admin on Fri Dec 15 15:34:39 GMT 2023 , Edited by admin on Fri Dec 15 15:34:39 GMT 2023
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NSC
19790
Created by admin on Fri Dec 15 15:34:39 GMT 2023 , Edited by admin on Fri Dec 15 15:34:39 GMT 2023
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MERCK INDEX
m11302
Created by admin on Fri Dec 15 15:34:39 GMT 2023 , Edited by admin on Fri Dec 15 15:34:39 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
202-240-3
Created by admin on Fri Dec 15 15:34:39 GMT 2023 , Edited by admin on Fri Dec 15 15:34:39 GMT 2023
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CAS
93-35-6
Created by admin on Fri Dec 15 15:34:39 GMT 2023 , Edited by admin on Fri Dec 15 15:34:39 GMT 2023
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WIKIPEDIA
UMBELLIFERONE
Created by admin on Fri Dec 15 15:34:39 GMT 2023 , Edited by admin on Fri Dec 15 15:34:39 GMT 2023
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FDA UNII
60Z60NTL4G
Created by admin on Fri Dec 15 15:34:39 GMT 2023 , Edited by admin on Fri Dec 15 15:34:39 GMT 2023
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PUBCHEM
5281426
Created by admin on Fri Dec 15 15:34:39 GMT 2023 , Edited by admin on Fri Dec 15 15:34:39 GMT 2023
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EPA CompTox
DTXSID5052626
Created by admin on Fri Dec 15 15:34:39 GMT 2023 , Edited by admin on Fri Dec 15 15:34:39 GMT 2023
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