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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

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.

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
[Constituents of Liguliria vellerea (Franch.) Hand-Mazz].
2001 Dec
[Studies on chemical constituents of Stellera chamejasma L].
2001 Jul
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
Variation in coumarin 7-hydroxylase activity associated with genetic polymorphism of cytochrome P450 2A6 and the body status of iron stores in adult Thai males and females.
2002 Apr
[Studies on the chemical constituents from the roots and rhizomes of Gerbera piloselloides].
2002 Aug
Phenotypic polymorphism of CYP2A6 activity in a Chinese population.
2002 Aug
An in vivo pilot study characterizing the new CYP2A6*7, *8, and *10 alleles.
2002 Jan 11
Characterization by liquid chromatography-nuclear magnetic resonance spectroscopy and liquid chromatography-mass spectrometry of two coupled oxidative-conjugative metabolic pathways for 7-ethoxycoumarin in human liver microsomes treated with alamethicin.
2002 Mar
A novel ISFET-type biosensor based on P450 monooxygenases.
2002 Mar
[Prediction of eluotropic sequence of solutes in countercurrent chromatography].
2002 Nov
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
Single copy of variant CYP2A6 alleles does not confer susceptibility to liver dysfunction in patients treated with coumarin.
2003 Apr
Application of capillary electrophoresis with pH-mediated sample stacking to analysis of coumarin metabolites in microsomal incubations.
2003 Aug 8
'Open access' generic method for continuous determination of major human CYP450 probe substrates/metabolites and its application in drug metabolism studies.
2003 Dec
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
Potential functional foods in the traditional Maori diet.
2003 Feb-Mar
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
Protection of coumarins against linoleic acid hydroperoxide-induced cytotoxicity.
2003 Jan 6
Maintenance of liver functions in rat hepatocytes cultured as spheroids in a rotating wall vessel.
2003 Jan-Feb
Interactions of a series of novel spiropyranocoumarin derivatives with reactive oxygen species.
2003 Jul
A low background high-throughput screening (HTS) fluorescence assay for lipases and esterases using acyloxymethylethers of umbelliferone.
2003 Jul 7
Spectrofluorimetric analysis of 7-hydroxycoumarin binding to bovine phenol sulfotransferase.
2003 May 30
Modulation of mitogen-activated protein kinases by 6-nitro-7-hydroxycoumarin mediates apoptosis in renal carcinoma cells.
2003 Nov 28
The first fluorogenic assay for detecting a Baeyer-Villigerase activity in microbial cells.
2003 Oct 21
Coumarins from Peucedanum wulongense.
2003 Sep
Structural requirements of hydroxylated coumarins for in vitro anti-Helicobacter pylori activity.
2003 Sep-Oct
An active and water-soluble truncation mutant of the human UDP-glucuronosyltransferase 1A9.
2004 Apr
Functional characterization of single nucleotide polymorphisms with amino acid substitution in CYP1A2, CYP2A6, and CYP2B6 found in the Japanese population.
2004 Dec
Phase I and phase II metabolic activities are retained in liver slices from mouse, rat, dog, monkey and human after cryopreservation.
2004 Feb
[Isolation and structural identification of chemical constituents from Selaginella tamariscina (Beauv.) Spring].
2004 Jan
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
Validated assays for human cytochrome P450 activities.
2004 Jun
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
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
Determination of CC-5013, an analogue of thalidomide, in human plasma by liquid chromatography-mass spectrometry.
2004 Nov 25
Glucosylation of phenolic compounds by Pharbitis nil hairy roots: I. Glucosylation of coumarin and flavone derivatives.
2004 Oct
Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats.
2004 Oct 4
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
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
Analysis of substrate specificities and tissue expression of rat UDP-glucuronosyltransferases UGT1A7 and UGT1A8.
2005 Jan
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:03:59 UTC 2023
Edited
by admin
on Wed Jul 05 23:03:59 UTC 2023
Record UNII
60Z60NTL4G
Record Status Validated (UNII)
Record Version
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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 Wed Jul 05 23:03:59 UTC 2023 , Edited by admin on Wed Jul 05 23:03:59 UTC 2023
PRIMARY
NSC
19790
Created by admin on Wed Jul 05 23:03:59 UTC 2023 , Edited by admin on Wed Jul 05 23:03:59 UTC 2023
PRIMARY
MERCK INDEX
M11302
Created by admin on Wed Jul 05 23:03:59 UTC 2023 , Edited by admin on Wed Jul 05 23:03:59 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
202-240-3
Created by admin on Wed Jul 05 23:03:59 UTC 2023 , Edited by admin on Wed Jul 05 23:03:59 UTC 2023
PRIMARY
CAS
93-35-6
Created by admin on Wed Jul 05 23:03:59 UTC 2023 , Edited by admin on Wed Jul 05 23:03:59 UTC 2023
PRIMARY
WIKIPEDIA
UMBELLIFERONE
Created by admin on Wed Jul 05 23:03:59 UTC 2023 , Edited by admin on Wed Jul 05 23:03:59 UTC 2023
PRIMARY
FDA UNII
60Z60NTL4G
Created by admin on Wed Jul 05 23:03:59 UTC 2023 , Edited by admin on Wed Jul 05 23:03:59 UTC 2023
PRIMARY
PUBCHEM
5281426
Created by admin on Wed Jul 05 23:03:59 UTC 2023 , Edited by admin on Wed Jul 05 23:03:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID5052626
Created by admin on Wed Jul 05 23:03:59 UTC 2023 , Edited by admin on Wed Jul 05 23:03:59 UTC 2023
PRIMARY
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