U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin.
2005-08
Plant-derived anti-inflammatory compounds affect MIF tautomerase activity.
2005-05
Quantitative changes of secondary metabolites of Matricaria chamomilla by abiotic stress.
2005-04-09
Use of a cocktail of probe substrates for drug-metabolizing enzymes for the assessment of the metabolic capacity of hepatocyte preparations.
2005-04-02
Kinetic analysis of oxidation of coumarins by human cytochrome P450 2A6.
2005-04-01
Design and development of a fluorescent probe for monitoring hydrogen peroxide using photoinduced electron transfer.
2005-02-15
The influence of brain death on liver function.
2005-02
Lack of strain-related differences in drug metabolism and efflux transporter characteristics between CD-1 and athymic nude mice.
2005-02
Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture.
2005-01
Troxerutin protects the isolated perfused rat liver from a possible lipid peroxidation by coumarin.
2005-01
[Determination of scopoletin and umbelliferone contents in Saussurea medusa Maxim by high-performance liquid chromatography].
2005-01
Analysis of substrate specificities and tissue expression of rat UDP-glucuronosyltransferases UGT1A7 and UGT1A8.
2005-01
Functional characterization of single nucleotide polymorphisms with amino acid substitution in CYP1A2, CYP2A6, and CYP2B6 found in the Japanese population.
2004-12
Determination of CC-5013, an analogue of thalidomide, in human plasma by liquid chromatography-mass spectrometry.
2004-11-25
Evidence for concurrent effects of exposure to environmental cadmium and lead on hepatic CYP2A6 phenotype and renal function biomarkers in nonsmokers.
2004-11
A study of the role of cell cycle events mediating the action of coumarin derivatives in human malignant melanoma cells.
2004-10-08
Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats.
2004-10-04
Glucosylation of phenolic compounds by Pharbitis nil hairy roots: I. Glucosylation of coumarin and flavone derivatives.
2004-10
Novel squalene-hopene cyclase inhibitors derived from hydroxycoumarins and hydroxyacetophenones.
2004-10
Umbelliferone released from hairy root cultures of Pharbitis nil treated with copper sulfate and its subsequent glucosylation.
2004-09
Metabolic and structural viability of precision-cut rat lung slices in culture.
2004-08
Identification of Val117 and Arg372 as critical amino acid residues for the activity difference between human CYP2A6 and CYP2A13 in coumarin 7-hydroxylation.
2004-07-15
Effect of bisphenol A on drug metabolising enzymes in rat hepatic microsomes and precision-cut rat liver slices.
2004-07
Validated assays for human cytochrome P450 activities.
2004-06
Aldehyde detection by chromogenic/fluorogenic oxime bond fragmentation.
2004-05-21
Functional co-expression of xenobiotic metabolizing enzymes, rat cytochrome P450 1A1 and UDP-glucuronosyltransferase 1A6, in yeast microsomes.
2004-05-03
An active and water-soluble truncation mutant of the human UDP-glucuronosyltransferase 1A9.
2004-04
Effects of chronic exposure to low-level cadmium on renal tubular function and CYP2A6-mediated coumarin metabolism in healthy human subjects.
2004-03-21
Investigation of intracellular signalling events mediating the mechanism of action of 7-hydroxycoumarin and 6-nitro-7-hdroxycoumarin in human renal cells.
2004-03-08
Phase I and II enzyme characterization of two sources of HepG2 cell lines.
2004-03
Prediction of whole-body metabolic clearance of drugs through the combined use of slices from rat liver, lung, kidney, small intestine and colon.
2004-03
[Isolation and structure identification of the chemical constituents from pine needles of Pinus massoniana Lamb].
2004-03
Apoptosis and cell cycle disturbances induced by coumarin and 7-hydroxycoumarin on human lung carcinoma cell lines.
2004-03
Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru.
2004-03
Phase I and phase II metabolic activities are retained in liver slices from mouse, rat, dog, monkey and human after cryopreservation.
2004-02
Absolute stereochemistry of dihydrofuroangelicins bearing C-8 substituted double bonds: a combined chemical/exciton chirality protocol.
2004-01-07
[Isolation and structural identification of chemical constituents from Selaginella tamariscina (Beauv.) Spring].
2004-01
Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer.
2004
'Open access' generic method for continuous determination of major human CYP450 probe substrates/metabolites and its application in drug metabolism studies.
2003-12
Study of inhibition of CYP2A6 by some drugs derived from quinoline.
2003-12
Modulation of mitogen-activated protein kinases by 6-nitro-7-hydroxycoumarin mediates apoptosis in renal carcinoma cells.
2003-11-28
Structural requirements of hydroxylated coumarins for in vitro anti-Helicobacter pylori activity.
2003-11-06
The first fluorogenic assay for detecting a Baeyer-Villigerase activity in microbial cells.
2003-10-21
Coumarins from Peucedanum wulongense.
2003-09
Application of capillary electrophoresis with pH-mediated sample stacking to analysis of coumarin metabolites in microsomal incubations.
2003-08-08
Maintenance of liver functions in rat hepatocytes cultured as spheroids in a rotating wall vessel.
2003-08-02
A low background high-throughput screening (HTS) fluorescence assay for lipases and esterases using acyloxymethylethers of umbelliferone.
2003-07-07
Interactions of a series of novel spiropyranocoumarin derivatives with reactive oxygen species.
2003-07
[Studies on the chemical constituents from the roots and rhizomes of Gerbera piloselloides].
2002-08
A new technique for preparing precision-cut slices from small intestine and colon for drug biotransformation studies.
2001-12-24
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 Mon Mar 31 18:01:43 GMT 2025
Edited
by admin
on Mon Mar 31 18:01:43 GMT 2025
Record UNII
60Z60NTL4G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-19790
Preferred Name English
UMBELLIFERONE
MI  
Common Name English
SKIMMETIN
Common Name English
Umbelliferone [WHO-DD]
Common Name English
SKIMMETINE
Common Name English
HYDRANGIN
Common Name 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 Mon Mar 31 18:01:43 GMT 2025 , Edited by admin on Mon Mar 31 18:01:43 GMT 2025
PRIMARY
NSC
19790
Created by admin on Mon Mar 31 18:01:43 GMT 2025 , Edited by admin on Mon Mar 31 18:01:43 GMT 2025
PRIMARY
MERCK INDEX
m11302
Created by admin on Mon Mar 31 18:01:43 GMT 2025 , Edited by admin on Mon Mar 31 18:01:43 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
202-240-3
Created by admin on Mon Mar 31 18:01:43 GMT 2025 , Edited by admin on Mon Mar 31 18:01:43 GMT 2025
PRIMARY
CAS
93-35-6
Created by admin on Mon Mar 31 18:01:43 GMT 2025 , Edited by admin on Mon Mar 31 18:01:43 GMT 2025
PRIMARY
WIKIPEDIA
UMBELLIFERONE
Created by admin on Mon Mar 31 18:01:43 GMT 2025 , Edited by admin on Mon Mar 31 18:01:43 GMT 2025
PRIMARY
FDA UNII
60Z60NTL4G
Created by admin on Mon Mar 31 18:01:43 GMT 2025 , Edited by admin on Mon Mar 31 18:01:43 GMT 2025
PRIMARY
PUBCHEM
5281426
Created by admin on Mon Mar 31 18:01:43 GMT 2025 , Edited by admin on Mon Mar 31 18:01:43 GMT 2025
PRIMARY
EPA CompTox
DTXSID5052626
Created by admin on Mon Mar 31 18:01:43 GMT 2025 , Edited by admin on Mon Mar 31 18:01:43 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
PARENT -> METABOLITE