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
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
A new bicoumarin from Stellera chamaejasme L.
2001
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
High-throughput cytochrome P450 (CYP) inhibition screening via a cassette probe-dosing strategy. VI. Simultaneous evaluation of inhibition potential of drugs on human hepatic isozymes CYP2A6, 3A4, 2C9, 2D6 and 2E1.
2001
Cellular distribution and handling of liver-targeting preparations in human livers studied by a liver lobe perfusion.
2001 Apr
[Constituents of Liguliria vellerea (Franch.) Hand-Mazz].
2001 Dec
Induction of 4-hydroxycinnamate decarboxylase in Klebsiella oxytoca cells exposed to substrates and non-substrate 4-hydroxycinnamate analogs.
2001 Dec
The in vivo dermal absorption and metabolism of [4-14C] coumarin by rats and by human volunteers under simulated conditions of use in fragrances.
2001 Feb
Excited-state dipole moments of some hydroxycoumarin dyes using an efficient solvatochromic method based on the solvent polarity parameter, EN(T).
2001 Jan
[Sensitization and crossreaction of simple coumarins].
2001 Jan
[Studies on chemical constituents of Stellera chamejasma L].
2001 Jul
Consumption of watercress fails to alter coumarin metabolism in humans.
2001 Jun
Cellular distribution and handling of liver-targeting preparations in human livers studied by a liver lobe perfusion.
2001 Jun
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.
2001 Mar
[Nonpolar components of the leaves of Philadelphus coronarius L].
2001 Nov
Crystal structure of gamma-chymotrypsin in complex with 7-hydroxycoumarin.
2001 Nov 30
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
A novel class of inhibitors for steroid 5alpha-reductase: synthesis and evaluation of umbelliferone derivatives.
2001 Sep 3
Superoxide organic chemistry within the liposomal bilayer, part II: a correlation between location and chemistry.
2002 Apr 1
[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
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
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
Comparative metabolism and kinetics of coumarin in mice and rats.
2003 Feb
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
Spectrofluorimetric analysis of 7-hydroxycoumarin binding to bovine phenol sulfotransferase.
2003 May 30
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
Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer.
2004
An active and water-soluble truncation mutant of the human UDP-glucuronosyltransferase 1A9.
2004 Apr
Absolute stereochemistry of dihydrofuroangelicins bearing C-8 substituted double bonds: a combined chemical/exciton chirality protocol.
2004 Jan 7
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
Apoptosis and cell cycle disturbances induced by coumarin and 7-hydroxycoumarin on human lung carcinoma cell lines.
2004 Mar
Effects of chronic exposure to low-level cadmium on renal tubular function and CYP2A6-mediated coumarin metabolism in healthy human subjects.
2004 Mar 21
Functional co-expression of xenobiotic metabolizing enzymes, rat cytochrome P450 1A1 and UDP-glucuronosyltransferase 1A6, in yeast microsomes.
2004 May 3
Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats.
2004 Oct 4
A study of the role of cell cycle events mediating the action of coumarin derivatives in human malignant melanoma cells.
2004 Oct 8
Kinetic analysis of oxidation of coumarins by human cytochrome P450 2A6.
2005 Apr 1
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:34:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:34:39 GMT 2023
Record UNII
60Z60NTL4G
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
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