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Details

Stereochemistry ACHIRAL
Molecular Formula C9H6O3
Molecular Weight 162.1425
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UMBELLIFERONE

SMILES

c1cc(cc2c1ccc(=O)o2)O

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 162.1425
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
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
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
[Studies on chemical constituents of Stellera chamejasma L].
2001 Jul
Consumption of watercress fails to alter coumarin metabolism in humans.
2001 Jun
Expression of CYP2A6 in tumor cells augments cellular sensitivity to tegafur.
2001 May
[Nonpolar components of the leaves of Philadelphus coronarius L].
2001 Nov
Crystal structure of gamma-chymotrypsin in complex with 7-hydroxycoumarin.
2001 Nov 30
Study of the in vitro cytotoxic potential of natural and synthetic coumarin derivatives using human normal and neoplastic skin cell lines.
2001 Oct
Tissue slices revisited: evaluation and development of a short-term incubation for integrated drug metabolism.
2001 Oct
A novel class of inhibitors for steroid 5alpha-reductase: synthesis and evaluation of umbelliferone derivatives.
2001 Sep 3
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
[Studies on the chemical constituents from the roots and rhizomes of Gerbera piloselloides].
2002 Aug
Inhibitory effects of phenylpropanoid metabolites on copper-induced protein oxidative modification of mice brain homogenate, in vitro.
2002 Feb
An in vivo pilot study characterizing the new CYP2A6*7, *8, and *10 alleles.
2002 Jan 11
[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
Single copy of variant CYP2A6 alleles does not confer susceptibility to liver dysfunction in patients treated with coumarin.
2003 Apr
Fluorogenic stereochemical probes for transaldolases.
2003 Feb 17
Potential functional foods in the traditional Maori diet.
2003 Feb-Mar
Protection of coumarins against linoleic acid hydroperoxide-induced cytotoxicity.
2003 Jan 6
Interactions of a series of novel spiropyranocoumarin derivatives with reactive oxygen species.
2003 Jul
Modulation of mitogen-activated protein kinases by 6-nitro-7-hydroxycoumarin mediates apoptosis in renal carcinoma cells.
2003 Nov 28
[Isolation and structural identification of chemical constituents from Selaginella tamariscina (Beauv.) Spring].
2004 Jan
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
Validated assays for human cytochrome P450 activities.
2004 Jun
Aldehyde detection by chromogenic/fluorogenic oxime bond fragmentation.
2004 May 21
Functional co-expression of xenobiotic metabolizing enzymes, rat cytochrome P450 1A1 and UDP-glucuronosyltransferase 1A6, in yeast microsomes.
2004 May 3
Determination of CC-5013, an analogue of thalidomide, in human plasma by liquid chromatography-mass spectrometry.
2004 Nov 25
Use of a cocktail of probe substrates for drug-metabolizing enzymes for the assessment of the metabolic capacity of hepatocyte preparations.
2004 Nov-Dec
Novel squalene-hopene cyclase inhibitors derived from hydroxycoumarins and hydroxyacetophenones.
2004 Oct
A study of the role of cell cycle events mediating the action of coumarin derivatives in human malignant melanoma cells.
2004 Oct 8
Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin.
2005 Aug
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
Analysis of substrate specificities and tissue expression of rat UDP-glucuronosyltransferases UGT1A7 and UGT1A8.
2005 Jan
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 Sat Jun 26 06:26:44 UTC 2021
Edited
by admin
on Sat Jun 26 06:26:44 UTC 2021
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
MERCK INDEX
M11302
Created by admin on Sat Jun 26 06:26:45 UTC 2021 , Edited by admin on Sat Jun 26 06:26:45 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
202-240-3
Created by admin on Sat Jun 26 06:26:45 UTC 2021 , Edited by admin on Sat Jun 26 06:26:45 UTC 2021
PRIMARY
CAS
93-35-6
Created by admin on Sat Jun 26 06:26:45 UTC 2021 , Edited by admin on Sat Jun 26 06:26:45 UTC 2021
PRIMARY
WIKIPEDIA
UMBELLIFERONE
Created by admin on Sat Jun 26 06:26:45 UTC 2021 , Edited by admin on Sat Jun 26 06:26:45 UTC 2021
PRIMARY
FDA UNII
60Z60NTL4G
Created by admin on Sat Jun 26 06:26:45 UTC 2021 , Edited by admin on Sat Jun 26 06:26:45 UTC 2021
PRIMARY
PUBCHEM
5281426
Created by admin on Sat Jun 26 06:26:45 UTC 2021 , Edited by admin on Sat Jun 26 06:26:45 UTC 2021
PRIMARY
EPA CompTox
93-35-6
Created by admin on Sat Jun 26 06:26:45 UTC 2021 , Edited by admin on Sat Jun 26 06:26:45 UTC 2021
PRIMARY
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