umbelliprenin profile

umbelliprenin: RN given refers to cpd with unspecified isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	1781413
CHEMBL ID	156127
CHEBI ID	172086
SCHEMBL ID	18265478
MeSH ID	M0044841

Synonym
CHEBI:172086
532-16-1
7-[(2e,6e)-3,7,11-trimethyldodeca-2,6,10-trienoxy]chromen-2-one
umbelliprenin
bdbm50143435
7-((2e,6e)-3,7,11-trimethyl-dodeca-2,6,10-trienyloxy)-chromen-2-one
MLS002472936
smr001397045
CHEMBL156127 ,
NCGC00247456-01
30413-87-7
coumarin, 7-((3,7,22-trimethyl-2,6,10-dodecatrienyl)oxy)-
HMS2205K17
(e,e)-7-((3,7,11-trimethyl-2,6,10-dodecatrienyl)oxy)-2h-1-benzopyran-2-one
angelin
msd8n8a1lq ,
23838-17-7
unii-msd8n8a1lq
7-farnesyloxycoumarin
2h-1-benzopyran-2-one, 7-(((2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)oxy)-
umbelliprenine
SCHEMBL18265478
7-(((2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)-2h-chromen-2-one
Q27284214
XU163805
DTXSID901317603
7-[[(2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrienyl]oxy]-2h-1-benzopyran-2-one
AKOS040763680
2h-1-benzopyran-2-one, 7-[(3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)oxy]-

Excerpt	Reference	Relevance
"Umbelliprenin is a secondary plant metabolite that displays promising chemopreventive, anti-inflammatory, and antigenotoxic properties. "	( Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species. Bize, C; de Medina, P; Epifano, F; Fiorito, S; Genovese, S; Rives, A; Taddeo, VA, 2017)	2.15
"Umbelliprenin is a sesquiterpene coumarin isolated from Artemisia absinthium L. "	( Umbelliprenin induces autophagy and apoptosis while inhibits cancer cell stemness in pancreatic cancer cells. Huang, X; Liu, Y; Wang, H; Wang, Y; Xia, G; Xu, T, 2023)	3.8
"Umbelliprenin (UMB) is a prenylated coumarin that acts as an in vitro antioxidant and inhibits lipoxygenase managing the inflammation pathways, while in vivo it exerts anti-inflammatory activities."	( Umbelliprenin relieves paclitaxel-induced neuropathy. Bagheri, G; Hashemzaei, M; Jahantigh, H; Mohammadzehi Kenar, S; Rezaee, R; Setoodeh Nezhad, S; Shahraki, J; Tsarouhas, K, 2020)	3.44
"Umbelliprenin is a member of the 7-prenyloxycoumarins with potential therapeutic properties such as cytotoxic effects on various cancer cells. "	( Umbelliprenin induced production of IFN-γ and TNF-α, and reduced IL-10, IL-4, Foxp3 and TGF-β in a mouse model of lung cancer. Ghaderi, A; Hosseinzadeh, M; Khaghanzadeh, N; Mojtahedi, Z; Ramezani, M; Samiei, A, 2014)	3.29
"Umbelliprenin is a prenylated compound, which belongs to the class of sesquiterpene coumarins. "	( Cancer chemopreventive activity of the prenylated coumarin, umbelliprenin, in vivo. Iranshahi, M; Konoshima, T; Sahebkar, A; Takasaki, M; Tokuda, H, 2009)	2.04

Excerpt	Reference	Relevance
"Umbelliprenin (UMB) has shown various pharmacological properties in vitro. "	( Umbelliprenin shows antitumor, antiangiogenesis, antimetastatic, anti-inflammatory, and immunostimulatory activities in 4T1 tumor-bearing Balb/c mice. Amani, D; Bazi, A; Jamshidi, H; Khalilnezhad, A; Muhammadnejad, A; Rashidi, M; Ziai, SA, 2018)	3.37

Excerpt	Reference	Relevance
" The aim of the current research was to compare toxic effects of GBA, AUR, and UMB on human lymphoma cells in normoxia and hypoxia."	( Comparing toxicity of galbanic acid, auraptene and umbelliprenin on adult T-cell leukaemia-lymphoma in normoxia and hypoxia. Goudarzi, S; Kahrizi, D; Keramati, MR; Mahdifar, M; Rassouli, FB, 2022)	0.97

Class	Description
terpene lactone
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASE	Homo sapiens (human)	Potency	44.6684	0.0040	23.8416	100.0000	AID485290
Chain A, JmjC domain-containing histone demethylation protein 3A	Homo sapiens (human)	Potency	56.2341	0.6310	35.7641	100.0000	AID504339
acid sphingomyelinase	Homo sapiens (human)	Potency	31.6228	14.1254	24.0613	39.8107	AID504937
thioredoxin reductase	Rattus norvegicus (Norway rat)	Potency	63.0957	0.1000	20.8793	79.4328	AID588456
TDP1 protein	Homo sapiens (human)	Potency	23.7246	0.0008	11.3822	44.6684	AID686978; AID686979
PINK1	Homo sapiens (human)	Potency	50.1187	2.8184	18.8959	44.6684	AID624263
Parkin	Homo sapiens (human)	Potency	50.1187	0.8199	14.8306	44.6684	AID624263
chromobox protein homolog 1	Homo sapiens (human)	Potency	50.1187	0.0060	26.1688	89.1251	AID540317
importin subunit beta-1 isoform 1	Homo sapiens (human)	Potency	112.2020	5.8048	36.1306	65.1308	AID540263
flap endonuclease 1	Homo sapiens (human)	Potency	79.4328	0.1337	25.4129	89.1251	AID588795
snurportin-1	Homo sapiens (human)	Potency	112.2020	5.8048	36.1306	65.1308	AID540263
DNA polymerase iota isoform a (long)	Homo sapiens (human)	Potency	79.4328	0.0501	27.0736	89.1251	AID588590
geminin	Homo sapiens (human)	Potency	0.4611	0.0046	11.3741	33.4983	AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)	IC50 (µMol)	16.7000	0.0400	2.0998	10.0000	AID683124
Squalene--hopene cyclase	Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446	IC50 (µMol)	70.0000	0.0600	3.5300	7.0000	AID204671
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Melatonin receptor type 1A	Homo sapiens (human)	KiH	0.0016	0.0016	0.0016	0.0016	AID1347657
Melatonin receptor type 1A	Homo sapiens (human)	KiL	0.0033	0.0033	0.0033	0.0033	AID1347657
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
ossification	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
negative regulation of adaptive immune response	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
lipid metabolic process	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
phosphatidylethanolamine biosynthetic process	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
inflammatory response	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
positive regulation of cell-substrate adhesion	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
arachidonic acid metabolic process	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
lipoxygenase pathway	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
fatty acid oxidation	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
bone mineralization	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
positive regulation of actin filament polymerization	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
response to endoplasmic reticulum stress	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
regulation of peroxisome proliferator activated receptor signaling pathway	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
cellular response to interleukin-13	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
wound healing	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
apoptotic cell clearance	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
linoleic acid metabolic process	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
regulation of inflammatory response	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
hepoxilin biosynthetic process	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascade	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
cellular response to calcium ion	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
regulation of engulfment of apoptotic cell	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
lipoxin A4 biosynthetic process	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
lipid oxidation	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	Melatonin receptor type 1A	Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway	Melatonin receptor type 1A	Homo sapiens (human)
mating behavior	Melatonin receptor type 1A	Homo sapiens (human)
circadian rhythm	Melatonin receptor type 1A	Homo sapiens (human)
G protein-coupled receptor signaling pathway	Melatonin receptor type 1A	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
arachidonate 12(S)-lipoxygenase activity	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
iron ion binding	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
protein binding	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
phosphatidylinositol-4,5-bisphosphate binding	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
linoleate 13S-lipoxygenase activity	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
arachidonate 15-lipoxygenase activity	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
protein binding	Melatonin receptor type 1A	Homo sapiens (human)
melatonin receptor activity	Melatonin receptor type 1A	Homo sapiens (human)
hormone binding	Melatonin receptor type 1A	Homo sapiens (human)
organic cyclic compound binding	Melatonin receptor type 1A	Homo sapiens (human)
G protein-coupled receptor activity	Melatonin receptor type 1A	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
lipid droplet	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
cytosol	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
plasma membrane	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
cytoplasmic side of plasma membrane	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
membrane	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
plasma membrane	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
cytosol	Polyunsaturated fatty acid lipoxygenase ALOX15	Homo sapiens (human)
plasma membrane	Melatonin receptor type 1A	Homo sapiens (human)
receptor complex	Melatonin receptor type 1A	Homo sapiens (human)
plasma membrane	Melatonin receptor type 1A	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (95)

Assay ID	Title	Year	Journal	Article
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1359349	Decrease in TRP1 mRNA expression in mouse Melan-a cells at 40 uM after 24 hrs by SYBR green dye based qRT-PCR analysis relative to control	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501422	Photochemical stability of the compound assessed as compound degradation under sunlight using solid samples measured up to 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501419	Stability of the compound assessed as compound degradation in 0.1 M NaOH solution at 60 degC in EtOH solution after 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501439	Photostability of the compound assessed as parent compound remaining under sunlight exposed for 3 days in EtOH solution measured by TLC method	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501437	Photostability of the compound assessed as parent compound remaining under sunlight exposed for 6 days in EtOH solution measured in presence of UV-B filter octinoxate by TLC method	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501428	Drug metabolism assessed as P2 metabolite formation under sunlight in EtOH solution after 4 days by TLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347667	Inhibition of cell migration in mouse mammary carcinoma cell at 100 uM after 24 hrs by inverted fluorescence microscopy based scratch assay relative to control	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501433	Photostability of the compound assessed as parent compound remaining under sunlight exposed for 3 days in EtOH solution measured in presence of UV-B filter octinoxate by TLC method	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1163511	Cytotoxicity against human PANC1 cells under nutrient-rich condition after 24 hrs by WST8 dye based assay	2014	Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19	Synthesis and biological evaluation of isoprenylated coumarins as potential anti-pancreatic cancer agents.
AID1501434	Photostability of the compound assessed as parent compound remaining under sunlight exposed for 3 days in EtOH solution measured in presence of antioxidant DL-alpha-tocopherol acetate by TLC method	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347662	Antiproliferative activity against human MCF7 cells at 1 nM to 100 uM after 24 hrs by MTT assay relative to control	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1347666	Inhibition of cell migration in human MCF7 cells at 100 uM after 24 hrs by inverted fluorescence microscopy based scratch assay relative to control	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501423	Photochemical stability of the compound assessed as compound degradation under 254 nm UV-light exposure using solid samples measured up to 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359353	Effect on TRP2 expression in mouse Melan-a cells at 40 uM after 72 hrs by western blot analysis (Rvb = 1 No_unit)	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501429	Drug metabolism assessed as (6aR,6bS,12bS,12cR)-3,10-Bis-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyloxy)-6a,6b,12b,12c-tetrahydro-5,8-dioxa-dibenzo[a,i]biphenylene-6,7-dione formation under sunlight in EtOH solution after 6 days by 1H-NMR analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359363	Antimelanogenic activity in mouse Melan-a cells assessed as inhibition of UV irradiation-stimulated melanin synthesis at 40 uM measured after 72 hrs	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID683122	Inhibition of soybean 15-lipoxygenase by MBTH-DMAB method	2012	European journal of medicinal chemistry, Nov, Volume: 57	Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors.
AID1501413	Thermal stability of the compound assessed as compound degradation at 80 degC in EtOH solution measured up to 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607594	Cytotoxicity against human OE21 cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359352	Effect on tyrosinase expression in mouse Melan-a cells at 40 uM after 72 hrs by western blot analysis (Rvb = 1 No_unit)	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501407	Photochemical stability of the compound assessed as compound degradation under 254 nm UV-light exposure in EtOH solution measured after 24 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607598	Cytotoxicity against human LoVo cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359348	Decrease in tyrosinase mRNA expression in mouse Melan-a cells at 40 uM after 24 hrs by SYBR green dye based qRT-PCR analysis relative to control	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1347668	Inhibition of cell migration in human MDA-MB-231 cells at 100 uM after 24 hrs by inverted fluorescence microscopy based scratch assay relative to control	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501412	Thermal stability of the compound at 40 degC in EtOH solution after 3 to 4 days by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607600	Induction of human U373 cell death assessed as morphological changes at MTT assay-related IC50 after 72 hrs by quantitative video microscopy	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359355	Effect on MITF expression in mouse Melan-a cells at 40 uM after 72 hrs by western blot analysis (Rvb = 1 No_unit)	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1272821	Antileishmanial activity against stationary-phase promastigotes of Leishmania major MRHO/IR/75/ER assessed as parasite growth inhibition after 48 hrs by Neubar chamber method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Antileishmanial activity of novel indolyl-coumarin hybrids: Design, synthesis, biological evaluation, molecular docking study and in silico ADME prediction.
AID1359350	Decrease in TRP2 mRNA expression in mouse Melan-a cells at 40 uM after 24 hrs by SYBR green dye based qRT-PCR analysis relative to control	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1347664	Antiproliferative activity against human MDA-MB-231 cells at 1 nM to 100 uM after 24 hrs by MTT assay relative to control	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501415	Stability of the compound assessed as compound degradation in 3% H2O2 solution at 40 degC in EtOH solution after 24 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501410	Thermal stability of the compound assessed as compound degradation at 40 degC in EtOH solution after 48 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359343	Inhibition of melanogenesis in mouse Melan-a cells assessed as effect on pigmentation at 40 uM after 72 hrs by photography	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1359354	Effect on TRP1 expression in mouse Melan-a cells at 40 uM after 72 hrs by western blot analysis (Rvb = 1 No_unit)	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501418	Stability of the compound assessed as compound degradation in 0.1 M NaOH solution at room temperature in EtOH solution after 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359362	Antimelanogenic activity in mouse Melan-a cells assessed as inhibition of alpha-MSH-stimulated melanin synthesis at 40 uM measured after 72 hrs	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501438	Photostability of the compound assessed as parent compound remaining under sunlight exposed for 6 days in EtOH solution measured in presence of antioxidant DL-alpha-tocopherol acetate by TLC method	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607601	Cytotoxicity against human U373 cells assessed as growth inhibition at MTT assay-related IC50 by quantitative video microscopy relative to control	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1501435	Photostability of the compound assessed as parent compound remaining under sunlight exposed for 6 days in EtOH solution measured in presence of UV-A filter avobenzone by TLC method	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347657	Displacement of 2-[125I]iodomelatonin from human MT1 receptor expressed in CHO cell lysates after 1 hr by gamma counting analysis	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501417	Stability of the compound assessed as compound degradation in 3% H2O2 solution at 40 degC in EtOH solution after 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501440	Photostability of the compound assessed as parent compound remaining under sunlight exposed for 6 days in EtOH solution measured by TLC method	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501406	Photochemical stability of the compound assessed as compound degradation under sunlight in EtOH solution measured after 24 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID204671	Inhibitory activity against squalene hopene cyclase from Alicyclobacillus acidocaldarius expressed in Escherichia coli	2004	Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8	Farnesyloxycoumarins, a new class of squalene-hopene cyclase inhibitors.
AID683124	Inhibition of recombinant human 15-lipoxygenase by MBTH-DMAB method	2012	European journal of medicinal chemistry, Nov, Volume: 57	Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors.
AID1359336	Inhibition of melanogenesis in mouse Melan-a cells assessed as effect on whitening property measured after 48 hrs	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501408	Photochemical stability of the compound assessed as compound degradation under sunlight in EtOH solution measured after 4 days by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501427	Drug metabolism assessed as (6aR,6bS,12bS,12cR)-3,10-Bis-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyloxy)-6a,6b,12b,12c-tetrahydro-5,8-dioxa-dibenzo[a,i]biphenylene-6,7-dione formation under sunlight in EtOH solution after 4 days by TLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347661	Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1163510	Cytotoxicity against human PANC1 cells under nutrient-deprived condition after 24 hrs by WST8 dye based assay	2014	Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19	Synthesis and biological evaluation of isoprenylated coumarins as potential anti-pancreatic cancer agents.
AID1501409	Thermal stability of the compound assessed as compound degradation at 37 degC in EtOH solution after 48 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347660	Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT assay	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501426	Stability of the compound assessed as compound degradation in 0.1 M HCl solution at 60 to 80 degC using solid sample up to 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501432	Photostability of the compound assessed as parent compound remaining under sunlight exposed for 3 days in EtOH solution measured in presence of UV-A filter DHHB by TLC method	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607602	Chemical stability of the compound in MEM cell culture medium after 72 hrs at 37 degC	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359356	Effect on Rab27a expression in mouse Melan-a cells at 40 uM after 72 hrs by western blot analysis (Rvb = 1 No_unit)	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501420	Stability of the compound assessed as compound degradation in 0.1 M HCl solution at room temperature in EtOH solution after 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607596	Cytotoxicity against human PC3 cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359331	Cytotoxicity against mouse Melan-a cells assessed as effect on cell viability at 40 uM after 24 to 72 hrs by trypan blue exclusion assay	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID607595	Cytotoxicity against human A549 cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1347659	Antiproliferative activity against mouse mammary carcinoma cell after 24 hrs by MTT assay	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501416	Stability of the compound assessed as compound degradation in 3% H2O2 solution at room temperature in EtOH solution after 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359339	Inhibition of melanogenesis in mouse Melan-a cells assessed as reduction in melanin content at 40 uM	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1347669	Inhibition of cell migration in human BT549 cells at 100 uM after 24 hrs by inverted fluorescence microscopy based scratch assay relative to control	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501411	Thermal stability of the compound at 37 degC in EtOH solution after 3 to 4 days by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607597	Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359366	Binding affinity to ERbeta in mouse Melan-a cells	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501425	Stability of the compound assessed as compound degradation in 0.1 M NaOH solution at 60 to 80 degC using solid sample up to 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347665	Antiproliferative activity against human BT549 cells at 1 nM to 100 uM after 24 hrs by MTT assay relative to control	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1347663	Antiproliferative activity against mouse mammary carcinoma cell at 1 nM to 100 uM after 24 hrs by MTT assay relative to control	2017	Journal of natural products, 12-22, Volume: 80, Issue:12	Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1359341	Inhibition of melanogenesis in mouse Melan-a cells assessed as reduction in melanin content at 40 uM after 72 hrs relative to control	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID140324	Compound was tested for the inhibitory activity against mouse macrophage RAW 264.7 cells at the concentration of 50 uM; Inactive	2000	Bioorganic & medicinal chemistry letters, Jan-03, Volume: 10, Issue:1	1,1-Dimethylallylcoumarins potently suppress both lipopolysaccharide- and interferon-gamma-induced nitric oxide generation in mouse macrophage RAW 264.7 cells.
AID1501431	Photostability of the compound assessed as parent compound remaining under sunlight exposed for 3 days in EtOH solution measured in presence of UV-A filter avobenzone by TLC method	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359351	Decrease in MITF mRNA expression in mouse Melan-a cells at 40 uM after 24 hrs by SYBR green dye based qRT-PCR analysis relative to control	2018	European journal of medicinal chemistry, May-25, Volume: 152	Natural oxyprenylated coumarins are modulators of melanogenesis.
AID607593	Cytotoxicity against human U373 cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1501421	Stability of the compound assessed as compound degradation in 0.1 M HCl solution at 60 degC in EtOH solution after 24 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501414	Stability of the compound assessed as compound degradation in 3% H2O2 solution at room temperature in EtOH solution after 24 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501436	Photostability of the compound assessed as parent compound remaining under sunlight exposed for 6 days in EtOH solution measured in presence of UV-A filter DHHB by TLC method	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501424	Thermal stability of the compound assessed as compound degradation at 37 to 80 degC using solid samples after 96 hrs by HPLC analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (2.94)	18.7374
1990's	0 (0.00)	18.2507
2000's	7 (20.59)	29.6817
2010's	19 (55.88)	24.3611
2020's	7 (20.59)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (2.86%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	34 (97.14%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	2.06	1	monohydroxybenzoic acid	algal metabolite; plant metabolite
coumarin 2H-chromen-2-one: coumarin derivative	7.59	2	coumarins	fluorescent dye; human metabolite; plant metabolite
melatonin [no description available]	2.15	1	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
emodin Emodin: Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies.. emodin : A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.	2.06	1	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
pentamidine Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.	2.13	1	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic
resacetophenone resacetophenone: structure in first source. 2',4'-dihydroxyacetophenone : A dihydroxyacetophenone that is acetophenone carrying hydroxy substituents at positions 2' and 4'.	2.06	1	dihydroxyacetophenone; resorcinols	plant metabolite
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	2.06	1	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
imperatorin imperatorin: tumor necrosis factor antagonist; furanocoumarin from West African medicinal plant Clausena anisata; structure in Negwer, 5th ed, #3005. imperatorin : A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 8. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.	2.17	1	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
prenol [no description available]	2.1	1	alkenyl alcohol; prenols
3-hydroxy-1-benzopyran-2-one 3-hydroxycoumarin: Photoprotective from sea urchin gametes and embryonic cells; structure in first source. hydroxycoumarin : Any coumarin carrying at least one hydroxy substituent.	2.1	1	hydroxycoumarin
butylated hydroxytoluene 2,6-di-tert-butyl-4-methylphenol : A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.	2.13	1	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	7.25	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
2,4,6-trihydroxyacetophenone monoacetylphloroglucinol: structure in first source. 2',4',6'-trihydroxyacetophenone : A benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acidic glycans and glycopeptides.	2.06	1	aromatic ketone; benzenetriol; methyl ketone	MALDI matrix material; plant metabolite
isoimperatorin isoimperatorin: tumor necrosis factor antagonist isolated from Glehniae root. isoimperatorin : A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 5. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.	2.17	1	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
columbianetin, (s)-isomer (S)-columbianetin : The (S)-(+)-enantiomer of columbianetin.	2	1	columbianetin
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.05	1	nitrogen oxoacid
a-130a [no description available]	3.47	7
farnesol Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.	2.38	2	farnesol	plant metabolite
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	3.05	4	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	2.06	1	4-coumaric acid	food component; mouse metabolite; plant metabolite
geraniol [no description available]	2.1	1	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
isoliquiritigenin [no description available]	2.06	1	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
sesquiterpenes [no description available]	2.06	1
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.07	1	caffeic acid	geroprotector; mouse metabolite
coniferyl alcohol coniferyl alcohol: structure. coniferol : A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring.	2.06	1	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; plant metabolite; volatile oil component
aurapten aurapten: RN refers to (E)-isomer; structure given in first source. auraptene : A member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties.	5.24	14	coumarins; monoterpenoid	antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; dopaminergic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; gamma-secretase modulator; gastrointestinal drug; hepatoprotective agent; matrix metalloproteinase inhibitor; neuroprotective agent; plant metabolite; PPARalpha agonist; vulnerary
sinapyl alcohol sinapyl alcohol: has anti-inflammatory and antinociceptive properties; structure in first source. trans-sinapyl alcohol : Sinapyl alcohol in which the configuration of the propenyl double bond is E. It is one of the main monolignols.. sinapyl alcohol : A primary alcohol, being cinnamyl alcohol hydroxylated at C-4 and methoxylated at C-3 and -5.	2.06	1	sinapyl alcohol	monolignol
coniferaldehyde coniferaldehyde: from aqueous extract of Senra incana. coniferyl aldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.06	1	cinnamaldehydes; guaiacols; phenylpropanoid	antifungal agent; plant metabolite
sinapaldehyde sinapyl aldehyde: structure in first source. (E)-sinapaldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	2.06	1	cinnamaldehydes; dimethoxybenzene; phenols	antifungal agent; plant metabolite
butein [no description available]	2.13	1	chalcones; polyphenol	antineoplastic agent; antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor; geroprotector; hypoglycemic agent; plant metabolite; radiosensitizing agent; tyrosine kinase inhibitor
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	3.38	6	hydroxycoumarin	fluorescent probe; food component; plant metabolite
clausarin clausarin: isolated from Enkleia siamensis; structure given in first source	2	1
collinin collinin: the active principle of Zanthoxylum spp.; structure in first source	2.17	1
8-geranyloxypsoralen [no description available]	2.17	1	terpene lactone
licochalcone a licochalcone A: has both anti-inflammatory and antineoplastic activities; structure given in first source; isolated from root of Glycyrrhiza inflata; RN given refers to (E)-isomer	2.13	1	chalcones
osthenol osthenol: structure in first source. osthenol : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 8 has been replaced by a prenyl group.	2	1	hydroxycoumarin	antifungal agent; plant metabolite
lacinartin lacinartin: from Zanthoxylum schinifolium; structure in first source	2.51	2
2',4'-dihydroxychalcone 2',4'-dihydroxychalcone: RN given refers to (E)-isomer; RN for cpd without isomeric designation not available 6/89; structure given in first source	2.06	1
bergamottin bergamottin: constituent of bergamot oil; structure given in first source	2.17	1	furanocoumarin	metabolite
4-hydroxycordoin 4-hydroxycordoin: antibacterial and anti-inflammatory from Lonchocarpus neuroscapha Benth. (Fabaceae); structure in first source. 4-hydroxycordoin : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at position 4 and 2' and a (3-methylbut-2-en-1-yl)oxy group at position 4'. It has been isolated from Lonchocarpus neuroscapha.	2.06	1	aromatic ether; chalcones; polyphenol	anti-inflammatory agent; antibacterial agent; plant metabolite
derricidin derricidin: from Lonchocarpus sericeus; structure in first source	2.06	1	chalcones
o-geranylsinapyl alcohol O-geranylsinapyl alcohol: structure given in first source; isolated from the bark of Fagara rhetza, an Indonesian medicinal plant	2.06	1
5-geranyloxy-7-methoxycoumarin 5-geranyloxy-7-methoxycoumarin: structure in first source	2.17	1	terpene lactone
galbanic acid [no description available]	7.54	2	terpene lactone
nelumal a nelumal A: aromatase inhibitor from Ligularia nelumbifolia; structure in first source	2.06	1
farnesiferol c farnesiferol C: an antiangiogenic and antineoplastic agent; structure in first source	2.02	1
4'-geranyloxyferulic acid 4'-geranyloxyferulic acid: a colon cancer chemopreventive agent isolated from grapefruit skin; structure in first source	3.05	4
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.48	2	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	4.97	11	benzenes; hydroxycoumarin; methyl ketone
ferulenol ferulenol: intoxicating component of powdered Ferula communis variety brevifolia; RN given for (E,E)-isomer	2.02	1
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.1	1

Condition	Relationship Strength	Studies
Innate Inflammatory Response [description not available]	2.83	3
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	7.83	3
Cancer of Pancreas [description not available]	3.43	5
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	3.43	5
Breast Cancer [description not available]	2.15	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.15	1
Anoxemia [description not available]	2.41	1
ATLL [description not available]	2.41	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	7.41	1
Leukemia-Lymphoma, Adult T-Cell Aggressive T-Cell malignancy with adult onset, caused by HUMAN T-LYMPHOTROPIC VIRUS 1. It is endemic in Japan, the Caribbean basin, Southeastern United States, Hawaii, and parts of Central and South America and sub-Saharan Africa.	2.41	1
Lesion of Sciatic Nerve [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.51	2
Polyarthritis [description not available]	7.31	1
Adjuvant Arthritis [description not available]	2.31	1
Rheumatoid Arthritis [description not available]	2.31	1
Anasarca [description not available]	2.31	1
Arthritis Acute or chronic inflammation of JOINTS.	7.31	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.31	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.31	1
Metastase [description not available]	2.17	1
Angiogenesis, Pathologic [description not available]	2.17	1
Animal Mammary Carcinoma [description not available]	2.17	1
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.17	1
Cancer of Stomach [description not available]	2.21	1
Invasiveness, Neoplasm [description not available]	2.21	1
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.21	1
Carcinoma, Lewis Lung A carcinoma discovered by Dr. Margaret R. Lewis of the Wistar Institute in 1951. This tumor originated spontaneously as a carcinoma of the lung of a C57BL mouse. The tumor does not appear to be grossly hemorrhagic and the majority of the tumor tissue is a semifirm homogeneous mass. (From Cancer Chemother Rep 2 1972 Nov;(3)1:325) It is also called 3LL and LLC and is used as a transplantable malignancy.	2.1	1
Cancer of Lung [description not available]	2.1	1
Lung Neoplasms Tumors or cancer of the LUNG.	2.1	1
Papilloma, Squamous Cell [description not available]	2.05	1
Cancer of Skin [description not available]	2.05	1
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	2.05	1
Skin Neoplasms Tumors or cancer of the SKIN.	2.05	1
Carcinoma, Anaplastic [description not available]	2.04	1
Malignant Melanoma [description not available]	7.04	1
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.04	1
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	7.04	1

umbelliprenin

Description

Cross-References

Synonyms (29)

Research Excerpts

Overview

Effects

Toxicity

Drug Classes (1)

Protein Targets (16)

Potency Measurements

Inhibition Measurements

Other Measurements

Biological Processes (30)

Molecular Functions (10)

Ceullar Components (6)

Bioassays (95)

Research

Studies (34)

Market Indicators

Research Demand Index: 25.25

Study Types

umbelliprenin

Description

Cross-References

Synonyms (29)

Research Excerpts

Overview

Effects

Toxicity

Drug Classes (1)

Protein Targets (16)

Potency Measurements

Inhibition Measurements

Other Measurements

Biological Processes (30)

Molecular Functions (10)

Ceullar Components (6)

Bioassays (95)

Research

Studies (34)

Market Indicators

Research Demand Index: 25.25

Study Types

Related Drugs (51)

Related Conditions (37)