Compounds > 4'-geranyloxyferulic acid
Page last updated: 2024-11-13

4'-geranyloxyferulic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4'-geranyloxyferulic acid: a colon cancer chemopreventive agent isolated from grapefruit skin; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID39847023
CHEMBL ID221960
SCHEMBL ID18265477
MeSH IDM0550685

Synonyms (5)

Synonym
4'-geranyloxyferulic acid
CHEMBL221960 ,
bdbm50354139
(2e)-3-(4-{[(2e)-3,7-dimethylocta-2,6-dienyl]oxy}-3-methoxyphenyl)prop-2-enoic acid
SCHEMBL18265477

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"Among the compounds assayed, auraptene showed to possess potentialities to be a potent activator of both translocation of GLUT4 and glucose influx into skeletal muscle cells with the highest bioavailability among effective compounds."( The interaction of auraptene and other oxyprenylated phenylpropanoids with glucose transporter type 4.
Ashida, H; Daishi, S; Epifano, F; Fiorito, S; Genovese, S; Ikeda, M; Nakgano, T; Taddeo, VA; Yamashita, Y, 2017)		0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin G/H synthase 1Ovis aries (sheep)IC50 (µMol)54.20000.00032.177410.0000AID620575
Melatonin receptor type 1AHomo sapiens (human)Ki59.00000.00000.27359.1000AID1347657
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMelatonin receptor type 1AHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayMelatonin receptor type 1AHomo sapiens (human)
mating behaviorMelatonin receptor type 1AHomo sapiens (human)
circadian rhythmMelatonin receptor type 1AHomo sapiens (human)
G protein-coupled receptor signaling pathwayMelatonin receptor type 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
protein bindingMelatonin receptor type 1AHomo sapiens (human)
melatonin receptor activityMelatonin receptor type 1AHomo sapiens (human)
hormone bindingMelatonin receptor type 1AHomo sapiens (human)
organic cyclic compound bindingMelatonin receptor type 1AHomo sapiens (human)
G protein-coupled receptor activityMelatonin receptor type 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membraneMelatonin receptor type 1AHomo sapiens (human)
receptor complexMelatonin receptor type 1AHomo sapiens (human)
plasma membraneMelatonin receptor type 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (53)

Assay IDTitleYearJournalArticle
AID449573Anticonvulsant activity in mouse at 300 mg/kg, ip after 15 mins by MES test2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents.
AID449579Anticonvulsant activity in mouse after 30 mins by MES test2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents.
AID607600Induction of human U373 cell death assessed as morphological changes at MTT assay-related IC50 after 72 hrs by quantitative video microscopy2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1625341Activation of human TRPA1 expressed in HEK293 cells assessed as increase in calcium level at 20 uM by fura2/AM dye based single cell based plate reader analysis2016Journal of natural products, Apr-22, Volume: 79, Issue:4
Plumbagin, Juglone, and Boropinal as Novel TRPA1 Agonists.
AID349304Antimicrobial activity against Porphyromonas gingivalis ATCC 33277 assessed as inhibition of biofilm formation at 31.3 ug/ml after 48 hrs2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.
AID659713Agonist activity at human farnesoid X receptor expressed in human HepG2 cells at 10 uM after 24 hrs by dual-luciferase assay relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.
AID659714Agonist activity at human farnesoid X receptor expressed in human HepG2 cells at 25 uM after 24 hrs by dual-luciferase assay relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.
AID620575Inhibition of ovine COX1 using TMPD as substrate preincubated for 15 mins2011Bioorganic & medicinal chemistry letters, Oct-01, Volume: 21, Issue:19
Inhibition of COX-1 activity and COX-2 expression by 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its semi-synthetic derivatives.
AID1347664Antiproliferative activity against human MDA-MB-231 cells at 1 nM to 100 uM after 24 hrs by MTT assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1376901Agonist activity at AhR (unknown origin) expressed in mouse H1L1.1c2 cells at 1 to 100 uM after 8 to 10 hrs by luciferase reporter gene assay2017Journal of natural products, 06-23, Volume: 80, Issue:6
Interaction of 7-Alkoxycoumarins with the Aryl Hydrocarbon Receptor.
AID449576Anticonvulsant activity in mouse at 300 mg/kg, ip after 120 mins by MES test2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents.
AID349301Antimicrobial activity against Streptococcus mutans ATCC 25175 assessed as effect on bacterial growth after 4 hrs by XTT assay relative to control2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.
AID449574Anticonvulsant activity in mouse at 300 mg/kg, ip after 30 mins by MES test2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents.
AID607593Cytotoxicity against human U373 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID349295Antimicrobial activity against Porphyromonas gingivalis ATCC 33277 assessed as bacterial growth at 15.6 ug/ml after 4 hrs by XTT assay relative to control2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.
AID746653Cytotoxicity against mouse RAW264.7 cells by MTT assay2013Bioorganic & medicinal chemistry letters, May-15, Volume: 23, Issue:10
Conjugation of l-NAME to prenyloxycinnamic acids improves its inhibitory effects on nitric oxide production.
AID1347663Antiproliferative activity against mouse mammary carcinoma cell at 1 nM to 100 uM after 24 hrs by MTT assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID746654Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess method2013Bioorganic & medicinal chemistry letters, May-15, Volume: 23, Issue:10
Conjugation of l-NAME to prenyloxycinnamic acids improves its inhibitory effects on nitric oxide production.
AID607595Cytotoxicity against human A549 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID607594Cytotoxicity against human OE21 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID620577Antiinflammatory activity in human monocytes assessed as inhibition of LPS-induced COX2 expression after 20 hrs using rabbit polyclonal antibody IgG by Western blot analysis2011Bioorganic & medicinal chemistry letters, Oct-01, Volume: 21, Issue:19
Inhibition of COX-1 activity and COX-2 expression by 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its semi-synthetic derivatives.
AID276338Antimicrobial activity against Helicobacter pylori DSMZ 48672006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
In vitro inhibitory activity of boropinic acid against Helicobacter pylori.
AID607598Cytotoxicity against human LoVo cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID349294Antimicrobial activity against Porphyromonas gingivalis ATCC 33277 assessed as bacterial growth at 31.2 ug/ml after 4 hrs by XTT assay relative to control2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.
AID349296Antimicrobial activity against Porphyromonas gingivalis ATCC 33277 assessed as bacterial growth at 7.8 ug/ml after 4 hrs by XTT assay relative to control2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.
AID349293Antimicrobial activity against Porphyromonas gingivalis ATCC 33277 assessed as bacterial growth at 62.5 ug/ml after 4 hrs by XTT assay relative to control2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.
AID1347662Antiproliferative activity against human MCF7 cells at 1 nM to 100 uM after 24 hrs by MTT assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID449577Anticonvulsant activity in mouse after 5 mins by MES test2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents.
AID659711Agonist activity at human farnesoid X receptor expressed in human HepG2 cells at 1 uM after 24 hrs by dual-luciferase assay relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.
AID1347659Antiproliferative activity against mouse mammary carcinoma cell after 24 hrs by MTT assay2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID449580Anticonvulsant activity in mouse after 60 mins by MES test2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents.
AID349299Antimicrobial activity against Streptococcus mutans ATCC 25175 assessed as inhibition of biofilm formation at 3.9 ug/ml after 48 hrs2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.
AID607596Cytotoxicity against human PC3 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID659715Agonist activity at human farnesoid X receptor expressed in human HepG2 cells at 50 uM after 24 hrs by dual-luciferase assay relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.
AID620576Inhibition of ovine COX2 using TMPD as substrate at 300 uM preincubated for 15 mins2011Bioorganic & medicinal chemistry letters, Oct-01, Volume: 21, Issue:19
Inhibition of COX-1 activity and COX-2 expression by 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its semi-synthetic derivatives.
AID659710Agonist activity at human farnesoid X receptor expressed in human HepG2 cells at 0.1 uM after 24 hrs by dual-luciferase assay relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.
AID1376904Antagonist activity at AhR (unknown origin) expressed in mouse H1L1.1c2 cells assessed as inhibition of FICZ-induced AhR activation at 1 to 100 uM after 8 to 10 hrs by luciferase reporter gene assay2017Journal of natural products, 06-23, Volume: 80, Issue:6
Interaction of 7-Alkoxycoumarins with the Aryl Hydrocarbon Receptor.
AID620569Antiinflammatory activity in human monocytes assessed as inhibition of LPS-induced COX2 expression at 100 uM after 20 hrs using rabbit polyclonal antibody IgG by SDS-PAGE analysis2011Bioorganic & medicinal chemistry letters, Oct-01, Volume: 21, Issue:19
Inhibition of COX-1 activity and COX-2 expression by 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its semi-synthetic derivatives.
AID659716Agonist activity at human farnesoid X receptor expressed in human HepG2 cells at 100 uM after 24 hrs by dual-luciferase assay relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.
AID349297Antimicrobial activity against Porphyromonas gingivalis ATCC 33277 assessed as bacterial growth at 3.9 ug/ml after 4 hrs by XTT assay relative to control2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.
AID1347660Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT assay2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID349291Antimicrobial activity against Porphyromonas gingivalis ATCC 33277 assessed as bacterial growth at 250 ug/ml after 4 hrs by XTT assay relative to control2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.
AID607601Cytotoxicity against human U373 cells assessed as growth inhibition at MTT assay-related IC50 by quantitative video microscopy relative to control2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1347665Antiproliferative activity against human BT549 cells at 1 nM to 100 uM after 24 hrs by MTT assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID659717Agonist activity at human farnesoid X receptor expressed in human HepG2 cells after 24 hrs by dual-luciferase assay relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.
AID1347657Displacement of 2-[125I]iodomelatonin from human MT1 receptor expressed in CHO cell lysates after 1 hr by gamma counting analysis2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1347661Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID349292Antimicrobial activity against Porphyromonas gingivalis ATCC 33277 assessed as bacterial growth at 125 ug/ml after 4 hrs by XTT assay relative to control2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.
AID607597Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID309363Antiinflammatory activity in CD1 mouse assessed as inhibition of croton oil-induced ear oedema at 0.3 umol/cm^2 after 6 hrs2007Bioorganic & medicinal chemistry letters, Oct-15, Volume: 17, Issue:20
Synthesis and anti-inflammatory activity of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives.
AID620573Antiinflammatory activity in human monocytes assessed as inhibition of LPS-induced COX2 expression at 10 uM after 20 hrs using rabbit polyclonal antibody IgG by Western blot analysis2011Bioorganic & medicinal chemistry letters, Oct-01, Volume: 21, Issue:19
Inhibition of COX-1 activity and COX-2 expression by 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its semi-synthetic derivatives.
AID659712Agonist activity at human farnesoid X receptor expressed in human HepG2 cells at 5 uM after 24 hrs by dual-luciferase assay relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.
AID449578Anticonvulsant activity in mouse after 15 mins by MES test2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (15.38)29.6817
2010's20 (76.92)24.3611
2020's2 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.79

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.79 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.79)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
4-hydroxybenzoic acid
4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.		2.0610monohydroxybenzoic acidalgal metabolite;
plant metabolite
coumarin
2H-chromen-2-one: coumarin derivative		2.2510coumarinsfluorescent dye;
human metabolite;
plant metabolite
salicylic acid
Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).		2.0310monohydroxybenzoic acidalgal metabolite;
antifungal agent;
antiinfective agent;
EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor;
keratolytic drug;
plant hormone;
plant metabolite
guaiacol
Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.		2.0310guaiacolsdisinfectant;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
expectorant;
plant metabolite
hydroquinone
[no description available]		2.4420benzenediol;
hydroquinones		antioxidant;
carcinogenic agent;
cofactor;
Escherichia coli metabolite;
human xenobiotic metabolite;
mouse metabolite;
skin lightening agent
melatonin
[no description available]		2.1510acetamides;
tryptamines		anticonvulsant;
central nervous system depressant;
geroprotector;
hormone;
human metabolite;
immunological adjuvant;
mouse metabolite;
radical scavenger
acetaminophen
Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.		2.0310acetamides;
phenols		antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
cyclooxygenase 3 inhibitor;
environmental contaminant;
ferroptosis inducer;
geroprotector;
hepatotoxic agent;
human blood serum metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic
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.		2.0610trihydroxyanthraquinoneantineoplastic agent;
laxative;
plant metabolite;
tyrosine kinase inhibitor
indomethacin
Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.		2.4620aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
juglone
juglone: structure. juglone : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities.		2.1310hydroxy-1,4-naphthoquinonegeroprotector;
herbicide;
reactive oxygen species generator
mesalamine
Mesalamine: An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed). mesalamine : A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.		3.1710amino acid;
aromatic amine;
monocarboxylic acid;
monohydroxybenzoic acid;
phenols		non-steroidal anti-inflammatory drug
metronidazole
Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.		2.0310C-nitro compound;
imidazoles;
primary alcohol		antiamoebic agent;
antibacterial drug;
antimicrobial agent;
antiparasitic agent;
antitrichomonal drug;
environmental contaminant;
prodrug;
radiosensitizing agent;
xenobiotic
allyl isothiocyanate
allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.		2.1310alkenyl isothiocyanate;
isothiocyanate		antimicrobial agent;
antineoplastic agent;
apoptosis inducer;
lachrymator;
metabolite
arginine
Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.		7.2110arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical
lawsone
lawsone: a molluscacide from leaves of Lawsonia inermis L. topical sunscreening agent; structure; powdered leaves of Lawsonia inermis(Lythraceae) used as brown hair dye. lawsone : 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.		2.7530
2,6-dihydroxyanthraquinone
2,6-dihydroxyanthraquinone: structure given in first source. anthraflavic acid : A dihydroxyanthraquinone that is anthracene substituted by hydroxy groups at C-3 and C-7 and oxo groups at C-9 and C-10.		2.0310dihydroxyanthraquinoneantimutagen;
plant metabolite
resacetophenone
resacetophenone: structure in first source. 2',4'-dihydroxyacetophenone : A dihydroxyacetophenone that is acetophenone carrying hydroxy substituents at positions 2' and 4'.		2.0610dihydroxyacetophenone;
resorcinols		plant metabolite
1-phenylpropanol
1-phenylpropanol: structure in first source		2.1310organic molecular entity
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.		2.4520methoxybenzoic acid;
monohydroxybenzoic acid		plant metabolite
chenodeoxycholic acid
Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.		2.0710bile acid;
C24-steroid;
dihydroxy-5beta-cholanic acid		human metabolite;
mouse metabolite
plumbagin
plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.		2.1310hydroxy-1,4-naphthoquinone;
phenols		anticoagulant;
antineoplastic agent;
immunological adjuvant;
metabolite
herniarin
herniarin: methoxy analog of umbelliferone; structure. herniarin : A member of the class of coumarins that is coumarin substituted by a methoxy group at position 7.		2.1510coumarinsfluorochrome
amoxicillin
Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.		2.0310penicillin allergen;
penicillin		antibacterial drug
7-ethoxycoumarin
7-ethoxycoumarin : A member of the class of coumarins that is umbelliferone in which the hydroxy group at position 7 is replaced by an ethoxy group.		2.1510aromatic ether;
coumarins
ng-nitroarginine methyl ester
NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.		2.4920alpha-amino acid ester;
L-arginine derivative;
methyl ester;
N-nitro compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor
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.		2.0610aromatic ketone;
benzenetriol;
methyl ketone		MALDI matrix material;
plant metabolite
clarithromycin
Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.		2.0310macrolide antibioticantibacterial drug;
environmental contaminant;
protein synthesis inhibitor;
xenobiotic
a-130a
[no description available]		3.1850
naringenin
(S)-naringenin : The (S)-enantiomer of naringenin.		2.0310(2S)-flavan-4-one;
naringenin		expectorant;
plant metabolite
nitroarginine
Nitroarginine: An inhibitor of nitric oxide synthetase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. (Neurochem Res 1995:200(4):451-6). N(gamma)-nitro-L-arginine : An L-arginine derivative that is L-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group.		2.110guanidines;
L-arginine derivative;
N-nitro compound;
non-proteinogenic L-alpha-amino acid
betadex
beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.		2.1310cyclodextrin
ferulic acid
ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.		3.6280ferulic acidsanti-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.		2.06104-coumaric acidfood component;
mouse metabolite;
plant metabolite
isoliquiritigenin
[no description available]		2.0610chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist
caffeic acid
trans-caffeic acid : The trans-isomer of caffeic acid.		2.0310caffeic acidgeroprotector;
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.		2.0610guaiacols;
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.		10.22140coumarins;
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
umbelliprenin
umbelliprenin: RN given refers to cpd with unspecified isomeric designation		3.0540terpene lactone
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.		2.0610sinapyl alcoholmonolignol
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.		2.0610cinnamaldehydes;
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.		2.0610cinnamaldehydes;
dimethoxybenzene;
phenols		antifungal agent;
plant metabolite
7-hydroxycoumarin
7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.		3.6280hydroxycoumarinfluorescent probe;
food component;
plant metabolite
collinin
collinin: the active principle of Zanthoxylum spp.; structure in first source		2.4620
lacinartin
lacinartin: from Zanthoxylum schinifolium; structure in first source		2.7530
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		2.0610
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.		2.7530aromatic ether;
chalcones;
polyphenol		anti-inflammatory agent;
antibacterial agent;
plant metabolite
derricidin
derricidin: from Lonchocarpus sericeus; structure in first source		2.4620chalcones
o-geranylsinapyl alcohol
O-geranylsinapyl alcohol: structure given in first source; isolated from the bark of Fagara rhetza, an Indonesian medicinal plant		2.4720
chlorhexidine
Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.		2.0410biguanides;
monochlorobenzenes		antibacterial agent;
antiinfective agent
nelumal a
nelumal A: aromatase inhibitor from Ligularia nelumbifolia; structure in first source		2.4720
tetracycline
Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.		2.0310
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.		4.7580benzenes;
hydroxycoumarin;
methyl ketone
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		03.0140
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.		08.0140
Absence Seizure
[description not available]		02.0510
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		02.0510
Hepatocellular Carcinoma
[description not available]		02.1510
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.1510
Breast Cancer
[description not available]		02.1510
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.1510
Cancer of Colon
[description not available]		03.4820
Colonic Neoplasms
Tumors or cancer of the COLON.		03.4820
Benign Neoplasms
[description not available]		02.2110
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.2110
Carcinogenesis
The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.		07.110
Adenocarcinoma, Basal Cell
[description not available]		02.110
Adenoma, Basal Cell
[description not available]		02.110
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.110
Colorectal Cancer
[description not available]		02.110
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		02.110
Adenoma
A benign epithelial tumor with a glandular organization.		02.110
Colorectal Neoplasms
Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.		02.110
Idiopathic Parkinson Disease
[description not available]		02.1310
Parkinson Disease
A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)		02.1310
Colonic Diseases
Pathological processes in the COLON region of the large intestine (INTESTINE, LARGE).		07.9910