Compounds > methyl ferulate
Page last updated: 2024-11-11

methyl ferulate

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

Description

methyl ferulate: inhibits LDL oxidation; isolated from Chrysanthemum coronarium; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

trans-methylferulate : A cinnamate ester that is the methyl ester of ferulic acid. It has been isolated from Pisonia aculeata. [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]

FloraRankFlora DefinitionFamilyFamily Definition
Pisoniagenus[no description available]NyctaginaceaeA plant family of the order Caryophyllales, subclass Caryophyllidae, class Magnoliopsida.[MeSH]
ChrysanthemumgenusA plant genus of the family ASTERACEAE. The common names of daisy or marguerite are easily confused with other plants. Some species in this genus have been reclassified to TANACETUM.[MeSH]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

Cross-References

ID SourceID
PubMed CID5357283
CHEMBL ID32969
CHEBI ID67379
MeSH IDM0523988

Synonyms (66)

Synonym
methyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
22329-76-6
EN300-28623
AKOS003404666
2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester
brn 2731141
nsc 74548
ai3-23713
cinnamic acid, 4-hydroxy-3-methoxy-, methyl ester
methyl ferulate
2309-07-1
nsc-74548
nsc74548
ferulic acid methyl ester
ferulic acid methylester
chebi:67379 ,
CHEMBL32969 ,
BMSE000609
methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
BMSE010229
methyl 4-hydroxy-3-methoxycinnamate
methyl (e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
STK665368
4-10-00-01779 (beilstein handbook reference)
3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid methyl ester
4-hydroxy-3-methoxy-cinnamic acid methyl ester
methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)acrylate
trans-methylferulate
S5451
AKOS025310509
methyl(e)-3-(4-hydroxy-3-methoxyphenyl)acrylate
(e)4-hydroxy-3-methoxycinnamic acid methyl ester
methyl (e)-3-(4-hydroxy-3-methoxyphenyl)acrylate
methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
methyl (e)-4-hydroxy-3-methoxycinnamate
methyl (e)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
methyl(2e)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
(e)-4-hydroxy-3-methoxycinnamic acid methyl ester
ferulicacidmethylester
methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate #
CS-W019429
trans-ferulic acid methyl ester
methyl 4'-hydroxy-3'-methoxycinnamate
Y98BUA66RX ,
methyl ferulate, (e)-
methyl trans-ferulate
2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester, (2e)-
methyl (e)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate
mfcd00017208
GS-3694
Z18704892
J-014979
4-hydroxy-3-methoxycinnamic acid methyl ester
Q27135838
HY-W018643
(e)-methyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
bdbm50236705
CCG-266639
szq ,
methyl (~{e})-3-(3-methoxy-4-oxidanyl-phenyl)prop-2-enoate
O11884
unii-y98bua66rx
BS-48861
A918603
(e)-ferulic acid methyl ester

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
"C57BL/6 mice were divided into a control group,a model group, and Methyl ferulic acid with high dosage (20 mg/kg), moderate dosage (10 mg/kg) and low dosage (5 mg/kg) groups."( Hepatoprotective effects of Methyl ferulic acid on alcohol-induced liver oxidative injury in mice by inhibiting the NOX4/ROS-MAPK pathway.
Chen, L; Li, C; Li, L; Li, YW; Shi, L; Wu, D; Yang, CF; Zhong, YJ, 2017)		0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role 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]

Drug Classes (3)

ClassDescription
cinnamate ester
methyl esterAny carboxylic ester resulting from the formal condensation of a carboxy group with methanol.
guaiacolsAny phenol carrying an additional methoxy substituent at the ortho-position.
[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 Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bifunctional epoxide hydrolase 2Homo sapiens (human)IC50 (µMol)1.80000.00000.54509.1000AID1443219
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Substance-P receptorCavia porcellus (domestic guinea pig)CD83.00000.90004.50009.8000AID144377
Quinone oxidoreductaseMus musculus (house mouse)CD83.00000.20002.74219.8000AID144377
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
response to toxic substanceBifunctional epoxide hydrolase 2Homo sapiens (human)
positive regulation of gene expressionBifunctional epoxide hydrolase 2Homo sapiens (human)
dephosphorylationBifunctional epoxide hydrolase 2Homo sapiens (human)
cholesterol homeostasisBifunctional epoxide hydrolase 2Homo sapiens (human)
stilbene catabolic processBifunctional epoxide hydrolase 2Homo sapiens (human)
phospholipid dephosphorylationBifunctional epoxide hydrolase 2Homo sapiens (human)
regulation of cholesterol metabolic processBifunctional epoxide hydrolase 2Homo sapiens (human)
epoxide metabolic processBifunctional epoxide hydrolase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
magnesium ion bindingBifunctional epoxide hydrolase 2Homo sapiens (human)
epoxide hydrolase activityBifunctional epoxide hydrolase 2Homo sapiens (human)
toxic substance bindingBifunctional epoxide hydrolase 2Homo sapiens (human)
phosphatase activityBifunctional epoxide hydrolase 2Homo sapiens (human)
10-hydroxy-9-(phosphonooxy)octadecanoate phosphatase activityBifunctional epoxide hydrolase 2Homo sapiens (human)
lipid phosphatase activityBifunctional epoxide hydrolase 2Homo sapiens (human)
protein homodimerization activityBifunctional epoxide hydrolase 2Homo sapiens (human)
lysophosphatidic acid phosphatase activityBifunctional epoxide hydrolase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
peroxisomeBifunctional epoxide hydrolase 2Homo sapiens (human)
peroxisomal matrixBifunctional epoxide hydrolase 2Homo sapiens (human)
cytosolBifunctional epoxide hydrolase 2Homo sapiens (human)
extracellular exosomeBifunctional epoxide hydrolase 2Homo sapiens (human)
peroxisomeBifunctional epoxide hydrolase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (56)

Assay IDTitleYearJournalArticle
AID1686256Neuroprotection in human SH-SY5Y cells assessed as reduction in beta-amyloid peptide (1-42)-induced cell death at 1 uM incubated for 24 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
The Antioxidant Additive Approach for Alzheimer's Disease Therapy: New Ferulic (Lipoic) Acid Plus Melatonin Modified Tacrines as Cholinesterases Inhibitors, Direct Antioxidants, and Nuclear Factor (Erythroid-Derived 2)-Like 2 Activators.
AID1295744Antioxidant activity assessed as DPPH radical scavenging activity at 1.67 uM measured as absorbance (t -> infinity) after 10 secs by UV-visible spectrophotometry2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID684449Cytotoxicity against human HeLa cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1686255Neuroprotection in human SH-SY5Y cells assessed as reduction in beta-amyloid peptide (1-42)-induced cell death at 3 uM incubated for 24 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
The Antioxidant Additive Approach for Alzheimer's Disease Therapy: New Ferulic (Lipoic) Acid Plus Melatonin Modified Tacrines as Cholinesterases Inhibitors, Direct Antioxidants, and Nuclear Factor (Erythroid-Derived 2)-Like 2 Activators.
AID1295737Antioxidant activity assessed as superoxide anion radical scavenging activity at 80 uM measured as rate constant recorded every min for 7 mins by nitroblue tetrazolium assay (Rvb = 0.188 +/- 0.001 /min)2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID1070389Neuroprotective activity in mouse HT22 cells assessed as reduction of t-BOOH-induced oxidative stress at 40 uM preincubated for 3 hrs followed by t-BOOH induction measured for 20 hrs by time-resolved ECIS analysis2014Journal of natural products, Mar-28, Volume: 77, Issue:3
Flavonoids, flavonoid metabolites, and phenolic acids inhibit oxidative stress in the neuronal cell line HT-22 monitored by ECIS and MTT assay: a comparative study.
AID1355970Cytotoxicity against human A549 cells by MTT assay2018Journal of natural products, 07-27, Volume: 81, Issue:7
Bioactive Phenolic Components from the Twigs of Atalantia buxifolia.
AID684443Cytotoxicity against human HOP62 cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID290547Antitumor activity against KB cells by MTT assay2007Bioorganic & medicinal chemistry letters, May-15, Volume: 17, Issue:10
Synthesis and biological evaluation of 12 allenic aromatic ethers.
AID82003Cell viability in TPA-induced superoxide (O2-) generation in human promyelocytic leukemia HL-60 cells, at 100 uM concentration2000Bioorganic & medicinal chemistry letters, Jul-03, Volume: 10, Issue:13
Synthesis of feruloyl-myo-inositols and their inhibitory effects on superoxide generation.
AID1686260Neuroprotection in human SH-SY5Y cells assessed as reduction in H2O2-induced cell death at 3 uM incubated for 24 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
The Antioxidant Additive Approach for Alzheimer's Disease Therapy: New Ferulic (Lipoic) Acid Plus Melatonin Modified Tacrines as Cholinesterases Inhibitors, Direct Antioxidants, and Nuclear Factor (Erythroid-Derived 2)-Like 2 Activators.
AID1295743Antioxidant activity assessed as DPPH radical scavenging activity measured as rate constant after 10 secs by UV-visible spectrophotometry2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID1355968Cytotoxicity against human HepG2 cells by MTT assay2018Journal of natural products, 07-27, Volume: 81, Issue:7
Bioactive Phenolic Components from the Twigs of Atalantia buxifolia.
AID684450Cytotoxicity against human M4E cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID684440Cytotoxicity against human H460 cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1099186Antimicrobial activity against Athelia rolfsii assessed as growth inhibition at 100 ppm by agar dilution method1996Bioscience, biotechnology, and biochemistry, May, Volume: 60, Issue:5
Synthesis and antifungal activity of cinnamic acid esters.
AID684441Cytotoxicity against human NCI-H1792 cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1070390Cytotoxicity against mouse HT22 cells assessed as cell viability at 40 uM after 24 hrs by MTT assay2014Journal of natural products, Mar-28, Volume: 77, Issue:3
Flavonoids, flavonoid metabolites, and phenolic acids inhibit oxidative stress in the neuronal cell line HT-22 monitored by ECIS and MTT assay: a comparative study.
AID684439Cytotoxicity against human NCI-H157 cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1686252Neuroprotection in human SH-SY5Y cells assessed as reduction in beta-amyloid peptide (1-40)-induced cell death at 3 uM incubated for 24 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
The Antioxidant Additive Approach for Alzheimer's Disease Therapy: New Ferulic (Lipoic) Acid Plus Melatonin Modified Tacrines as Cholinesterases Inhibitors, Direct Antioxidants, and Nuclear Factor (Erythroid-Derived 2)-Like 2 Activators.
AID1070388Neuroprotective activity in mouse HT22 cells assessed as reduction of t-BOOH-induced oxidative stress at 40 uM preincubated for 3 hrs followed by t-BOOH induction measured after 20 hrs by MTT assay2014Journal of natural products, Mar-28, Volume: 77, Issue:3
Flavonoids, flavonoid metabolites, and phenolic acids inhibit oxidative stress in the neuronal cell line HT-22 monitored by ECIS and MTT assay: a comparative study.
AID1295745Antioxidant activity assessed as DPPH radical scavenging activity at 16.7 uM measured as absorbance (t -> infinity) after 10 secs by UV-visible spectrophotometry2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID684448Cytotoxicity against human M14 cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1233173Antimicrobial activity against Escherichia coli after 5 to 12 hrs by micro broth dilution assay2015Bioorganic & medicinal chemistry letters, Jul-01, Volume: 25, Issue:13
Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs.
AID684446Cytotoxicity against human Calu1 cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1295740Antioxidant activity assessed as superoxide anion radical scavenging activity at 80 uM measured as absorbance (t > infinity) recorded every min for 7 mins by nitroblue tetrazolium assay (Rvb = 1.9 +/- 0.01 No_unit)2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID1295736Antioxidant activity assessed as superoxide anion radical scavenging activity at 40 uM measured as rate constant recorded every min for 7 mins by nitroblue tetrazolium assay (Rvb = 0.188 +/- 0.001 /min)2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID82327Inhibitory activity against TPA-induced superoxide (O2-) generation in human promyelocytic leukemia HL-60 cells, at 100 uM concentration2000Bioorganic & medicinal chemistry letters, Jul-03, Volume: 10, Issue:13
Synthesis of feruloyl-myo-inositols and their inhibitory effects on superoxide generation.
AID1686251Neuroprotection in human SH-SY5Y cells assessed as reduction in beta-amyloid peptide (1-40)-induced cell death at 1 uM incubated for 24 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
The Antioxidant Additive Approach for Alzheimer's Disease Therapy: New Ferulic (Lipoic) Acid Plus Melatonin Modified Tacrines as Cholinesterases Inhibitors, Direct Antioxidants, and Nuclear Factor (Erythroid-Derived 2)-Like 2 Activators.
AID1295738Antioxidant activity assessed as superoxide anion radical scavenging activity at 160 uM measured as rate constant recorded every min for 7 mins by nitroblue tetrazolium assay (Rvb = 0.188 +/- 0.001 /min)2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID684451Cytotoxicity against human SKBR cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1532763Induction of insulin-stimulated 2-NBDG uptake in TNF-alpha-induced insulin resistant mouse 3T3L1 cells at 10 uM preincubated for 48 hrs followed by 2-NBDG addition measured after 30 mins in presence of insulin by fluorescence assay2019European journal of medicinal chemistry, Jan-15, Volume: 162Design and synthesis of rosiglitazone-ferulic acid-nitric oxide donor trihybrids for improving glucose tolerance.
AID1443219Inhibition of sEH (unknown origin) using PHOME as substrate after 40 mins by fluorescence photometric method2017Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8
Soluble epoxide hydrolase inhibitors of indolinone alkaloids and phenolic derivatives from Cimicifuga dahurica (Turcz.) Maxim.
AID684438Cytotoxicity against human A549 cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1295735Antioxidant activity assessed as hydroxyl radical scavenging activity at 15 uM by ESR spin trapping assay2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID1443220Mixed type inhibition of sEH (unknown origin) at 0.78 to 6.25 uM using PHOME as substrate measured for 30 mins by Lineweaver-burk plot method2017Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8
Soluble epoxide hydrolase inhibitors of indolinone alkaloids and phenolic derivatives from Cimicifuga dahurica (Turcz.) Maxim.
AID1686264Neuroprotection in human SH-SY5Y cells assessed as reduction in Rotenone/Oligomycin A -induced cell death at 3 uM incubated for 24 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
The Antioxidant Additive Approach for Alzheimer's Disease Therapy: New Ferulic (Lipoic) Acid Plus Melatonin Modified Tacrines as Cholinesterases Inhibitors, Direct Antioxidants, and Nuclear Factor (Erythroid-Derived 2)-Like 2 Activators.
AID684442Cytotoxicity against human H266 cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID144377Ability to induce NAD(P)H quinone reductase activity in cultured Hepa 1c1c7 murine hepatoma cells.1998Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26
Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related Michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers.
AID1659735Hypolipidemic activity in human HepG2 cells assessed as inhibition of oleic acid-induced lipid accumulation at 10 uM2020Bioorganic & medicinal chemistry letters, 06-01, Volume: 30, Issue:11
Hypolipidemic constituents from the aerial portion of Sibiraea angustata.
AID1355969Cytotoxicity against human MDA-MB-231 cells by MTT assay2018Journal of natural products, 07-27, Volume: 81, Issue:7
Bioactive Phenolic Components from the Twigs of Atalantia buxifolia.
AID1295747Antioxidant activity assessed as hydroxyl radical scavenging activity at 1.5 uM by ESR spin trapping assay2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID684447Cytotoxicity against human LOXIMVI cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1686259Neuroprotection in human SH-SY5Y cells assessed as reduction in H2O2-induced cell death at 1 uM incubated for 24 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
The Antioxidant Additive Approach for Alzheimer's Disease Therapy: New Ferulic (Lipoic) Acid Plus Melatonin Modified Tacrines as Cholinesterases Inhibitors, Direct Antioxidants, and Nuclear Factor (Erythroid-Derived 2)-Like 2 Activators.
AID1686263Neuroprotection in human SH-SY5Y cells assessed as reduction in Rotenone/Oligomycin A -induced cell death at 1 uM incubated for 24 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
The Antioxidant Additive Approach for Alzheimer's Disease Therapy: New Ferulic (Lipoic) Acid Plus Melatonin Modified Tacrines as Cholinesterases Inhibitors, Direct Antioxidants, and Nuclear Factor (Erythroid-Derived 2)-Like 2 Activators.
AID1295739Antioxidant activity assessed as superoxide anion radical scavenging activity at 40 uM measured as absorbance (t > infinity) recorded every min for 7 mins by nitroblue tetrazolium assay (Rvb = 1.9 +/- 0.01 No_unit)2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID684445Cytotoxicity against human 292G cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1295734Antioxidant activity assessed as hydroxyl radical scavenging activity at 5 uM by ESR spin trapping assay2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID1295741Antioxidant activity assessed as superoxide anion radical scavenging activity at 160 uM measured as absorbance (t > infinity) recorded every min for 7 mins by nitroblue tetrazolium assay (Rvb = 1.9 +/- 0.01 No_unit)2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID1099189Antimicrobial activity against Pythium sp. assessed as growth inhibition at 100 ppm by agar dilution method1996Bioscience, biotechnology, and biochemistry, May, Volume: 60, Issue:5
Synthesis and antifungal activity of cinnamic acid esters.
AID290548Antitumor activity against KBv200 cells by MTT assay2007Bioorganic & medicinal chemistry letters, May-15, Volume: 17, Issue:10
Synthesis and biological evaluation of 12 allenic aromatic ethers.
AID1295746Antioxidant activity assessed as DPPH radical scavenging activity at 60 uM measured as absorbance (t -> infinity) after 10 secs by UV-visible spectrophotometry2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID1295748Antioxidant activity assessed as hydroxyl radical scavenging activity at 2.5 uM by ESR spin trapping assay2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources.
AID684444Cytotoxicity against human NCI-H1299 cells after 72 hrs by alamar blue assay2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.
AID1233172Antimicrobial activity against Staphylococcus aureus after 5 to 12 hrs by micro broth dilution assay2015Bioorganic & medicinal chemistry letters, Jul-01, Volume: 25, Issue:13
Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs.
AID1443218Inhibition of sEH (unknown origin) at 100 uM using PHOME as substrate after 40 mins by fluorescence photometric method relative to control2017Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8
Soluble epoxide hydrolase inhibitors of indolinone alkaloids and phenolic derivatives from Cimicifuga dahurica (Turcz.) Maxim.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (6.06)18.2507
2000's4 (12.12)29.6817
2010's20 (60.61)24.3611
2020's7 (21.21)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.32

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.32 (24.57)
Research Supply Index3.56 (2.92)
Research Growth Index5.55 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.32)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other34 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
4-hydroxybenzyl alcohol
4-hydroxybenzyl alcohol: the aglycone of gastrodin. p-hydroxybenzyl alcohol : A member of the class of benzyl alcohols that is benzyl alcohol substituted by a hydroxy group at position 4. It has been isolated from Arcangelisia gusanlung.		2.0310benzyl alcohols;
phenols		plant metabolite
4-hydroxybenzoic acid
4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.		2.0310monohydroxybenzoic acidalgal metabolite;
plant metabolite
beta-alanine
[no description available]		2.0810amino acid zwitterion;
beta-amino acid		agonist;
fundamental metabolite;
human metabolite;
inhibitor;
neurotransmitter
catechol
[no description available]		2.110catecholsallelochemical;
genotoxin;
plant metabolite
coumarin
2H-chromen-2-one: coumarin derivative		1.9910coumarinsfluorescent dye;
human metabolite;
plant metabolite
3,4-dihydroxyphenylacetic acid
3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.		2.110catechols;
dihydroxyphenylacetic acid		human metabolite
melatonin
[no description available]		2.1310acetamides;
tryptamines		anticonvulsant;
central nervous system depressant;
geroprotector;
hormone;
human metabolite;
immunological adjuvant;
mouse metabolite;
radical scavenger
phosphoric acid
phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.		2.2510phosphoric acidsalgal metabolite;
fertilizer;
human metabolite;
NMR chemical shift reference compound;
solvent
pyrogallol
benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.		2.1310benzenetriol;
phenolic donor		plant metabolite
catechin
[no description available]		2.110hydroxyflavan
tacrine
Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.		2.1310acridines;
aromatic amine		EC 3.1.1.7 (acetylcholinesterase) inhibitor
5-methoxypsoralen
5-Methoxypsoralen: A linear furanocoumarin that has phototoxic and anti-inflammatory properties, with effects similar to METHOXSALEN. It is used in PUVA THERAPY for the treatment of PSORIASIS.. 5-methoxypsoralen : A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5.		2.17105-methoxyfurocoumarin;
organic heterotricyclic compound;
psoralens		hepatoprotective agent;
plant metabolite
2-(4-morpholinyl)-8-phenyl-4h-1-benzopyran-4-one
2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one: specific inhibitor of phosphatidylinositol 3-kinase; structure in first source		2.1710chromones;
morpholines;
organochlorine compound		autophagy inhibitor;
EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor;
geroprotector
berlition
berlition: antioxidant preparation containing alpha-lipoic acid, used in the neuroprotective therapy of chronic brain ischemia for correction of free-radical processes. (R)-lipoic acid : The (R)-enantiomer of lipoic acid. A vitamin-like, C8 thia fatty acid with anti-oxidant properties.. lipoic acid : A heterocyclic thia fatty acid comprising pentanoic acid with a 1,2-dithiolan-3-yl group at the 5-position.		2.1310dithiolanes;
heterocyclic fatty acid;
lipoic acid;
thia fatty acid		cofactor;
nutraceutical;
prosthetic group
thymol
Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.		2.110monoterpenoid;
phenols		volatile oil component
methylparaben
methylparaben: used as a preservative in cosmetics but potentiates UV-induced damage of skin; RN given refers to parent cpd. methylparaben : A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blueberries.		2.4820parabenantifungal agent;
antimicrobial food preservative;
neuroprotective agent;
plant metabolite
acrolein
[no description available]		2.1510enalherbicide;
human xenobiotic metabolite;
toxin
4-methylcatechol
[no description available]		2.110methylcatecholantioxidant;
carcinogenic agent;
hapten;
human metabolite;
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.		2.1710psoralensEC 3.1.1.7 (acetylcholinesterase) inhibitor;
metabolite
3-hydroxybenzeneacetic acid
3-hydroxybenzeneacetic acid: metabolite of L-dopa; structure. 3-hydroxyphenylacetic acid : A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group.		2.110monocarboxylic acid;
phenols		human xenobiotic metabolite
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.		1.9910hydroxycoumarin
2-tert-butylhydroquinone
2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.		2.1310hydroquinonesfood antioxidant
o,o-diisopropyl-s-benzylthiophosphate
O,O-diisopropyl-S-benzylthiophosphate: structure. iprobenfos : An organic thiophosphate that is the S-benzyl O,O-diisopropyl ester of phosphorothioic acid. Used as a rice fungicide to control leaf and ear blast, stem rot and sheath blight.		1.9910organic thiophosphateantifungal agrochemical;
phospholipid biosynthesis inhibitor
colforsin
Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.		2.2110acetate ester;
cyclic ketone;
labdane diterpenoid;
organic heterotricyclic compound;
tertiary alpha-hydroxy ketone;
triol		adenylate cyclase agonist;
anti-HIV agent;
antihypertensive agent;
plant metabolite;
platelet aggregation inhibitor;
protein kinase A agonist
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		2.0410adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
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.		2.1710psoralensEC 3.1.1.7 (acetylcholinesterase) inhibitor;
metabolite
seselin
seselin: structure in first source		2.1710coumarinsmetabolite
3-acetylcoumarin
3-acetylcoumarin: structure given in first source. 3-acetylcoumarin : A member of the class of coumarins that is coumarin in which the hydrogen at position 3 is replaced by an acetyl group.		1.9910coumarins
rosiglitazone
[no description available]		2.2110aminopyridine;
thiazolidinediones		EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor;
ferroptosis inhibitor;
insulin-sensitizing drug
phellopterin
phellopterin: a naturally occurring furanocoumarin found in roots of Angelica dahurica; structure in first source		2.110psoralens
prunasin
prunasin: cyanogenic glycoside; RN given refers to cpd without isomeric designation		2.0410prunasin
dabigatran
Dabigatran: A THROMBIN inhibitor which acts by binding and blocking thrombogenic activity and the prevention of thrombus formation. It is used to reduce the risk of stroke and systemic EMBOLISM in patients with nonvalvular atrial fibrillation.. dabigatran : An aromatic amide obtained by formal condensation of the carboxy group of 2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazole-5-carboxylic acid with the secondary amoino group of N-pyridin-2-yl-beta-alanine. The active metabolite of the prodrug dabigatran etexilate, it acts as an anticoagulant which is used for the prevention of stroke and systemic embolism.		7.0810aromatic amide;
benzimidazoles;
beta-alanine derivative;
carboxamidine;
pyridines		anticoagulant;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
EC 3.4.21.5 (thrombin) inhibitor
naringenin
(S)-naringenin : The (S)-enantiomer of naringenin.		2.110(2S)-flavan-4-one;
naringenin		expectorant;
plant metabolite
eriodictyol
eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.		2.1103'-hydroxyflavanones;
tetrahydroxyflavanone
pulegone
pulegone: component of peppermint oil; RN given refers to cpd without isomeric designation; structure in Merck. (+)-pulegone : The (5R)-enantiomer of p-menth-4(8)-en-3-one.		7.1310p-menth-4(8)-en-3-one
e-z cinnamic acid
cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid		2.420cinnamic acidplant metabolite
ferulic acid
ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.		9.09140ferulic acidsanti-inflammatory agent;
antioxidant;
apoptosis inhibitor;
cardioprotective agent;
MALDI matrix material;
plant metabolite
methyl cinnamate
methyl cinnamate: RN given refers to cpd without isomeric designation. methyl cinnamate : A methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries.. methyl trans-cinnamate : The E (trans) isomer of methyl cinnamate.		2.420methyl cinnamateantibacterial agent;
fungal metabolite;
nematicide;
plant metabolite
2-hydroxycinnamic acid
trans-2-coumaric acid : The trans-isomer of 2-coumaric acid.. 2-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring.		1.99102-coumaric acid;
phenols		antioxidant;
metabolite
3-coumaric acid
3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.		1.99103-coumaric acid
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.		2.69304-coumaric acidfood component;
mouse metabolite;
plant metabolite
glycosides
[no description available]		2.4520
benzylideneacetone
benzylideneacetone: RN given refers to cpd without isomeric; structure in Merck Index, 9th ed, #1153. trans-benzylideneacetone : The trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth.. benzylideneacetone : An enone in which a phenyl ring is attached to the beta-carbon atom of but-3-en-2-one. Although both cis- and trans-isomers are possible for the alpha,beta-unsaturated ketone, only the trans-isomer is observed.		1.9910benzylideneacetonebacterial metabolite;
EC 3.1.1.4 (phospholipase A2) inhibitor;
flavouring agent;
fragrance
chalcone
trans-chalcone : The trans-isomer of chalcone.		1.9910chalconeEC 3.2.1.1 (alpha-amylase) inhibitor
sinapinic acid
sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.		1.9910sinapic acidMALDI matrix material;
plant metabolite
2'-hydroxychalcone
2'-hydroxychalcone : A member of the class of chalcones that is trans-chalcone substituted by a hydroxy group at position 2'.		1.9910chalcones;
phenols		anti-inflammatory agent
2,2'-dihydroxychalcone
2,2'-dihydroxychalcone: an antineoplastic agent; structure in first source		1.9910
isoliquiritigenin
[no description available]		1.9910chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist
ethyl coumarate
ethyl coumarate: structure in first source		1.9910cinnamate ester
caffeic acid
trans-caffeic acid : The trans-isomer of caffeic acid.		2.4320caffeic acidgeroprotector;
mouse metabolite
methyl caffeate
methyl caffeate: from plant Gaillardia pulchella. methyl caffeate : An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.		3.4570alkyl caffeate ester;
methyl ester
ethyl ferulate
ethyl ferulate: structure in first source		3.4470
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.		2.1110guaiacols;
phenylpropanoid		animal metabolite;
monolignol;
mouse metabolite;
pheromone;
plant metabolite;
volatile oil component
cyqualon
cyclovalone: is a synthetic curcumin derivative; structure in first source		1.9910
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.		2.110coumarins;
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
tocopherylquinone
tocopherylquinone: RN refers to (3R-(3R*,7R*,11R*))-isomer; structure		2.1110
laccase
Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.		2.2510
quercetin 3-o-glucuronide
quercetin 3-O-glucuronide: structure in first source. miquelianin : A quercetin O-glycoside that consists of quercetin attached to a beta-D-glucuronopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from Salvia and Phaseolus vulgaris, it exhibits antioxidant and antidepressant activities.		2.110beta-D-glucosiduronic acid;
quercetin O-glycoside		antidepressant;
antioxidant;
metabolite
quercetin
[no description available]		2.1107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
trans-phytol
trans-phytol: structure in first source		2.1110diterpenoid;
long-chain primary fatty alcohol		algal metabolite;
plant metabolite;
schistosomicide drug
apigenin
Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.		2.110trihydroxyflavoneantineoplastic agent;
metabolite
luteolin
[no description available]		2.1103'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
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.		2.1510cinnamaldehydes;
guaiacols;
phenylpropanoid		antifungal agent;
plant metabolite
kaempferol
[no description available]		2.1107-hydroxyflavonol;
flavonols;
tetrahydroxyflavone		antibacterial agent;
geroprotector;
human blood serum metabolite;
human urinary metabolite;
human xenobiotic metabolite;
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.		1.9910hydroxycoumarinfluorescent probe;
food component;
plant metabolite
3-methylquercetin
isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.		2.1107-hydroxyflavonol;
monomethoxyflavone;
tetrahydroxyflavone		anticoagulant;
EC 1.14.18.1 (tyrosinase) inhibitor;
metabolite
3,4-di-o-caffeoylquinic acid
3,4-di-O-caffeoylquinic acid: isolated from Siphonostegia chinensis		2.1110quinic acid
astragalin
kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.		2.1110beta-D-glucoside;
kaempferol O-glucoside;
monosaccharide derivative;
trihydroxyflavone		plant metabolite;
trypanocidal drug
4-hydroxychalcone
4-hydroxychalcone: structure in first source. 4-hydroxychalcone : A member of the class of chalcones that is trans-chalcone substituted by a hydroxy group at position 4.		1.9910chalcones;
phenols		antihypertensive agent;
plant metabolite
4'-hydroxychalcone
4'-hydroxychalcone: inhibits TNFalpha-induced NF-κB activation; structure in first source. 4'-hydroxychalcone : A member of the class of chalcones that is trans-chalcone substituted by a hydroxy group at position 4'.		1.9910chalcones;
phenols		anti-inflammatory agent;
antineoplastic agent
ethyl caffeate
(E)-ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate: structure in first source. ethyl trans-caffeate : An ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol.		2.0710alkyl caffeate ester;
ethyl ester;
hydroxycinnamic acid		anti-inflammatory agent;
antineoplastic agent;
metabolite
methyl-p-coumarate
methyl-p-coumarate: structure in first source. 4-coumaric acid methyl ester : A cinnamate ester that is the methyl ester of 4-coumaric acid.		3.29604-coumaric acid methyl ester
antithiamine factor
antithiamine factor: from mustard seed; structure		2.4320hydroxycinnamic acid
4-(2-hydroxyphenyl)but-3-en-2-one
4-(2-hydroxyphenyl)but-3-en-2-one: inhibits lipopolysaccharide-induced expression of inducible nitric oxide synthase; structure in first source		1.9910
2-Phenylethyl 3-phenyl-2-propenoate
[no description available]		1.9910cinnamate ester
2,4,2'-trihydroxychalcone
2,4,2'-trihydroxychalcone: structure in first source		1.9910
ergosta-4,6,8(14),22-tetraen-3-one
ergosta-4,6,8(14),22-tetraen-3-one: antineoplastic, non-toxic fungal steroid. ergosta-4,6,8(14),22-tetraen-3-one : An ergostanoid that is (22E)-ergosta-4,6,8(14),22-tetraene substituted by an oxo group at position 3. It has been isolated from the mycelia of Cordyceps sinensis.		2.11103-oxo-Delta(4) steroid;
ergostanoid		fungal metabolite
4,5-di-O-caffeoylquinic acid
[no description available]		2.1110quinic acid
indigo carmine
3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.		2.5320
propyl caffeate
propyl caffeate: has antioxidant activity; structure in first source		2.0710
oxadiazoles
Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.		2.3110
procyanidin b1
procyanidin B1 : A proanthocyanidin consisting of (-)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8' respectively in a beta-configuration.. Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach.		2.110biflavonoid;
hydroxyflavan;
polyphenol;
proanthocyanidin		anti-inflammatory agent;
EC 3.4.21.5 (thrombin) inhibitor;
metabolite
campesteryl ferulate
campesteryl ferulate: structure in first source		2.1310steroid ester
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.		2.110benzenes;
hydroxycoumarin;
methyl ketone
ConditionIndicatedRelationship StrengthStudiesTrials
Experimental Hepatoma
[description not available]		01.9910
Glial Cell Tumors
[description not available]		02.1110
Glioma
Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)		02.1110
Acute Confusional Senile Dementia
[description not available]		02.1310
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		02.1310
Impaired Glucose Tolerance
[description not available]		02.2110
Cardiometabolic Syndrome
A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.		02.2110
Diabetes Mellitus, Adult-Onset
[description not available]		02.2110
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		02.2110
Glucose Intolerance
A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.		02.2110
Metabolic Syndrome
A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.		02.2110
Insulin Sensitivity
[description not available]		02.4110
Alcoholic Liver Diseases
[description not available]		02.6320
Insulin Resistance
Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.		02.4110
Liver Diseases, Alcoholic
Liver diseases associated with ALCOHOLISM. It usually refers to the coexistence of two or more subentities, i.e., ALCOHOLIC FATTY LIVER; ALCOHOLIC HEPATITIS; and ALCOHOLIC CIRRHOSIS.		02.6320
Acute Liver Injury, Drug-Induced
[description not available]		02.1510
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.1510
Deep Vein Thrombosis
[description not available]		02.0810
Venous Thrombosis
The formation or presence of a blood clot (THROMBUS) within a vein.		02.0810
Extravascular Hemolysis
[description not available]		02.1310
Hemolysis
The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.		02.1310