Page last updated: 2024-11-12

n-caffeoyldopamine

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Description

N-caffeoyldopamine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10171904
CHEMBL ID68132
SCHEMBL ID109066
MeSH IDM0492854

Synonyms (28)

Synonym
(e)-3-(3,4-dihydroxyphenyl)-n-[2-(3,4-dihydroxyphenyl)ethyl]prop-2-enamide
CHEMBL68132 ,
103188-49-4
AKOS016012370
SCHEMBL109066
(e)-n-(3,4-dihydroxyphenethyl)-3-(3,4-dihydroxyphenyl)acrylamide
AC-26418
(2e)-3-(3,4-dihydroxyphenyl)-n-[2-(3,4-dihydroxyphenyl)ethyl]prop-2-enamide
3-(3,4-dihydroxyphenyl)-n-[2-(3,4-dihydroxyphenyl)ethyl]prop-2-enamide
n-(3,4-dihydroxyphenethyl)-3-(3,4-dihydroxyphenyl)acrylamide
caffeoyldopamine
(e)-3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-2-propenamide
105955-00-8
2-propenamide, 3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-
caffedymine
n-caffeoyldopamine
HEM1G2VY70 ,
unii-hem1g2vy70
(2e)-3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-2-propenamide
2-propenamide, 3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-, (2e)-
bdbm50276918
BS-14192
AMY3760
A896592
C14041
CS-0186103
p-coumaric acid derivative 2
Z1625563034
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Amyloid-beta precursor proteinHomo sapiens (human)EC50 (µMol)69.00000.00074.20538.4100AID1500513
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (79)

Processvia Protein(s)Taxonomy
regulation of gene expressionAmyloid-beta precursor proteinHomo sapiens (human)
cognitionAmyloid-beta precursor proteinHomo sapiens (human)
G2/M transition of mitotic cell cycleAmyloid-beta precursor proteinHomo sapiens (human)
microglial cell activationAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of protein phosphorylationAmyloid-beta precursor proteinHomo sapiens (human)
suckling behaviorAmyloid-beta precursor proteinHomo sapiens (human)
astrocyte activation involved in immune responseAmyloid-beta precursor proteinHomo sapiens (human)
regulation of translationAmyloid-beta precursor proteinHomo sapiens (human)
protein phosphorylationAmyloid-beta precursor proteinHomo sapiens (human)
intracellular copper ion homeostasisAmyloid-beta precursor proteinHomo sapiens (human)
endocytosisAmyloid-beta precursor proteinHomo sapiens (human)
response to oxidative stressAmyloid-beta precursor proteinHomo sapiens (human)
cell adhesionAmyloid-beta precursor proteinHomo sapiens (human)
regulation of epidermal growth factor-activated receptor activityAmyloid-beta precursor proteinHomo sapiens (human)
Notch signaling pathwayAmyloid-beta precursor proteinHomo sapiens (human)
axonogenesisAmyloid-beta precursor proteinHomo sapiens (human)
learning or memoryAmyloid-beta precursor proteinHomo sapiens (human)
learningAmyloid-beta precursor proteinHomo sapiens (human)
mating behaviorAmyloid-beta precursor proteinHomo sapiens (human)
locomotory behaviorAmyloid-beta precursor proteinHomo sapiens (human)
axo-dendritic transportAmyloid-beta precursor proteinHomo sapiens (human)
cholesterol metabolic processAmyloid-beta precursor proteinHomo sapiens (human)
negative regulation of cell population proliferationAmyloid-beta precursor proteinHomo sapiens (human)
adult locomotory behaviorAmyloid-beta precursor proteinHomo sapiens (human)
visual learningAmyloid-beta precursor proteinHomo sapiens (human)
regulation of gene expressionAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of gene expressionAmyloid-beta precursor proteinHomo sapiens (human)
negative regulation of gene expressionAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of peptidyl-threonine phosphorylationAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of G2/M transition of mitotic cell cycleAmyloid-beta precursor proteinHomo sapiens (human)
microglia developmentAmyloid-beta precursor proteinHomo sapiens (human)
axon midline choice point recognitionAmyloid-beta precursor proteinHomo sapiens (human)
neuron remodelingAmyloid-beta precursor proteinHomo sapiens (human)
dendrite developmentAmyloid-beta precursor proteinHomo sapiens (human)
regulation of Wnt signaling pathwayAmyloid-beta precursor proteinHomo sapiens (human)
extracellular matrix organizationAmyloid-beta precursor proteinHomo sapiens (human)
forebrain developmentAmyloid-beta precursor proteinHomo sapiens (human)
neuron projection developmentAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of chemokine productionAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of interleukin-1 beta productionAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of interleukin-6 productionAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of tumor necrosis factor productionAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationAmyloid-beta precursor proteinHomo sapiens (human)
ionotropic glutamate receptor signaling pathwayAmyloid-beta precursor proteinHomo sapiens (human)
regulation of multicellular organism growthAmyloid-beta precursor proteinHomo sapiens (human)
negative regulation of neuron differentiationAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of glycolytic processAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of mitotic cell cycleAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of JNK cascadeAmyloid-beta precursor proteinHomo sapiens (human)
astrocyte activationAmyloid-beta precursor proteinHomo sapiens (human)
regulation of long-term neuronal synaptic plasticityAmyloid-beta precursor proteinHomo sapiens (human)
collateral sprouting in absence of injuryAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of inflammatory responseAmyloid-beta precursor proteinHomo sapiens (human)
regulation of peptidyl-tyrosine phosphorylationAmyloid-beta precursor proteinHomo sapiens (human)
regulation of synapse structure or activityAmyloid-beta precursor proteinHomo sapiens (human)
synapse organizationAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of calcium-mediated signalingAmyloid-beta precursor proteinHomo sapiens (human)
neuromuscular process controlling balanceAmyloid-beta precursor proteinHomo sapiens (human)
synaptic assembly at neuromuscular junctionAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of protein metabolic processAmyloid-beta precursor proteinHomo sapiens (human)
neuron apoptotic processAmyloid-beta precursor proteinHomo sapiens (human)
smooth endoplasmic reticulum calcium ion homeostasisAmyloid-beta precursor proteinHomo sapiens (human)
neuron cellular homeostasisAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeAmyloid-beta precursor proteinHomo sapiens (human)
response to interleukin-1Amyloid-beta precursor proteinHomo sapiens (human)
modulation of excitatory postsynaptic potentialAmyloid-beta precursor proteinHomo sapiens (human)
NMDA selective glutamate receptor signaling pathwayAmyloid-beta precursor proteinHomo sapiens (human)
regulation of spontaneous synaptic transmissionAmyloid-beta precursor proteinHomo sapiens (human)
cytosolic mRNA polyadenylationAmyloid-beta precursor proteinHomo sapiens (human)
negative regulation of long-term synaptic potentiationAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of long-term synaptic potentiationAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of non-canonical NF-kappaB signal transductionAmyloid-beta precursor proteinHomo sapiens (human)
cellular response to amyloid-betaAmyloid-beta precursor proteinHomo sapiens (human)
regulation of presynapse assemblyAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of amyloid fibril formationAmyloid-beta precursor proteinHomo sapiens (human)
amyloid fibril formationAmyloid-beta precursor proteinHomo sapiens (human)
neuron projection maintenanceAmyloid-beta precursor proteinHomo sapiens (human)
positive regulation of T cell migrationAmyloid-beta precursor proteinHomo sapiens (human)
central nervous system developmentAmyloid-beta precursor proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingAmyloid-beta precursor proteinHomo sapiens (human)
DNA bindingAmyloid-beta precursor proteinHomo sapiens (human)
serine-type endopeptidase inhibitor activityAmyloid-beta precursor proteinHomo sapiens (human)
signaling receptor bindingAmyloid-beta precursor proteinHomo sapiens (human)
protein bindingAmyloid-beta precursor proteinHomo sapiens (human)
heparin bindingAmyloid-beta precursor proteinHomo sapiens (human)
enzyme bindingAmyloid-beta precursor proteinHomo sapiens (human)
identical protein bindingAmyloid-beta precursor proteinHomo sapiens (human)
transition metal ion bindingAmyloid-beta precursor proteinHomo sapiens (human)
receptor ligand activityAmyloid-beta precursor proteinHomo sapiens (human)
PTB domain bindingAmyloid-beta precursor proteinHomo sapiens (human)
protein serine/threonine kinase bindingAmyloid-beta precursor proteinHomo sapiens (human)
signaling receptor activator activityAmyloid-beta precursor proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (41)

Processvia Protein(s)Taxonomy
extracellular spaceAmyloid-beta precursor proteinHomo sapiens (human)
dendriteAmyloid-beta precursor proteinHomo sapiens (human)
extracellular regionAmyloid-beta precursor proteinHomo sapiens (human)
extracellular spaceAmyloid-beta precursor proteinHomo sapiens (human)
nuclear envelope lumenAmyloid-beta precursor proteinHomo sapiens (human)
cytoplasmAmyloid-beta precursor proteinHomo sapiens (human)
mitochondrial inner membraneAmyloid-beta precursor proteinHomo sapiens (human)
endosomeAmyloid-beta precursor proteinHomo sapiens (human)
early endosomeAmyloid-beta precursor proteinHomo sapiens (human)
endoplasmic reticulumAmyloid-beta precursor proteinHomo sapiens (human)
endoplasmic reticulum lumenAmyloid-beta precursor proteinHomo sapiens (human)
smooth endoplasmic reticulumAmyloid-beta precursor proteinHomo sapiens (human)
Golgi apparatusAmyloid-beta precursor proteinHomo sapiens (human)
Golgi lumenAmyloid-beta precursor proteinHomo sapiens (human)
Golgi-associated vesicleAmyloid-beta precursor proteinHomo sapiens (human)
cytosolAmyloid-beta precursor proteinHomo sapiens (human)
plasma membraneAmyloid-beta precursor proteinHomo sapiens (human)
clathrin-coated pitAmyloid-beta precursor proteinHomo sapiens (human)
cell-cell junctionAmyloid-beta precursor proteinHomo sapiens (human)
synaptic vesicleAmyloid-beta precursor proteinHomo sapiens (human)
cell surfaceAmyloid-beta precursor proteinHomo sapiens (human)
membraneAmyloid-beta precursor proteinHomo sapiens (human)
COPII-coated ER to Golgi transport vesicleAmyloid-beta precursor proteinHomo sapiens (human)
axonAmyloid-beta precursor proteinHomo sapiens (human)
growth coneAmyloid-beta precursor proteinHomo sapiens (human)
platelet alpha granule lumenAmyloid-beta precursor proteinHomo sapiens (human)
neuromuscular junctionAmyloid-beta precursor proteinHomo sapiens (human)
endosome lumenAmyloid-beta precursor proteinHomo sapiens (human)
trans-Golgi network membraneAmyloid-beta precursor proteinHomo sapiens (human)
ciliary rootletAmyloid-beta precursor proteinHomo sapiens (human)
dendritic spineAmyloid-beta precursor proteinHomo sapiens (human)
dendritic shaftAmyloid-beta precursor proteinHomo sapiens (human)
perikaryonAmyloid-beta precursor proteinHomo sapiens (human)
membrane raftAmyloid-beta precursor proteinHomo sapiens (human)
apical part of cellAmyloid-beta precursor proteinHomo sapiens (human)
synapseAmyloid-beta precursor proteinHomo sapiens (human)
perinuclear region of cytoplasmAmyloid-beta precursor proteinHomo sapiens (human)
presynaptic active zoneAmyloid-beta precursor proteinHomo sapiens (human)
spindle midzoneAmyloid-beta precursor proteinHomo sapiens (human)
recycling endosomeAmyloid-beta precursor proteinHomo sapiens (human)
extracellular exosomeAmyloid-beta precursor proteinHomo sapiens (human)
receptor complexAmyloid-beta precursor proteinHomo sapiens (human)
early endosomeAmyloid-beta precursor proteinHomo sapiens (human)
membrane raftAmyloid-beta precursor proteinHomo sapiens (human)
cell surfaceAmyloid-beta precursor proteinHomo sapiens (human)
Golgi apparatusAmyloid-beta precursor proteinHomo sapiens (human)
plasma membraneAmyloid-beta precursor proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID1253010Protective activity against isoniazid and rifampicin-induced hepatotoxicity in Wistar rat assessed as reduction of MDA level at 2.5 mg/kg, po (Rvb = 30.5 +/- 7.8 nM/mg)2015Bioorganic & medicinal chemistry letters, Nov-15, Volume: 25, Issue:22
Protective effects of the bioactive natural product N-trans-Caffeoyldopamine on hepatotoxicity induced by isoniazid and rifampicin.
AID1253013Protective activity against isoniazid and rifampicin-induced hepatotoxicity in Wistar rat assessed as decrease of CYP2E1 mRNA expression in liver2015Bioorganic & medicinal chemistry letters, Nov-15, Volume: 25, Issue:22
Protective effects of the bioactive natural product N-trans-Caffeoyldopamine on hepatotoxicity induced by isoniazid and rifampicin.
AID263691DPPH radical scavenging activity at 100 uM2006Bioorganic & medicinal chemistry letters, Apr-15, Volume: 16, Issue:8
Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase.
AID1253011Protective activity against isoniazid and rifampicin-induced hepatotoxicity in Wistar rat assessed as increase of GSH activity at 2.5 mg/kg, po (Rvb = 29.4 +/- 11.4 uM/gram)2015Bioorganic & medicinal chemistry letters, Nov-15, Volume: 25, Issue:22
Protective effects of the bioactive natural product N-trans-Caffeoyldopamine on hepatotoxicity induced by isoniazid and rifampicin.
AID1500522Inhibition of butter milk XOD (unknown origin) at 100 uM using xanthine as substrate after 8 mins relative to control2017European journal of medicinal chemistry, Sep-29, Volume: 138Structure-activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties.
AID306326Antimicrobial activity against fluoroquinolone-resistant Staphylococcus aureus SA1199B2007Bioorganic & medicinal chemistry letters, Mar-15, Volume: 17, Issue:6
N-caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors.
AID306328Inhibition of NorA pump in fluoroquinolone-resistant Staphylococcus aureus SA1199B assessed as drug level causing 4-fold reduction of Norfloxacin MIC2007Bioorganic & medicinal chemistry letters, Mar-15, Volume: 17, Issue:6
N-caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors.
AID1500523Antioxidant activity assessed as inhibition of DPPH radical at 100 uM incubated for 20 mins measured for 60 mins relative to control2017European journal of medicinal chemistry, Sep-29, Volume: 138Structure-activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties.
AID125798Evaluated for the antioxidant property by measuring the inhibition of microsomal lipid peroxidation2001Bioorganic & medicinal chemistry letters, Jan-22, Volume: 11, Issue:2
Synthesis and evaluation of caffeic acid amides as antioxidants.
AID1253012Protective activity against isoniazid and rifampicin-induced hepatotoxicity in Wistar rat by haematoxylin and eosin staining2015Bioorganic & medicinal chemistry letters, Nov-15, Volume: 25, Issue:22
Protective effects of the bioactive natural product N-trans-Caffeoyldopamine on hepatotoxicity induced by isoniazid and rifampicin.
AID263688Inhibitory activity against tyrosinase at 100uM2006Bioorganic & medicinal chemistry letters, Apr-15, Volume: 16, Issue:8
Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase.
AID1500513Inhibition of QD-labeled amyloid beta (1 to 42) (unknown origin) aggregation after 24 hrs by inverted fluorescence microscopic method2017European journal of medicinal chemistry, Sep-29, Volume: 138Structure-activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties.
AID1500524Antioxidant activity assessed as inhibition of DPPH radical at 500 uM incubated for 20 mins measured for 60 mins relative to control2017European journal of medicinal chemistry, Sep-29, Volume: 138Structure-activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties.
AID1500521Inhibition of butter milk XOD (unknown origin) at 10 uM using xanthine as substrate after 8 mins relative to control2017European journal of medicinal chemistry, Sep-29, Volume: 138Structure-activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties.
AID1253007Protective activity against isoniazid and rifampicin-induced hepatotoxicity in Wistar rat assessed as reduction of serum ALT level at 2.5 mg/kg, po (Rvb = 143.7 +/- 12.5 U)2015Bioorganic & medicinal chemistry letters, Nov-15, Volume: 25, Issue:22
Protective effects of the bioactive natural product N-trans-Caffeoyldopamine on hepatotoxicity induced by isoniazid and rifampicin.
AID1253008Protective activity against isoniazid and rifampicin-induced hepatotoxicity in Wistar rat assessed as reduction of serum AST level at 2.5 mg/kg, po (Rvb = 168.5 +/- 14.7 U)2015Bioorganic & medicinal chemistry letters, Nov-15, Volume: 25, Issue:22
Protective effects of the bioactive natural product N-trans-Caffeoyldopamine on hepatotoxicity induced by isoniazid and rifampicin.
AID1253009Protective activity against isoniazid and rifampicin-induced hepatotoxicity in Wistar rat assessed as increase of SOD activity at 2.5 mg/kg, po (Rvb = 31.4 +/- 8.3 U/mg)2015Bioorganic & medicinal chemistry letters, Nov-15, Volume: 25, Issue:22
Protective effects of the bioactive natural product N-trans-Caffeoyldopamine on hepatotoxicity induced by isoniazid and rifampicin.
AID306327Inhibition of NorA pump in fluoroquinolone-resistant Staphylococcus aureus SA1199B assessed as drug level causing 8-fold reduction of Norfloxacin MIC2007Bioorganic & medicinal chemistry letters, Mar-15, Volume: 17, Issue:6
N-caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's7 (77.78)29.6817
2010's2 (22.22)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.59

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 Index22.59 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.59)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]