Compounds > n-cinnamoyltyramine
Page last updated: 2024-12-11

n-cinnamoyltyramine

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

Description

N-cinnamoyltyramine: isolated from Lycianthes biflora; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N-trans-cinnamoyltyramine : A member of the class of cinnamamides that is tyramine substituted by a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at the nitrogen atom. It is found in rice and exhibits an allelopathic effect to suppress the growth of weeds. [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
Lycianthesgenus[no description available]SolanaceaeA plant family of the order SOLANALES, class MAGNOLIOPSIDA. Among the most noted are POTATOES; TOMATOES; CAPSICUM (green and red peppers); TOBACCO; and BELLADONNA.[MeSH]

Cross-References

ID SourceID
PubMed CID5315911
CHEMBL ID417389
CHEBI ID177872
SCHEMBL ID22702505
MeSH IDM0456926

Synonyms (29)

Synonym
trans-cinnamoyl-p-hydroxybenzenethylamine
n-trans-cinnamoyltyramine
103188-44-9
(2e)-n-[2-(4-hydroxyphenyl)ethyl]-3-phenyl-2-propenamide
CHEBI:177872 ,
(e)-n-[2-(4-hydroxyphenyl)ethyl]-3-phenyl-2-propenamide
(2e)-n-[2-(4-hydroxyphenyl)ethyl]-3-phenylprop-2-enamide
cinnamoyltyramine
n-cinnamoyltyramine
CHEMBL417389 ,
(2e)-n-[2-(4-hydroxyphenyl)ethyl]-3-phenylacrylamide
(e)-n-[2-(4-hydroxy-phenyl)-ethyl]-3-phenyl-acrylamide
bdbm50069771
(e)-n-[2-(4-hydroxyphenyl)ethyl]-3-phenylprop-2-enamide
AKOS010246127
KGOYCHSKGXJDND-DHZHZOJOSA-N
(2e)-n-[2-(4-hydroxyphenyl)ethyl]-3-phenyl-2-propenamide #
cinnamamide, n-(p-hydroxyphenethyl)-
n-(p-hydroxyphenethyl)-3-phenylpropenamide
20384-14-9
(e)-n-(2-(4-hydroxyphenyl)ethyl)-3-phenyl-2-propenamide
(2e)-n-(2-(4-hydroxyphenyl)ethyl)-3-phenylprop-2-enamide
Z728882330
SCHEMBL22702505
CM93V4SY32 ,
(2e)-n-(2-(4-hydroxyphenyl)ethyl)-3-phenyl-2-propenamide
unii-cm93v4sy32
EN300-245816
EN300-6496383
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
phytoalexinA toxin made by a plant that acts against an organism attacking it.
antimicrobial agentA substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
platelet aggregation inhibitorA drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
allelochemicalA class of secondary metabolites developed by many plants to influence the behaviour, growth or survival of herbivores, and thus acting as a defence against herbivory.
[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
secondary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with a primary amine; formula RC(=O)NHR(1).
cinnamamidesAn enamide which is cinnamamide or a derivative of cinnamamide obtained by replacement of one or more of its hydrogens.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[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]

Pathways (1)

PathwayProteinsCompounds
hydroxycinnamic acid tyramine amides biosynthesis021

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)IC50 (µMol)66.89330.00071.600310.0000AID143779; AID143785; AID143788
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.630610.0000AID143779
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC50 (µMol)0.68000.00061.525710.0000AID143785
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.747210.0000AID143788
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID143374Antagonistic activity towards NMDA receptor 1A/2B subtype was determined1998Bioorganic & medicinal chemistry letters, Jan-20, Volume: 8, Issue:2
N-(2-(4-hydroxyphenyl)ethyl)-4-chlorocinnamide: a novel antagonist at the 1A/2B NMDA receptor subtype.
AID143779Antagonistic activity against N-methyl-D-aspartate glutamate receptor 1/2A.1999Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17
Structure-activity relationship of N-(phenylalkyl)cinnamides as novel NR2B subtype-selective NMDA receptor antagonists.
AID1293688Inhibition of baker's yeast alpha-glucosidase using pNPG as substrate by spectrophotometry2016European journal of medicinal chemistry, May-23, Volume: 114Cinnamic acid amides from Tribulus terrestris displaying uncompetitive α-glucosidase inhibition.
AID143258Antagonistic activity towards NMDA receptor 1A/2A subtype was determined1998Bioorganic & medicinal chemistry letters, Jan-20, Volume: 8, Issue:2
N-(2-(4-hydroxyphenyl)ethyl)-4-chlorocinnamide: a novel antagonist at the 1A/2B NMDA receptor subtype.
AID143375Antagonistic activity towards NMDA receptor 1A/2C subtype was determined1998Bioorganic & medicinal chemistry letters, Jan-20, Volume: 8, Issue:2
N-(2-(4-hydroxyphenyl)ethyl)-4-chlorocinnamide: a novel antagonist at the 1A/2B NMDA receptor subtype.
AID143788Antagonistic activity against N-methyl-D-aspartate glutamate receptor 1/2C.1999Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17
Structure-activity relationship of N-(phenylalkyl)cinnamides as novel NR2B subtype-selective NMDA receptor antagonists.
AID1293689Uncompetitive inhibition of baker's yeast alpha-glucosidase using pNPG as substrate by Cornish-Bowden plot analysis2016European journal of medicinal chemistry, May-23, Volume: 114Cinnamic acid amides from Tribulus terrestris displaying uncompetitive α-glucosidase inhibition.
AID143785Antagonistic activity against N-methyl-D-aspartate glutamate receptor 1/2B.1999Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17
Structure-activity relationship of N-(phenylalkyl)cinnamides as novel NR2B subtype-selective NMDA receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (28.57)18.2507
2000's1 (14.29)29.6817
2010's3 (42.86)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.86

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 Index12.86 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.94 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
4-hydroxybenzaldehyde
[no description available]		2.1310hydroxybenzaldehydeEC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor;
mouse metabolite;
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.		2.1310guaiacolsdisinfectant;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
expectorant;
plant metabolite
phenethylamine
phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.		2.110alkaloid;
aralkylamine;
phenylethylamine		Escherichia coli metabolite;
human metabolite;
mouse metabolite
tyramine
[no description available]		4.140monoamine molecular messenger;
primary amino compound;
tyramines		EC 3.1.1.8 (cholinesterase) inhibitor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter
4-butyrolactone
4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.		2.0110butan-4-olidemetabolite;
neurotoxin
phloretic acid
phloretic acid: structure. N-hydroxysuccinimide ester : An ester of N-hydroxysuccinimide.. phloretic acid : A hydroxy monocarboxylic acid consisting of propionic acid having a 4-hydroxyphenyl group at the 3-position.		2.1310hydroxy monocarboxylic acidplant metabolite
1-deoxynojirimycin
1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.		2.13102-(hydroxymethyl)piperidine-3,4,5-triol;
piperidine alkaloid		anti-HIV agent;
anti-obesity agent;
bacterial metabolite;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
hepatoprotective agent;
hypoglycemic agent;
plant metabolite
syringaresinol
[no description available]		2.1310aromatic ether;
furofuran;
lignan;
polyether;
polyphenol		plant metabolite
cp 101,606
traxoprodil mesylate: a selective NMDA antagonist; structure given in first source		210
lignans
Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)		2.1310
gamma-sitosterol
clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.		2.13103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
phytosterols		marine metabolite;
plant metabolite
cytellin
cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982		2.1310
gigantol
gigantol: structure in first source		2.1310
feruloyltyramine
feruloyltyramine: structure given in first source; isolated from Cannabis sativa seeds, roots, leaves, and resin; induces hypothermia and motor incoordination in mice; moupinamide is (E)-isomer		2.5320tyraminesmetabolite
tyrphostin ag 555
[no description available]		210
tyrphostin ag-494
AG 494: tyrphostin that blocks Cdk2 activation; structure in first source		210
ag 556
AG 556: structure given in first source		210
ag-490
[no description available]		210catechols;
enamide;
monocarboxylic acid amide;
nitrile;
secondary carboxamide		anti-inflammatory agent;
antioxidant;
apoptosis inducer;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
geroprotector;
STAT3 inhibitor
n-(4-hydroxy-beta-phenethyl)-4-hydroxycinnamide
trans-N-p-coumaroyl tyramine: from the twigs of Celtis chinensis; structure in first source		2.7130hydroxycinnamic acidmetabolite
ro 25-6981
Ro 25-6981: blocks NMDA receptors containg NR2B subunit; structure in first source. Ro 25-6981 : A member of the class of piperidines that is 4-benzylpiperidine substituted by a 3-hydroxy-3-(4-hydroxyphenyl)-2-methylpropyl group at position 1 (the 1R,2S-stereoisomer). It is a potent antagonist of the GluN2B subunit of the N-methyl-D-aspartate (NMDA) receptor.		210benzenes;
phenols;
piperidines;
secondary alcohol;
tertiary amino compound		anticonvulsant;
antidepressant;
neuroprotective agent;
NMDA receptor antagonist
n-caffeoyltyramine
N-caffeoyltyramine: structure in first source		2.1310catechols
n-coumaroyldopamine
N-coumaroyldopamine: structure in first source		2.1310
n-trans-feruloyloctopamine
N-feruloyloctopamine: has antifungal activity; isolated from root bark of Lycium chinense; structure in first source		2.1310methoxybenzenes;
phenols
phenanthrenes
Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.		2.1310
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		02.0110