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n-(p-coumaroyl)serotonin

Description

N-(p-coumaroyl)serotonin: structure in first source [MeSH]

N6-cis-p-Coumaroylserotonin : no description available [CHeBI]

Cross-References

ID SourceID
PubMed CID5458879
CHEMBL ID1760547
SCHEMBL ID471921
CHEBI ID175113
MeSH IDM0295845

Synonyms (42)

Synonym
(e)-n-[2-(5-hydroxy-1h-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
201301-83-9
n6-cis-p-coumaroylserotonin
CHEBI:175113
5-hydroxy-n-feruloyltryptamine
serotonin ii, n (p-coumaroyl)-
nsc-369503
tryptamine, 5-hydroxy-n-
NSC369503 ,
68573-24-0
p-coumaric acid serotonin amide
p-coumaroylserotonin
CHEMBL1760547 ,
n-p-coumaroyl serotonin
bdbm50341135
unii-iuc27q8ach
2-propenamide, n-(2-(5-hydroxy-1h-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)-, (2e)-
iuc27q8ach ,
coumaroylserotonin 98
n-coumaroyl serotonin
p-c-serotonin
4-coumaroylserotonin
2-propenamide, n-(2-(5-hydroxy-1h-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)-, (e)-
trans-n-(p-coumaroyl)serotonin
n-coumaroyl serotonin [inci]
n-[2-(5-hydroxy-1h-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)-2-propenamide
n-(p-coumaroyl) serotonin
nsc 369503
(e)-n-(2-(5-hydroxy-1h-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide
WLZPAFGVOWCVMG-FPYGCLRLSA-N
SCHEMBL471921
DTXSID10173951
(2e)-n-[2-(5-hydroxy-1h-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
n-(p-coumaroyl)serotonin
n-[2-(5-hydroxy-1h-indol-3-yl)ethyl]-p-coumaramide
Q27280901
n-(2-(5-hydroxy-1h-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide
HY-129440
n-(p-oumaroyl) serotonin
AS-81895
CS-0105540
Z3247251374

Drug Classes (2)

ClassDescription
hydroxyindolesAny member of the class of indoles carrying at least one hydroxy group.
carboxamideAn amide of a carboxylic acid, having the structure RC(=O)NR2. The term is used as a suffix in systematic name formation to denote the -C(=O)NH2 group including its carbon atom.

Pathways (1)

n-(p-coumaroyl)serotonin is involved in 1 pathway(s), involving a total of 0 unique proteins and 34 unique compounds

PathwayProteinsCompounds
hydroxycinnamic acid serotonin amides biosynthesis017

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Polyphenol oxidase 2Agaricus bisporusIC508.8000AID590195

Activation Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Amine oxidase [flavin-containing] BHomo sapiens (human)EC501.2000AID1564246

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1367568Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production measured after 24 hrs by Griess assay2017Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23
ISSN: 1464-3405
Inhibitory effect of moschamine isolated from Carthamus tinctorius on LPS-induced inflammatory mediators via AP-1 and STAT1/3 inactivation in RAW 264.7 macrophages.
AID590194Antioxidant activity assessed as DPPH radical scavenging activity by spectrophotometry2011Bioorganic & medicinal chemistry letters, Apr-01, Volume: 21, Issue:7
ISSN: 1464-3405
Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition.
AID1367569Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability up to 200 uM measured after 24 hrs in presence of LPS by MTT assay2017Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23
ISSN: 1464-3405
Inhibitory effect of moschamine isolated from Carthamus tinctorius on LPS-induced inflammatory mediators via AP-1 and STAT1/3 inactivation in RAW 264.7 macrophages.
AID652653Inhibition of COX2 at 400 uM after 5 mins by spectrophotometric analysis2012Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7
ISSN: 1464-3405
N-Caffeoyl serotonin as selective COX-2 inhibitor.
AID652652Inhibition of COX1 at 400 uM after 5 mins by spectrophotometric analysis2012Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7
ISSN: 1464-3405
N-Caffeoyl serotonin as selective COX-2 inhibitor.
AID590195Inhibition of mushroom tyrosinase after 25 mins by spectrophotometry2011Bioorganic & medicinal chemistry letters, Apr-01, Volume: 21, Issue:7
ISSN: 1464-3405
Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition.
AID1367591Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability up to 200 uM measured after 24 hrs in absence of LPS by MTT assay2017Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23
ISSN: 1464-3405
Inhibitory effect of moschamine isolated from Carthamus tinctorius on LPS-induced inflammatory mediators via AP-1 and STAT1/3 inactivation in RAW 264.7 macrophages.
AID1564246Inhibition of recombinant human MAOB using kynuramine as substrate preincubated with substrate for 10 mins followed by enzyme addition and measured after 20 mins by fluorescence spectrophotometry2019European journal of medicinal chemistry, Nov-01, Volume: 181ISSN: 1768-3254Cinnamamide: An insight into the pharmacological advances and structure-activity relationships.
AID1367567Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced PGE2 production pretreated for 1 hr followed by LPS addition measured after 24 hrs2017Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23
ISSN: 1464-3405
Inhibitory effect of moschamine isolated from Carthamus tinctorius on LPS-induced inflammatory mediators via AP-1 and STAT1/3 inactivation in RAW 264.7 macrophages.

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (9.52)18.2507
2000's7 (33.33)29.6817
2010's12 (57.14)24.3611
2020's0 (0.00)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (90.91%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
3-(1-methyl-4-piperidinyl)-1H-indol-5-olhydroxyindoles00low000000
psilocinhydroxyindoles;
phenols;
tertiary amino compound;
tryptamine alkaloid
drug metabolite;
fungal metabolite;
hallucinogen;
human xenobiotic metabolite;
serotonergic agonist
00low000000
3-hydroxy-2-oxoindolehydroxyindoles;
oxindoles
00low000000
indigohydroxyindoles00low000000
5-hydroxyindolehydroxyindoleshuman metabolite00low000000
indoxylheteroaryl hydroxy compound;
hydroxyindoles
00low000000
hydroxyindoleacetaldehydehydroxyindoles;
indoleacetaldehyde
human metabolite;
mouse metabolite
00low000000
4-hydroxyindolehydroxyindoles;
phenols
00low000000
3-hydroxy-3-methyloxindolehydroxyindoles;
methylindole;
oxindoles
00low000000
N-(2-hydroxy-5-methoxy-1H-indol-3-yl)acetamidehydroxyindoles00low000000
N-(1,3-benzodioxol-5-yl)-2-[(8-methoxy-5H-[1,2,4]triazino[5,6-b]indol-3-yl)thio]acetamidehydroxyindoles00low000000
n-feruloylserotoninaromatic ether;
cinnamamides;
hydroxyindoles;
phenols;
secondary carboxamide
plant metabolite00low000000
2-(8-methoxy-4-methyl-1-oxo-[1,2,4]triazino[4,5-a]indol-2-yl)-N-(3-propan-2-yloxypropyl)acetamidehydroxyindoles00low000000
n-(2-(5-methoxy-2-oxo-2,3-dihydro-1h-indol-3-yl)ethyl)acetamideacetamides;
hydroxyindoles;
tryptamines
antineoplastic agent;
apoptosis inducer;
plant metabolite
00low000000
2-hydroxy-3-(5-((morpholin-4-yl)methyl)pyridin-2-yl)-1h-indole-5-carbonitrilehydroxyindoles;
morpholines;
nitrile;
pyridines;
tertiary amino compound
antineoplastic agent;
apoptosis inducer;
EC 2.7.11.26 (tau-protein kinase) inhibitor;
tau aggregation inhibitor
00low000000
pp242aromatic amine;
biaryl;
hydroxyindoles;
phenols;
primary amino compound;
pyrazolopyrimidine
antineoplastic agent;
mTOR inhibitor
00low000000
chloramphenicolC-nitro compound;
carboxamide;
diol;
organochlorine compound
antibacterial drug;
antimicrobial agent;
Escherichia coli metabolite;
geroprotector;
Mycoplasma genitalium metabolite;
protein synthesis inhibitor
00low000000
n,n-diethylformamidecarboxamide00low000000
amikacinalpha-D-glucoside;
amino cyclitol glycoside;
aminoglycoside;
carboxamide
antibacterial drug;
antimicrobial agent;
nephrotoxin
00low000000
furalaxylalanine derivative;
aromatic amide;
carboxamide;
furans;
methyl ester
00low000000
metalaxylalanine derivative;
aromatic amide;
carboxamide;
ether;
methyl ester
00low000000
benalaxylalanine derivative;
aromatic amide;
carboxamide;
methyl ester
00low000000
10-hydroxycarbamazepinecarboxamide;
dibenzoazepine;
ureas
anticonvulsant;
drug allergen;
sodium channel blocker
00low000000
5-hydroxypyrazinamidecarboxamide;
pyrazines
00low000000
eslicarbazepine acetateacetate ester;
carboxamide;
dibenzoazepine;
ureas
anticonvulsant;
drug allergen
00low000000
ritonavir1,3-thiazoles;
carbamate ester;
carboxamide;
L-valine derivative;
ureas
antiviral drug;
environmental contaminant;
HIV protease inhibitor;
xenobiotic
00low000000
ximelagatranamidoxime;
azetidines;
carboxamide;
ethyl ester;
hydroxylamines;
secondary amino compound;
secondary carboxamide;
tertiary carboxamide
anticoagulant;
EC 3.4.21.5 (thrombin) inhibitor;
prodrug;
serine protease inhibitor
00low000000
cilastatincarboxamide;
L-cysteine derivative;
non-proteinogenic L-alpha-amino acid;
organic sulfide
EC 3.4.13.19 (membrane dipeptidase) inhibitor;
environmental contaminant;
protease inhibitor;
xenobiotic
00low000000
n-stearoyl-dopaminecarboxamide00low000000
eliglustatbenzodioxine;
carboxamide;
N-alkylpyrrolidine;
secondary alcohol
EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor00low000000
bms-790052biphenyls;
carbamate ester;
carboxamide;
imidazoles;
valine derivative
antiviral drug;
nonstructural protein 5A inhibitor
00low000000
AZD1979aromatic ether;
azaspiro compound;
carboxamide;
N-acylazetidine;
oxadiazole;
oxaspiro compound;
oxetanes
melanin-concentrating hormone receptor antagonist00low000000
ledipasvirazaspiro compound;
benzimidazole;
bridged compound;
carbamate ester;
carboxamide;
fluorenes;
imidazoles;
L-valine derivative;
N-acylpyrrolidine;
organofluorine compound
antiviral drug;
hepatitis C protease inhibitor
00low000000
chrysopineamino acid opine;
carboxamide;
delta-lactone;
secondary amino compound;
spiroketal;
triol
plant metabolite00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
aspirinbenzoic acids;
phenyl acetates;
salicylates
anticoagulant;
antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
plant activator;
platelet aggregation inhibitor;
prostaglandin antagonist;
teratogenic agent
2012201212.0low000010
kojic acid4-pyranones;
enol;
primary alcohol
Aspergillus metabolite;
EC 1.10.3.1 (catechol oxidase) inhibitor;
EC 1.10.3.2 (laccase) inhibitor;
EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor;
EC 1.14.18.1 (tyrosinase) inhibitor;
EC 1.4.3.3 (D-amino-acid oxidase) inhibitor;
NF-kappaB inhibitor;
skin lightening agent
2011201113.0low000010
n-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamidearomatic ether;
C-nitro compound;
sulfonamide
antineoplastic agent;
cyclooxygenase 2 inhibitor
201720177.0low000010
butylated hydroxytoluenephenolsantioxidant;
ferroptosis inhibitor;
food additive;
geroprotector
2011201113.0low000010
secoisolariciresinolsecoisolariciresinolantidepressant;
phytoestrogen;
plant metabolite
201720177.0low000010
trachelosideglycoside;
lignan
metabolite201720177.0medium000010
arbutinbeta-D-glucoside;
monosaccharide derivative
Escherichia coli metabolite;
plant metabolite
2011201113.0low000010
e-z cinnamic acidcinnamic acidplant metabolite2011201113.0low000010
ferulic acidferulic acidsanti-inflammatory agent;
antioxidant;
apoptosis inhibitor;
cardioprotective agent;
MALDI matrix material;
plant metabolite
2011201113.0low000010
trans-4-coumaric acid4-coumaric acidfood component;
mouse metabolite;
plant metabolite
2011201113.0low000010
sinapinic acidsinapic acidMALDI matrix material;
plant metabolite
2011201212.5low000020
caffeic acidcaffeic acidgeroprotector;
mouse metabolite
2011201212.5low000020
4-methoxycinnamic acidcinnamic acids2011201113.0low000010
3-(3,4-dimethoxyphenyl)propenoic acidmethoxycinnamic acid2011201113.0low000010
isoferulic acidferulic acidsantioxidant;
biomarker;
metabolite
2011201113.0low000010
n(6)-(1-iminoethyl)lysineL-lysine derivative;
non-proteinogenic L-alpha-amino acid
201720177.0low000010
n-feruloylserotoninaromatic ether;
cinnamamides;
hydroxyindoles;
phenols;
secondary carboxamide
plant metabolite2011201710.7medium000030
a 286982201920195.0medium000010
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
methanolalkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound
amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
2011201113.0low000010
potassium chlorideinorganic chloride;
inorganic potassium salt;
potassium salt
fertilizer2011201113.0low000010
tyraminemonoamine molecular messenger;
primary amino compound;
tyramines
EC 3.1.1.8 (cholinesterase) inhibitor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter
2004200818.0low000200
magnoflorineaporphine alkaloid;
quaternary ammonium ion
plant metabolite201820186.0low000010
chalconechalconeEC 3.2.1.1 (alpha-amylase) inhibitor201620168.0low000010
feruloyltyraminetyraminesmetabolite2004200818.0low000200
n-feruloylserotoninaromatic ether;
cinnamamides;
hydroxyindoles;
phenols;
secondary carboxamide
plant metabolite2006201613.1high000440
hydroxysafflor yellow a201620168.0low000010
cardiovascular agents201620168.0low000010
epidermal growth factor1999199925.0low001000
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Astrocytoma, Grade IV0201720177.0low000010
Atherogenesis02006200916.5medium000200
Atherosclerosis02006200916.5medium000200
Benign Neoplasms, Brain0201720177.0low000010
Body Weight02009200915.0low000100
Brain Neoplasms0201720177.0low000010
Elevated Cholesterol02009200915.0low000100
Glioblastoma0201720177.0low000010
Hypercholesterolemia02009200915.0low000100
Muscle Contraction02011201113.0low000010