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Merck
CN

SMB00196

Moupinamide

Synonym(s):

Feruloyltyramine, N-Feruloyltyramine, N-trans-Feruloyltyramine, Alfrutamide

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About This Item

Empirical Formula (Hill Notation):
C18H19NO4
CAS Number:
Molecular Weight:
313.35
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:
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InChI

1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+

SMILES string

COc1cc(\C=C\C(=O)NCCc2ccc(O)cc2)ccc1O

InChI key

NPNNKDMSXVRADT-WEVVVXLNSA-N

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

General description

Natural product derived from plant source.

Biochem/physiol Actions

Moupinamide, also known as N-feruloyltyramine, alfrutamide, is an inhibitor of COX 1 and COX 2 and has potential antioxidant properties.

pictograms

Environment

signalword

Warning

hcodes

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Jae B Park
Journal of medicinal food, 14(3), 226-231 (2011-02-22)
Typheramide (N-caffeoyltyramine) and alfrutamide (N-feruloyltyramine) are phenylpropenoic acid amides found in plants. In this article, typheramide and alfrutamide were isolated from Allium sativum (garlic) and Allium fistulosum (green onion), their chemical structures were confirmed using nuclear magnetic resonance spectroscopic methods
A Schmidt et al.
The Journal of biological chemistry, 274(7), 4273-4280 (1999-02-06)
Hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase (THT; EC 2.3.1.110) catalyzes the transfer of hydroxycinnamic acids from the respective CoA esters to tyramine and other amines in the formation of N-(hydroxycinnamoyl)amines. Expression of THT is induced by Phytophthora infestans, the causative agent of late blight
Peihong Fan et al.
Fitoterapia, 81(2), 124-131 (2009-08-25)
Polygonum sachalinensis is a widespread invasive plant in Europe. Chemical profiles of its different organs were studied by HPLC-UV-ESI/MS. Seven major constituents quercetin-3-O-beta-D-galactopyranoside, quercetin-3-O-arabinopyranoside, lapathoside D, N-trans-feruloyltyramine, lapathoside C, hydropiperoside, and vanicoside B were isolated and identified. The free radical-scavenging
Laura Zacarés et al.
Molecular plant-microbe interactions : MPMI, 20(11), 1439-1448 (2007-11-06)
Inoculation of tomato plants (Solanum lycopersicum cv. Rutgers) with Pseudomonas syringae pv. tomato led to the production of a hypersensitive-like response in this pathovar of tomato. Accumulation of hydroxycinnamic acid amides (HCAA) of tyramine (p-coumaroyltyramine and feruloyltyramine) and dopamine (p-coumaroyldopamine
Mari-Anne Newman et al.
The Plant journal : for cell and molecular biology, 29(4), 487-495 (2002-02-16)
Lipopolysaccharide (LPS) is a ubiquitous component of Gram-negative bacteria which has a number of diverse biological effects on eukaryotic cells. In contrast to the large body of work in mammalian and insect cells, the effects of LPS on plant cells

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