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:
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
Related Categories
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.
signalword
Warning
hcodes
pcodes
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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Marc Morant et al.
Plant molecular biology, 63(1), 1-19 (2006-12-13)
A burst of evolutionary duplication upon land colonization seems to have led to the large superfamily of cytochromes P450 in higher plants. Within this superfamily some clans and families are heavily duplicated. Others, such as genes involved in the phenylpropanoid
M A Newman et al.
Molecular plant-microbe interactions : MPMI, 14(6), 785-792 (2001-06-02)
Inoculation of pepper leaves, Capsicum annuum cv. Early Calwonder ECW 10R, with strains of Xanthomonas campestris led to an accumulation of the phenolic conjugates feruloyltyramine (FT) and p-coumaroyltyramine (CT) 24 h postinoculation in nonhost- and gene-for-gene-determined incompatible interactions with X.
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
Effects of typheramide and alfrutamide found in Allium species on cyclooxygenases and lipoxygenases.
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
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
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