N-ACETYLTYRAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H13NO2
Molecular Weight	179.2157
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NCCC1=CC=C(O)C=C1

InChI

InChIKey=ATDWJOOPFDQZNK-UHFFFAOYSA-N

InChI=1S/C10H13NO2/c1-8(12)11-7-6-9-2-4-10(13)5-3-9/h2-5,13H,6-7H2,1H3,(H,11,12)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20496234 | http://www.aensiweb.com/old/jasr/jasr/2013/996-1003.pdf

N-Acetyltyramine is a tyramine alkaloid, isolated from fungi and actinomyces. It was reported that N-Acetyltyramine had many bioactivities, such as fungitoxic activity against Cladosporium sphaerospermum, antitumor activity against A375 human melanoma cells and K562 human leukemia cells, it is an IL-1R antagonist and inhibitor of factor XIIIa.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cladosporium sphaerospermum 1 Target ID: CHEMBL613345 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20496234	Inhibitor 8297
Interleukin-1 receptor 1 Target ID: CHEMBL1959 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20496234 \| https://www.researchgate.net/publication/292229283_Il-1R_antagonists_from_microorganisms_II_Studies_on_the_metabolite_of_streptomyces_660	Antagonist 2778
Coagulation factor XIII 2 Target ID: CHEMBL4530 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20496234	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Melanoma 88 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20496234	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Analysis of biogenic amine variability among individual fly heads with micellar electrokinetic capillary chromatography-electrochemical detection.	2005 Nov 1	16255588
New chemical constituents from the endophyte Streptomyces species LR4612 cultivated on Maytenus hookeri.	2006 Mar	17193270
[New aspects of biosynthesis and metabolism of N-acyldopamines in rat tissues].	2007 Nov-Dec	18173129
Streptomyces alni sp. nov., a daidzein-producing endophyte isolated from a root of Alnus nepalensis D. Don.	2009 Feb	19196762
An imidazopyridinone and further metabolites from streptomycetes.	2009 Jul	19731603
Gonadotropic effects of dopamine in isolated workers of the primitively eusocial wasp, Polistes chinensis.	2009 May	19198790
Selective nanomolar detection of dopamine using a boron-doped diamond electrode modified with an electropolymerized sulfobutylether-beta-cyclodextrin-doped poly(N-acetyltyramine) and polypyrrole composite film.	2009 May 15	19382752
Alkaloids in marine algae.	2010 Feb 4	20390105
Three new dioxopiperazine metabolites from a marine-derived fungus Aspergillus fumigatus Fres.	2010 Jun	20496234
An unusual stress metabolite induced by CuCl(2) and other constituents from the leaves of Chloranthus anhuiensis.	2010 Jun 25	20518496
Biogenic amines in microdissected brain regions of Drosophila melanogaster measured with micellar electrokinetic capillary chromatography-electrochemical detection.	2010 Sep 15	20738098

Patents

Sample Use Guides

In Vivo Use Guide

Rats: Maximum effective dose used was 20 umol/kg (for the effect on the blood pressure of rats pretreated with chlorisondarnine)

Route of Administration: Intravenous

In Vitro Use Guide

N-Acetyltyramine showed moderate cytotoxicity against K562 cells (IC50 17.4 uM).

Name

Type

Language

N-ACETYLTYRAMINE

Systematic Name

English

N-(4-HYDROXYPHENETHYL)ACETAMIDE

Systematic Name

English

ACETAMIDE, N-(P-HYDROXYPHENETHYL)-

Common Name

English

ACETAMIDE, N-(2-(4-HYDROXYPHENYL)ETHYL)-

Systematic Name

English

N-(2-(4-HYDROXYPHENYL)ETHYL)ACETAMIDE

Systematic Name

English

TYRAMINE, N-ACETYL

Common Name

English

Code System Code Type Description

PUBCHEM

121051