Bovine Metabolome Database: Showing metabocard for Tyramine (BMDB0000306)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:28:09 UTC

Update Date

2020-05-21 16:28:47 UTC

BMDB ID

BMDB0000306

Secondary Accession Numbers

BMDB00306

Metabolite Identification

Common Name

Tyramine

Description

Tyramine, also known as para-tyramine or systogene, belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Tyramine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Tyramine exists in all living species, ranging from bacteria to humans. Tyramine participates in a number of enzymatic reactions, within cattle. In particular, Tyramine can be biosynthesized from L-tyrosine; which is catalyzed by the enzyme aromatic-L-amino-acid decarboxylase. In addition, Tyramine can be converted into dopamine; which is mediated by the enzyme tyrosinase. In cattle, tyramine is involved in the metabolic pathway called the tyrosine metabolism pathway. Tyramine is a potentially toxic compound. Tyramine has been found to be associated with several diseases known as brunner syndrome, ulcerative colitis, crohn's disease, and eosinophilic esophagitis; also tyramine has been linked to the inborn metabolic disorders including celiac disease.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(p-Hydroxyphenyl)ethylamine	ChEBI
4-Hydroxy-beta-phenylethylamine	ChEBI
4-Hydroxyphenethylamine	ChEBI
4-Hydroxyphenylethylamine	ChEBI
beta-(4-Hydroxyphenyl)ethylamine	ChEBI
p-(2-Aminoethyl)phenol	ChEBI
p-Hydroxyphenethylamine	ChEBI
p-Hydroxyphenylethylamine	ChEBI
p-Tyramine	ChEBI
Tyramin	ChEBI
4-Hydroxy-b-phenylethylamine	Generator
4-Hydroxy-β-phenylethylamine	Generator
b-(4-Hydroxyphenyl)ethylamine	Generator
Β-(4-hydroxyphenyl)ethylamine	Generator
2-(4'-Hydroxyphenyl)ethylamine	HMDB
2-(4-Hydroxyphenyl)ethylamine	HMDB
4-(2-Aminoethyl)-phenol	HMDB
4-(2-Aminoethyl)-phenol(thyramin)	HMDB
4-(2-Aminoethyl)phenol	HMDB
4-Hydroxy-benzeneethanamine	HMDB
a-(4-Hydroxyphenyl)-b-aminoethane	HMDB
alpha-(4-Hydroxyphenyl)-beta-aminoethane	HMDB
p-(2-Aminoethyl)-phenol	HMDB
p-beta-Aminoethylphenol	HMDB
p-Hydroxy-b-phenethylamine	HMDB
p-Hydroxy-b-phenylethylamine	HMDB
p-Hydroxy-beta-phenethylamine	HMDB
p-Hydroxy-beta-phenylethylamine	HMDB
Systogene	HMDB
Tenosin-wirkstoff	HMDB
Tocosine	HMDB
Tyramine base	HMDB
Tyrosamine	HMDB
Uteramine	HMDB
Para-tyramine	HMDB
4 Hydroxyphenethylamine	HMDB
2-(4-Hydroxyphenyl)ethanamine	HMDB
2-(4’-hydroxyphenyl)ethylamine	HMDB
p-Hydroxy-β-phenylethylamine	HMDB
p-Β-aminoethylphenol	HMDB
Α-(4-hydroxyphenyl)-β-aminoethane	HMDB

Chemical Formula

C₈H₁₁NO

Average Molecular Weight

137.179

Monoisotopic Molecular Weight

137.084063979

IUPAC Name

4-(2-aminoethyl)phenol

Traditional Name

tyramine

CAS Registry Number

51-67-2

SMILES

NCCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2

InChI Key

DZGWFCGJZKJUFP-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Phenethylamine
2-arylethylamine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monoamine molecular messenger (CHEBI:15760 )
primary amino compound (CHEBI:15760 )
tyramines (CHEBI:15760 )
Biogenic amines (C00483 )
Tyramine derivatives (C00483 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	164 - 165 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.4 mg/mL at 15 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.14	ALOGPS
logP	0.68	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.41	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.27 m³·mol⁻¹	ChemAxon
Polarizability	15.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adipose Tissue
Adrenal Medulla
Brain
Colostrum
Fibroblasts
Intestine
Liver
Milk
Muscle
Neuron
Placenta
Platelet
Spleen

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tyrosine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Medulla	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29291809	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000306

DrugBank ID

DB08841

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

5610

PDB ID

Not Available

ChEBI ID

15760

References

Synthesis Reference

Wang, Yalou; Xie, Dongmei. Improved synthesis method of tyramine. Zhongguo Yaowu Huaxue Zazhi (1994), 4(2), 128-9.

Material Safety Data Sheet (MSDS)

Not Available

General References

Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

Enzyme Details

1. Membrane primary amine oxidase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity (By similarity).
Gene Name:: AOC3
Uniprot ID:: Q9TTK6
Molecular weight:: 84500.0

Reactions

Tyramine + Water + Oxygen → Homovanillin + Hydrogen peroxide + Ammonia	details

Enzyme Details

2. Tyrosinase

General function:: Involved in copper ion binding
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the initial and rate limiting step in the cascade of reactions leading to melanin production from tyrosine. In addition to hydroxylating tyrosine to DOPA (3,4-dihydroxyphenylalanine), also catalyzes the oxidation of DOPA to DOPA-quinone, and possibly the oxidation of DHI (5,6-dihydroxyindole) to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: Q8MIU0
Molecular weight:: 60304.0

Reactions

Tyramine + Oxygen → Dopamine + Water	details
Tyramine + Oxygen → L-Dopa + Water	details

Enzyme Details

3. Aromatic-L-amino-acid decarboxylase

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P27718
Molecular weight:: 54294.0

Reactions

L-Tyrosine → Tyramine + Carbon dioxide	details

Showing metabocard for Tyramine (BMDB0000306)

Structure for BMDB0000306 (Tyramine)

Enzymes

Reactions

Reactions

Reactions