Livestock Metabolome Database: Showing metabocard for Tyramine (LMDB00136)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:09 UTC

Update Date

2016-07-20 20:26:56 UTC

Lmdb

LMDB00136

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tyramine

Description

Tyramine is a monoamine compound derived from the amino acid tyrosine. Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish, chocolate, alcoholic beverages, cheese, soy sauce, sauerkraut, and processed meat. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more. Tyramine acts as a neurotransmitter via a G protein-coupled receptor with high affinity for tyramine called TA1. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. An indirect sympathomimetic, Tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase so it prolongs the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals.

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 and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	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

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-2900000000-273503edc6a220e152b6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-2900000000-80980d19fa83d4b86f91	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9700000000-78d2ae48da1eee18358e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9200000000-50c21473a7d48011358c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-1900000000-9b1000a8978b57919c35	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-273503edc6a220e152b6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-80980d19fa83d4b86f91	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-78d2ae48da1eee18358e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-69892c95ab2778a208b3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9600000000-1d5276a762318a00832d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-7900000000-8f3b164f36bc5a4df4d7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-0900000000-066947a256844eb6cbdc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-0900000000-4b0f190d7304f2cec82d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-2feedb2abf4fe5413452	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-052r-0900000000-e67940e0a4f0f1b565c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00lr-9400000000-47a2e802a22167ed8a63	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-3229081a448a277191a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004l-9300000000-e2fc12d41e4c40a9a296	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-92f0b12d0a64443cede8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-001i-9200000000-50c21473a7d48011358c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-d7e9a8705227b4504c5c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-3f02b334907c40a8315c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-e98b3afc6fad78d45d38	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-54239e66d89de3096ca8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0079-0902000000-f09759fc06ef461f3aa5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-9ffe6ee0ce68182216f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-020a5decfb44fc4f97df	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0930000000-32ccc375e75dbab3195c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-51c6cc08017f1672b791	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-1900000000-55c25dd64462c06c5316	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0f96-9500000000-83a70aec6da00b51a6df	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-004i-9100000000-5f044e831c0d2db255fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9000000000-99edae3913507430bf9f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-8944003750ac547c2024	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-00e85becc8cfc59bdb10	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-58e8539844dcdbc977cc	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-053r-9500000000-6deb2b5d214f768ca448	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Colostrum
Meat
Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Ruminal Fluid	Detected and Quantified	24.76 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	98.79 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	166.8 uM	Not Available	Caprine	25471302	details