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Showing NP-Card for Tyramine (NP0000398)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-09 16:06:27 UTC
NP-MRD IDNP0000398
Secondary Accession NumbersNone
Natural Product Identification
Common NameTyramine
DescriptionTyramine 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. Tyramine is a biomarker for the consumption of cheese
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000398 (Tyramine)


  Mrv1652306232000432D          

 10 10  0  0  0  0            999 V2000
   -2.0087   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7231   -0.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4377   -1.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4377   -2.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -2.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522   -2.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.7820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
Download

3D MOL for NP0000398 (Tyramine)

HMDB0000306
     RDKit          3D
Tyramine
 21 21  0  0  0  0  0  0  0  0999 V2000
    3.5632    0.7281    0.4180 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206    0.7710    0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246   -0.2938   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415   -0.3037   -0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525   -1.0573    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0422   -1.0523    0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746   -0.2739   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569   -0.2606   -0.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0848    0.4803   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6976    0.4720   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649    0.6612   -0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9795   -0.1155    0.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011    1.7670    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.6173    1.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692   -1.2758   -0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -0.1152   -1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0902   -1.6570    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882   -1.6462    1.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6799    0.3961    0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742    1.0933   -1.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1666    1.0649   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
M  END
Download

3D SDF for NP0000398 (Tyramine)


  Mrv1652306232000432D          

 10 10  0  0  0  0            999 V2000
   -2.0087   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7231   -0.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4377   -1.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4377   -2.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -2.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522   -2.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.7820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000398

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C8H11NO

> <MOLECULAR_WEIGHT>
137.179

> <EXACT_MASS>
137.084063979

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.332804080654203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(2-aminoethyl)phenol

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
0.6797131598312175

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.410817992116419

> <JCHEM_PKA_STRONGEST_BASIC>
9.663317955732815

> <JCHEM_POLAR_SURFACE_AREA>
46.25

> <JCHEM_REFRACTIVITY>
41.267300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tyramine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000398 (Tyramine)

HMDB0000306
     RDKit          3D
Tyramine
 21 21  0  0  0  0  0  0  0  0999 V2000
    3.5632    0.7281    0.4180 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206    0.7710    0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246   -0.2938   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415   -0.3037   -0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525   -1.0573    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0422   -1.0523    0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746   -0.2739   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569   -0.2606   -0.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0848    0.4803   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6976    0.4720   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649    0.6612   -0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9795   -0.1155    0.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011    1.7670    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.6173    1.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692   -1.2758   -0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -0.1152   -1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0902   -1.6570    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882   -1.6462    1.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6799    0.3961    0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742    1.0933   -1.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1666    1.0649   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
M  END
Download

PDB for NP0000398 (Tyramine)

HEADER    PROTEIN                                 23-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUN-20         0                                  
HETATM    1  C   UNK     0      -3.750  -2.230   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.083  -1.460   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.417  -2.230   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.417  -3.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.083  -4.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.750  -3.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.751  -4.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.416  -1.460   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.082  -2.230   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.251  -1.460   0.000  0.00  0.00           N+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0000398 (Tyramine)

COMPND    HMDB0000306
HETATM    1  N1  UNL     1       3.563   0.728   0.418  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.121   0.771   0.549  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.525  -0.294  -0.320  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.042  -0.304  -0.231  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.653  -1.057   0.692  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.042  -1.052   0.759  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.775  -0.274  -0.119  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.157  -0.261  -0.063  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.085   0.480  -1.043  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.698   0.472  -1.105  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.865   0.661  -0.589  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.979  -0.116   0.882  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.801   1.767   0.159  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.879   0.617   1.607  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.969  -1.276  -0.026  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.865  -0.115  -1.373  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.090  -1.657   1.369  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.588  -1.646   1.486  1.00  0.00           H  
HETATM   19  H9  UNL     1      -4.680   0.396   0.513  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.674   1.093  -1.734  1.00  0.00           H  
HETATM   21  H11 UNL     1      -0.167   1.065  -1.831  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3   13   14
CONECT    3    4   15   16
CONECT    4    5    5   10
CONECT    5    6   17
CONECT    6    7    7   18
CONECT    7    8    9
CONECT    8   19
CONECT    9   10   10   20
CONECT   10   21
END
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SMILES for NP0000398 (Tyramine)

NCCC1=CC=C(O)C=C1
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INCHI for NP0000398 (Tyramine)

InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
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View in JSmol
Synonyms
ValueSource
2-(p-Hydroxyphenyl)ethylamineChEBI
4-Hydroxy-beta-phenylethylamineChEBI
4-HydroxyphenethylamineChEBI
4-HydroxyphenylethylamineChEBI
beta-(4-Hydroxyphenyl)ethylamineChEBI
p-(2-Aminoethyl)phenolChEBI
p-HydroxyphenethylamineChEBI
p-HydroxyphenylethylamineChEBI
p-TyramineChEBI
TyraminChEBI
4-Hydroxy-b-phenylethylamineGenerator
4-Hydroxy-β-phenylethylamineGenerator
b-(4-Hydroxyphenyl)ethylamineGenerator
Β-(4-hydroxyphenyl)ethylamineGenerator
2-(4'-Hydroxyphenyl)ethylamineHMDB
2-(4-Hydroxyphenyl)ethylamineHMDB
4-(2-Aminoethyl)-phenolHMDB
4-(2-Aminoethyl)-phenol(thyramin)HMDB
4-(2-Aminoethyl)phenolHMDB
4-Hydroxy-benzeneethanamineHMDB
a-(4-Hydroxyphenyl)-b-aminoethaneHMDB
alpha-(4-Hydroxyphenyl)-beta-aminoethaneHMDB
p-(2-Aminoethyl)-phenolHMDB
p-beta-AminoethylphenolHMDB
p-Hydroxy-b-phenethylamineHMDB
p-Hydroxy-b-phenylethylamineHMDB
p-Hydroxy-beta-phenethylamineHMDB
p-Hydroxy-beta-phenylethylamineHMDB
SystogeneHMDB
Tenosin-wirkstoffHMDB
TocosineHMDB
Tyramine baseHMDB
TyrosamineHMDB
UteramineHMDB
Para-tyramineHMDB
4 HydroxyphenethylamineHMDB
2-(4-Hydroxyphenyl)ethanamineHMDB
2-(4’-hydroxyphenyl)ethylamineHMDB
p-Hydroxy-β-phenylethylamineHMDB
p-Β-aminoethylphenolHMDB
Α-(4-hydroxyphenyl)-β-aminoethaneHMDB
Chemical FormulaC8H11NO
Average Mass137.1790 Da
Monoisotopic Mass137.08406 Da
IUPAC Name4-(2-aminoethyl)phenol
Traditional Nametyramine
CAS Registry Number51-67-2
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 KeyDZGWFCGJZKJUFP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-09View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-02-09View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Acacia angustissimaKNApSAcK Database
Acacia greggiiKNApSAcK Database
Acacia rigidula Benth.KNApSAcK Database
Acacia roemerianaKNApSAcK Database
Actaea racemosaKNApSAcK Database
Actinidia chinensisFooDB
Adenocarpus hispanicusKNApSAcK Database
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Allium victorialisKNApSAcK Database
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Antirrhinum majusKNApSAcK Database
Apiaceae-
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Argemone mexicanaKNApSAcK Database
Aristolochia giganteaKNApSAcK Database
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Berberis amurensisKNApSAcK Database
Berberis aquifoliumKNApSAcK Database
Berberis aristataKNApSAcK Database
Berberis thunbergiiKNApSAcK Database
Berberis vulgarisKNApSAcK Database
Berberis wilsoniaeKNApSAcK Database
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bossiaea aquifoliumLOTUS Database
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica olereaceaKNApSAcK Database
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsella bursa-pastorisKNApSAcK Database
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Caulophyllum thalicroidesKNApSAcK Database
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chelidonium majusKNApSAcK Database
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Cissampelos pareiraKNApSAcK Database
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus aurantiumLOTUS Database
Citrus aurantium L. var. amaraKNApSAcK Database
Citrus bergamiaKNApSAcK Database
Citrus latifoliaFooDB
Citrus limonKNApSAcK Database
Citrus maximaFooDB
Citrus medicaKNApSAcK Database
Citrus paradisiFooDB
Citrus reshniLOTUS Database
Citrus reticulataKNApSAcK Database
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clematis parvilobaKNApSAcK Database
Cocculus diversifoliusKNApSAcK Database
Cocculus japonicusKNApSAcK Database
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Coprinopsis atramentariaLOTUS Database
Coptis japonicaKNApSAcK Database
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
Corydalis cavaKNApSAcK Database
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crinum firmifoliumLOTUS Database
Crinum macowaniiLOTUS Database
Crocus sativusFooDB
Ctenodiscus crispatusLOTUS Database
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cyclea barbataKNApSAcK Database
Cyclea peltataKNApSAcK Database
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Cytisus scopariusKNApSAcK Database
Datura innoxiaKNApSAcK Database
Datura inoxiaPlant
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Delphinium pentagynumKNApSAcK Database
Dendrolobium triangulareKNApSAcK Database
Desmodium elegansKNApSAcK Database
Desmodium triflorumKNApSAcK Database
Dicentra spectabilisKNApSAcK Database
Dilphinium caeruleum-
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Erythrina crista-galliKNApSAcK Database
Eschscholzia californicaKNApSAcK Database
Espostoa huanucensisKNApSAcK Database
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Fumaria officinalisKNApSAcK Database
Galanthus trojanusLOTUS Database
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glaucium flavumKNApSAcK Database
Gleditsia triacanthosKNApSAcK Database
Glycine maxKNApSAcK Database
Gnetum montanumKNApSAcK Database
GossypiumFooDB
Grifola frondosaFooDB
Gymnocalycium bodenbenderianumLOTUS Database
Gymnocalycium oenanthemumLOTUS Database
Gymnocalycium reductumLOTUS Database
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareKNApSAcK Database
Hydrastis canadensisKNApSAcK Database
Hypecoum lactiflorumKNApSAcK Database
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lamium barbatumKNApSAcK Database
Lates calcariferLOTUS Database
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Lindera angustifoliaKNApSAcK Database
Linum usitatissimumFooDB
Liparia parvaKNApSAcK Database
Liparia splendensKNApSAcK Database
Litchi chinensisFooDB
Lobivia bachenbergii-
Lobivia binghamiana-
Lobivia pentlandii-
Lolium multiflorumKNApSAcK Database
Lophophora williamsiiKNApSAcK Database
Lotus creticusLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
Lyallia kerguelensisKNApSAcK Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Macleaya cordataKNApSAcK Database
Magnolia obovataKNApSAcK Database
Magnolia officinalisKNApSAcK Database
Mahonia aquifoliumKNApSAcK Database
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Meconopsis cambricaKNApSAcK Database
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Mohonia bealei-
Momordica charantiaFooDB
Monodora junodiiKNApSAcK Database
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Mus musculusLOTUS Database
Musa acuminataKNApSAcK Database
Musa sapientumKNApSAcK Database
Musa x paradisiacaPlant
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Nicotiana tabacumLOTUS Database
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pancratium maritimumLOTUS Database
Pangium eduleFooDB
Panicum miliaceumKNApSAcK Database
Papaver bracteatumKNApSAcK Database
Papaver rhoeasKNApSAcK Database
Papaver somniferumKNApSAcK Database
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pearsonia obovataLOTUS Database
Pediomelum esculentumFooDB
Pereskia aculeataKNApSAcK Database
Perideridia oreganaFooDB
Periplaneta americanaLOTUS Database
Persea americanaKNApSAcK Database
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phellodendron chinensisKNApSAcK Database
Phoebe chekiangensisLOTUS Database
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrumKNApSAcK Database
Piper nigrum L.Plant
Pistacia veraFooDB
Pisum sativumKNApSAcK Database
Plantago majorKNApSAcK Database
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca grandifloraKNApSAcK Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prosopis albaKNApSAcK Database
Prosopis argentinaLOTUS Database
Prosopis glandulosaKNApSAcK Database
Prosopis nigraKNApSAcK Database
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Pseudolobivia kermesina-
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Rhodiola roseaKNApSAcK Database
Rhodiola sachalinensisKNApSAcK Database
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
Romneya coulteriKNApSAcK Database
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salmonella entericaLOTUS Database
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Senegalia berlandieriLOTUS Database
Senegalia roemerianaLOTUS Database
Senna alataKNApSAcK Database
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Silybum marianumKNApSAcK Database
Sinapis albaFooDB
SisymbriumFooDB
Solanum esculentumKNApSAcK Database
Solanum lycopersicumFooDB
Solanum lycopersicum L.KNApSAcK Database
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melanogenaKNApSAcK Database
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumKNApSAcK Database
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaKNApSAcK Database
Stapelia hirsutaKNApSAcK Database
Stephania hernandifoliaKNApSAcK Database
Stephania tetrandraKNApSAcK Database
Stichodactyla giganteaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tephrosia noctifloraKNApSAcK Database
Tetragonia tetragonioidesFooDB
Thalictrum flavumKNApSAcK Database
ThelespermaFooDB
Theobroma cacaoKNApSAcK Database
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tinospora cordifoliaKNApSAcK Database
Tinospora crispaPlant
Tragopogon porrifoliusFooDB
Trichocereus candicansKNApSAcK Database
Trichocereus pachanoiKNApSAcK Database
Trichocereus spachianusKNApSAcK Database
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Turbinicarpus schmiedickeanusLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Vachellia rigidulaLOTUS Database
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Viscum albumKNApSAcK Database
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Xylopia parvifloraKNApSAcK Database
Zantedeschia aethiopicaLOTUS Database
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Zizyphus jujuba var. spinosaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Claviceps purpureaKNApSAcK Database
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point164 - 165 °CNot Available
Boiling Point277.00 to 278.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility10.4 mg/mL at 15 °CNot Available
LogP3.894 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility5.72 g/LALOGPS
logP-0.14ALOGPS
logP0.68ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.41ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.27 m³·mol⁻¹ChemAxon
Polarizability15.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000306
DrugBank IDDB08841
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000433
KNApSAcK IDC00001435
Chemspider ID5408
KEGG Compound IDC00483
BioCyc IDTYRAMINE
BiGG ID35110
Wikipedia LinkTyramine
METLIN ID60
PubChem Compound5610
PDB IDNot Available
ChEBI ID15760
Good Scents IDrw1565911
References
General References
  1. Tyce GM, Stockard J, Sharpless NS, Muenter MD: Excretion of amines and their metabolites by two patients in hepatic coma treated with L-dopa. Clin Pharmacol Ther. 1983 Sep;34(3):390-8. [PubMed:6883916 ]
  2. Jacob G, Costa F, Vincent S, Robertson D, Biaggioni I: Neurovascular dissociation with paradoxical forearm vasodilation during systemic tyramine administration. Circulation. 2003 May 20;107(19):2475-9. Epub 2003 Apr 21. [PubMed:12707242 ]
  3. Nakai T, Yamada R: Basic and clinical reevaluation of tyramine and histamine tests for the investigation of adrenomedullary sympathetic functions. J Clin Endocrinol Metab. 1983 Jul;57(1):19-23. [PubMed:6853676 ]
  4. Jayanthi LD, Balasubramanian N, Balasubramanian AS: Cholinesterases exhibiting aryl acylamidase activity in human amniotic fluid. Clin Chim Acta. 1992 Feb 14;205(3):157-66. [PubMed:1349516 ]
  5. Watson DG, Midgley JM, Chen RN, Huang W, Bain GM, McDonald NM, Reid JL, McGhee CN: Analysis of biogenic amines and their metabolites in biological tissues and fluids by gas chromatography-negative ion chemical ionization mass spectrometry (GC-NICIMS). J Pharm Biomed Anal. 1990;8(8-12):899-904. [PubMed:2100639 ]
  6. Chalon SA, Granier LA, Vandenhende FR, Bieck PR, Bymaster FP, Joliat MJ, Hirth C, Potter WZ: Duloxetine increases serotonin and norepinephrine availability in healthy subjects: a double-blind, controlled study. Neuropsychopharmacology. 2003 Sep;28(9):1685-93. Epub 2003 May 28. [PubMed:12784100 ]
  7. Yin SJ, Lee SC: Tyramine interference in assay of serum dopamine-beta-hydroxylase. Clin Chem. 1977 Mar;23(3):617-8. [PubMed:319927 ]
  8. Andrew R, Watson DG, Best SA, Midgley JM, Wenlong H, Petty RK: The determination of hydroxydopamines and other trace amines in the urine of parkinsonian patients and normal controls. Neurochem Res. 1993 Nov;18(11):1175-7. [PubMed:8255370 ]
  9. Markianos E, Backman H: Diurnal changes in dopamine-beta-hydroxylase, homovanillic acid and 3-methoxy-4-hydroxyphenylglycol in serum of man. J Neural Transm. 1976;39(1-2):79-93. [PubMed:988114 ]
  10. Causon RC, Brown MJ: Measurement of tyramine in human plasma, utilising ion-pair extraction and high-performance liquid chromatography with amperometric detection. J Chromatogr. 1984 Sep 14;310(1):11-7. [PubMed:6501508 ]
  11. Lin J, Cashman JR: Detoxication of tyramine by the flavin-containing monooxygenase: stereoselective formation of the trans oxime. Chem Res Toxicol. 1997 Aug;10(8):842-52. [PubMed:9282832 ]
  12. Wolrath H, Forsum U, Larsson PG, Boren H: Analysis of bacterial vaginosis-related amines in vaginal fluid by gas chromatography and mass spectrometry. J Clin Microbiol. 2001 Nov;39(11):4026-31. [PubMed:11682525 ]
  13. Varma DR, Chemtob S: Endothelium- and beta-2 adrenoceptor-independent relaxation of rat aorta by tyramine and certain other phenylethylamines. J Pharmacol Exp Ther. 1993 Jun;265(3):1096-104. [PubMed:8389852 ]
  14. Gabastou JM, Nugon-Baudon L, Robert Y, Manuel C, Vaissade P, Bourgeon E, Sibeud M, Szylit O, Bourlioux P: [Digestive amines of bacterial origin and behavior disorders. Apropos of a case]. Pathol Biol (Paris). 1996 Apr;44(4):275-81. [PubMed:8763591 ]
  15. Hiroi T, Imaoka S, Funae Y: Dopamine formation from tyramine by CYP2D6. Biochem Biophys Res Commun. 1998 Aug 28;249(3):838-43. [PubMed:9731223 ]
  16. Watson DG, McGhee CN, Midgley JM, Zhou P, Doig WM: Determination of acidic metabolites of biogenic amines in human aqueous humour by gas chromatography--negative ion chemical ionisation mass spectrometry. J Neurochem. 1992 Jan;58(1):116-20. [PubMed:1727423 ]
  17. Antal EJ, Hendershot PE, Batts DH, Sheu WP, Hopkins NK, Donaldson KM: Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine. J Clin Pharmacol. 2001 May;41(5):552-62. [PubMed:11361052 ]
  18. Balbi T, Fusco M, Vasapollo D, Boschetto R, Cocco P, Leon A, Farruggio A: The presence of trace amines in postmortem cerebrospinal fluid in humans. J Forensic Sci. 2005 May;50(3):630-2. [PubMed:15932098 ]
  19. Di Stefano AF, Rusca A: Pressor response to oral tyramine during co-administration with safinamide in healthy volunteers. Naunyn Schmiedebergs Arch Pharmacol. 2011 Dec;384(6):505-15. doi: 10.1007/s00210-011-0674-2. Epub 2011 Aug 19. [PubMed:21850574 ]