Showing NP-Card for Tyramine (NP0000398)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:41:48 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
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
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 EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-09View Spectrum
Species
Species of Origin
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