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Showing metabocard for N-Methyltyramine (HMDB0003633)

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enzymes (5) Show 5 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 02:17:17 UTC
Update Date2023-02-21 17:16:45 UTC
HMDB IDHMDB0003633
Secondary Accession Numbers
  • HMDB0060283
  • HMDB0060284
  • HMDB03633
  • HMDB60283
  • HMDB60284
Metabolite Identification
Common NameN-Methyltyramine
DescriptionN-methyltyramine (NMT) is a phenolic amine. NMT is a potent stimulant of gastrin release present in alcoholic beverages produced by alcoholic fermentation, but not by distillation (i.e.: beer.). NMT is well absorbed in the small intestine, especially in the duodenum and jejunum. NMT is metabolized in the liver (the site of first-pass metabolism), but not in the small-intestinal mucosa. NMT is occasionally present in the stools of children and infants. Satisfactory results have been obtained in treating infective shock with injection of natural Fructus Aurantii immaturus (nat-FAI); the anti-shock effective compositions in FAI have been proved to be synephrine and NMT. (PMID: 10772638 , 2570680 ).
Structure
Data?1676999805
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003633 (N-Methyltyramine)


  Mrv0541 02231219462D          

 11 11  0  0  0  0            999 V2000
   17.9186  -15.9176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6332  -11.3801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6332  -12.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9186  -12.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3476  -10.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9186  -15.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9186  -13.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2042  -14.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6332  -14.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2042  -13.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6332  -13.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
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3D MOL for HMDB0003633 (N-Methyltyramine)

HMDB0003633
     RDKit          3D
N-Methyltyramine
 24 24  0  0  0  0  0  0  0  0999 V2000
   -3.1791    1.1543    0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229    0.5592    0.1306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -0.7994    0.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7898   -1.4608   -0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027   -0.7606   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537    0.2200   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829    0.8604   -0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    0.5099    0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056    1.1263    0.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -0.4709    0.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -1.0930    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9036    0.9486    2.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2418    2.2363    0.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1606    0.6802    0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2473    1.1148    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029   -0.8484    1.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126   -1.3756    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6836   -2.5036    0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494   -1.5472   -1.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    0.5348   -1.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3960    1.6334   -1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    1.9404    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2730   -0.7848    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424   -1.8744    1.5895 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
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3D SDF for HMDB0003633 (N-Methyltyramine)


  Mrv0541 02231219462D          

 11 11  0  0  0  0            999 V2000
   17.9186  -15.9176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6332  -11.3801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6332  -12.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9186  -12.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3476  -10.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9186  -15.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9186  -13.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2042  -14.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6332  -14.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2042  -13.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6332  -13.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003633

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO/c1-10-7-6-8-2-4-9(11)5-3-8/h2-5,10-11H,6-7H2,1H3

> <INCHI_KEY>
AXVZFRBSCNEKPQ-UHFFFAOYSA-N

> <FORMULA>
C9H13NO

> <MOLECULAR_WEIGHT>
151.2056

> <EXACT_MASS>
151.099714043

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.417013092088204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[2-(methylamino)ethyl]phenol

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
0.960510916100806

> <ALOGPS_LOGS>
-1.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.5446863243861

> <JCHEM_PKA_STRONGEST_BASIC>
9.824093465521198

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
46.04190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-methyltyramine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0003633 (N-Methyltyramine)

HMDB0003633
     RDKit          3D
N-Methyltyramine
 24 24  0  0  0  0  0  0  0  0999 V2000
   -3.1791    1.1543    0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229    0.5592    0.1306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -0.7994    0.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7898   -1.4608   -0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027   -0.7606   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537    0.2200   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829    0.8604   -0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    0.5099    0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056    1.1263    0.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -0.4709    0.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -1.0930    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9036    0.9486    2.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2418    2.2363    0.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1606    0.6802    0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2473    1.1148    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029   -0.8484    1.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126   -1.3756    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6836   -2.5036    0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494   -1.5472   -1.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    0.5348   -1.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3960    1.6334   -1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    1.9404    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2730   -0.7848    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424   -1.8744    1.5895 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
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PDB for HMDB0003633 (N-Methyltyramine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      33.448 -29.713   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      34.782 -21.243   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      34.782 -22.783   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      33.448 -23.553   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      36.116 -20.473   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.448 -28.173   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.448 -25.093   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.115 -27.403   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.782 -27.403   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.115 -25.863   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.782 -25.863   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    3    5                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    2                                                            
CONECT    6    1    8    9                                                  
CONECT    7    4   10   11                                                  
CONECT    8    6   10                                                       
CONECT    9    6   11                                                       
CONECT   10    7    8                                                       
CONECT   11    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0003633 (N-Methyltyramine)

COMPND    HMDB0003633
HETATM    1  C1  UNL     1      -3.179   1.154   0.928  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.123   0.559   0.131  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.873  -0.799   0.588  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.790  -1.461  -0.203  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.503  -0.761  -0.129  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.854   0.220  -1.018  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.083   0.860  -0.918  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.960   0.510   0.083  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.206   1.126   0.222  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.616  -0.471   0.977  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.391  -1.093   0.859  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.904   0.949   2.002  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.242   2.236   0.816  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.161   0.680   0.722  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.247   1.115   0.366  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.703  -0.848   1.684  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.813  -1.376   0.407  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.684  -2.504   0.209  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.149  -1.547  -1.253  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.187   0.535  -1.835  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.396   1.633  -1.595  1.00  0.00           H  
HETATM   22  H11 UNL     1       4.257   1.940   0.798  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.273  -0.785   1.787  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.142  -1.874   1.590  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6    6   11
CONECT    6    7   20
CONECT    7    8    8   21
CONECT    8    9   10
CONECT    9   22
CONECT   10   11   11   23
CONECT   11   24
END
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SMILES for HMDB0003633 (N-Methyltyramine)

CNCCC1=CC=C(O)C=C1
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INCHI for HMDB0003633 (N-Methyltyramine)

InChI=1S/C9H13NO/c1-10-7-6-8-2-4-9(11)5-3-8/h2-5,10-11H,6-7H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-Hydroxy-N-methylphenethylamineChEBI
Methyl-4-tyramineChEBI
p-(2-Methylaminoethyl)phenolChEBI
4-(2-(Methylamino)ethyl)-phenolHMDB
4-(2-Methylaminoethyl)phenolHMDB
4-[2-(Methylamino)ethyl]-phenolHMDB
4-[2-(Methylamino)ethyl]phenolHMDB
Methyl tyramineHMDB
N-Methyl-p-tyramineHMDB
N-MethyltyraminiumHMDB
NMTHMDB
p-(2-(Methylamino)ethyl)phenolHMDB
p-[2-(Methylamino)ethyl]-phenolHMDB
{p-[2-(methylamino)ethyl]phenol}HMDB
N-MethyltyrosamineHMDB
Methyl-4-tyramine hydrochlorideHMDB
Methyl-4-tyramine hydrobromideHMDB
Chemical FormulaC9H13NO
Average Molecular Weight151.2056
Monoisotopic Molecular Weight151.099714043
IUPAC Name4-[2-(methylamino)ethyl]phenol
Traditional NameN-methyltyramine
CAS Registry Number370-98-9
SMILES
CNCCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H13NO/c1-10-7-6-8-2-4-9(11)5-3-8/h2-5,10-11H,6-7H2,1H3
InChI KeyAXVZFRBSCNEKPQ-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.455Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.4 g/LALOGPS
logP0.48ALOGPS
logP0.96ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)10.54ChemAxon
pKa (Strongest Basic)9.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.04 m³·mol⁻¹ChemAxon
Polarizability17.42 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.20331661259
DarkChem[M-H]-131.0431661259
DeepCCS[M+H]+133.0330932474
DeepCCS[M-H]-129.19930932474
DeepCCS[M-2H]-166.75330932474
DeepCCS[M+Na]+142.26930932474
AllCCS[M+H]+132.932859911
AllCCS[M+H-H2O]+128.432859911
AllCCS[M+NH4]+137.132859911
AllCCS[M+Na]+138.332859911
AllCCS[M-H]-135.232859911
AllCCS[M+Na-2H]-136.732859911
AllCCS[M+HCOO]-138.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.08 minutes32390414
Predicted by Siyang on May 30, 20229.1201 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.0 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid142.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid566.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid283.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid104.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid168.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid72.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid272.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid268.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)710.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid653.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid173.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid774.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid176.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid215.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate621.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA418.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water100.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-MethyltyramineCNCCC1=CC=C(O)C=C12323.2Standard polar33892256
N-MethyltyramineCNCCC1=CC=C(O)C=C11447.4Standard non polar33892256
N-MethyltyramineCNCCC1=CC=C(O)C=C11474.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Methyltyramine,1TMS,isomer #1CNCCC1=CC=C(O[Si](C)(C)C)C=C11473.5Semi standard non polar33892256
N-Methyltyramine,1TMS,isomer #2CN(CCC1=CC=C(O)C=C1)[Si](C)(C)C1666.6Semi standard non polar33892256
N-Methyltyramine,2TMS,isomer #1CN(CCC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1702.1Semi standard non polar33892256
N-Methyltyramine,2TMS,isomer #1CN(CCC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1693.0Standard non polar33892256
N-Methyltyramine,2TMS,isomer #1CN(CCC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1749.5Standard polar33892256
N-Methyltyramine,1TBDMS,isomer #1CNCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11714.0Semi standard non polar33892256
N-Methyltyramine,1TBDMS,isomer #2CN(CCC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C1881.3Semi standard non polar33892256
N-Methyltyramine,2TBDMS,isomer #1CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2183.1Semi standard non polar33892256
N-Methyltyramine,2TBDMS,isomer #1CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2172.1Standard non polar33892256
N-Methyltyramine,2TBDMS,isomer #1CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2040.8Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000435
KNApSAcK IDC00027432
Chemspider ID9345
KEGG Compound IDC02442
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Methyltyramine
METLIN IDNot Available
PubChem Compound9727
PDB IDNot Available
ChEBI ID17458
Food Biomarker OntologyNot Available
VMH IDC02442
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Kimura T, Iwasaki N, Yokoe JI, Haruta S, Yokoo Y, Ogawara KI, Higaki K: Analysis and prediction of absorption profile including hepatic first-pass metabolism of N-methyltyramine, a potent stimulant of gastrin release present in beer, after oral ingestion in rats by gastrointestinal-transit-absorption model. Drug Metab Dispos. 2000 May;28(5):577-81. [PubMed:10772638 ]
  3. Zhao XW, Li JX, Zhu ZR, Sun DQ, Liu SC: Anti-shock effects of synthetic effective compositions of fructus aurantii immaturus. Experimental study and clinical observation. Chin Med J (Engl). 1989 Feb;102(2):91-3. [PubMed:2570680 ]

Enzymes

Enzyme Details
1. Protein arginine N-methyltransferase 3
General function:
Involved in protein methyltransferase activity
Specific function:
Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:
PRMT3
Uniprot ID:
O60678
Molecular weight:
59902.7
Enzyme Details
2. HemK methyltransferase family member 1
General function:
Not Available
Specific function:
N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails
Enzyme Details
3. Methyltransferase-like protein 2B
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails
Enzyme Details
4. Methyltransferase-like protein 6
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL6
Uniprot ID:
Q8TCB7
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails
Enzyme Details
5. Uncharacterized methyltransferase WBSCR22
General function:
Not Available
Specific function:
Methyltransferase that may act on DNA.
Gene Name:
WBSCR22
Uniprot ID:
O43709
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails