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Showing metabocard for N-Methyltyramine (HMDB0003633)

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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
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
Download

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

$$$$
Download

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
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
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
Predicted Chromatographic Properties
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