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Showing metabocard for N-Methylphenylethanolamine (HMDB0001387)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:39 UTC
HMDB IDHMDB0001387
Secondary Accession Numbers
  • HMDB01387
Metabolite Identification
Common NameN-Methylphenylethanolamine
DescriptionN-Methylphenylethanolamine, also known as (+-)-halostachine or MPEOA, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. N-Methylphenylethanolamine exists in all living organisms, ranging from bacteria to humans. N-Methylphenylethanolamine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N-methylphenylethanolamine a potential biomarker for the consumption of these foods. N-Methylphenylethanolamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on N-Methylphenylethanolamine.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001387 (N-Methylphenylethanolamine)

  Mrv0541 02231219062D          

 11 11  0  0  0  0            999 V2000
    0.3266    0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919    0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415    0.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068    0.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3954    1.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565    0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8218    0.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5334    0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
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3D MOL for HMDB0001387 (N-Methylphenylethanolamine)

HMDB0001387
     RDKit          3D
N-Methylphenylethanolamine
 24 24  0  0  0  0  0  0  0  0999 V2000
    3.0070    1.2152   -0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8796    0.6221    0.4610 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995   -0.7149   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -1.3081    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2409   -2.5995    0.0524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8483   -0.5102    0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278   -0.5431   -0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5603    0.2029   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1050    1.0039   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323    1.0503    0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010    0.2959    1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354    0.4799   -0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159    1.9276    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5773    1.7770   -1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276    0.5761    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5534   -0.7720   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4603   -1.3423    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4646   -1.4633    1.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -2.5514   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0129   -1.1674   -1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0025    0.1685   -2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765    1.5886   -0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780    1.6950    1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942    0.3692    2.2170 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  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
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
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3D SDF for HMDB0001387 (N-Methylphenylethanolamine)

  Mrv0541 02231219062D          

 11 11  0  0  0  0            999 V2000
    0.3266    0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919    0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415    0.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068    0.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3954    1.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565    0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8218    0.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5334    0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001387

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCC(O)C1=CC=CC=C1

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

> <INCHI_KEY>
ZCTYHONEGJTYQV-UHFFFAOYSA-N

> <FORMULA>
C9H13NO

> <MOLECULAR_WEIGHT>
151.2056

> <EXACT_MASS>
151.099714043

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.258363129922493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(methylamino)-1-phenylethan-1-ol

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
0.9012597036666667

> <ALOGPS_LOGS>
-0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.121327899503143

> <JCHEM_PKA_STRONGEST_BASIC>
9.434562222633247

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
45.268499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
halostachine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0001387 (N-Methylphenylethanolamine)

HMDB0001387
     RDKit          3D
N-Methylphenylethanolamine
 24 24  0  0  0  0  0  0  0  0999 V2000
    3.0070    1.2152   -0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8796    0.6221    0.4610 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995   -0.7149   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -1.3081    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2409   -2.5995    0.0524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8483   -0.5102    0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278   -0.5431   -0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5603    0.2029   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1050    1.0039   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323    1.0503    0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010    0.2959    1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354    0.4799   -0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159    1.9276    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5773    1.7770   -1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276    0.5761    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5534   -0.7720   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4603   -1.3423    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4646   -1.4633    1.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -2.5514   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0129   -1.1674   -1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0025    0.1685   -2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765    1.5886   -0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780    1.6950    1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942    0.3692    2.2170 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  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
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
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PDB for HMDB0001387 (N-Methylphenylethanolamine)

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  C   UNK     0       0.610   0.077   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.732   0.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.616  -1.463   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.944   0.847   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.066   0.071   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.738   2.381   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.944  -2.239   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.279   0.077   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -3.401   0.828   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.279  -1.463   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.729   0.058   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2                                                            
CONECT    7    3   10                                                       
CONECT    8    4   10                                                       
CONECT    9    5   11                                                       
CONECT   10    7    8                                                       
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0001387 (N-Methylphenylethanolamine)

COMPND    HMDB0001387
HETATM    1  C1  UNL     1       3.007   1.215  -0.262  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.880   0.622   0.461  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.600  -0.715  -0.019  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.376  -1.308   0.599  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.241  -2.599   0.052  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.848  -0.510   0.258  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.428  -0.543  -0.979  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.560   0.203  -1.316  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.105   1.004  -0.342  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.532   1.050   0.913  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.401   0.296   1.227  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.735   0.480  -0.617  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.516   1.928   0.419  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.577   1.777  -1.144  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.128   0.576   1.488  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.553  -0.772  -1.101  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.460  -1.342   0.329  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.465  -1.463   1.689  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.301  -2.551  -0.933  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.013  -1.167  -1.732  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.002   0.168  -2.303  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.976   1.589  -0.579  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.978   1.695   1.676  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.994   0.369   2.217  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15
CONECT    3    4   16   17
CONECT    4    5    6   18
CONECT    5   19
CONECT    6    7    7   11
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   24
END
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SMILES for HMDB0001387 (N-Methylphenylethanolamine)

CNCC(O)C1=CC=CC=C1
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INCHI for HMDB0001387 (N-Methylphenylethanolamine)

InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC9H13NO
Average Molecular Weight151.2056
Monoisotopic Molecular Weight151.099714043
IUPAC Name2-(methylamino)-1-phenylethan-1-ol
Traditional Namehalostachine
CAS Registry Number68579-60-2
SMILES
CNCC(O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3
InChI KeyZCTYHONEGJTYQV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point74 - 76 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022596
KNApSAcK IDNot Available
Chemspider ID889
KEGG Compound IDC03711
BioCyc IDN-METHYLPHENYLETHANOLAMINE
BiGG IDNot Available
Wikipedia LinkHalostachine
METLIN ID6207
PubChem Compound913
PDB IDNot Available
ChEBI ID16913
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSyrneva, Yu. I. The pharmacology of the new alkaloid halostachine. Farmakologiya i Toksikologiya (Moscow) (1941), 4(No. 1), 45-51.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Suzuki O, Oya M, Katsumata Y: Characterization of N-methylphenylethylamine and N-methylphenylethanolamine as substrates for type A and type B monoamine oxidase. Biochem Pharmacol. 1980 Oct 1;29(19):2663-7. [PubMed:6775642 ]

Enzymes

Enzyme Details
1. Phenylethanolamine N-methyltransferase
General function:
Involved in methyltransferase activity
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P11086
Molecular weight:
30854.745
Reactions
S-Adenosylmethionine + 2-Hydroxyphenethylamine → S-Adenosylhomocysteine + N-Methylphenylethanolaminedetails