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Showing metabocard for 1-Phenylethylamine (HMDB0002017)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2023-02-21 17:16:03 UTC
HMDB IDHMDB0002017
Secondary Accession Numbers
Metabolite Identification
Common Name1-Phenylethylamine
Description1-Phenylethylamine, also known as a-aminoethylbenzene or a-methylbenzylamine, 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. 1-Phenylethylamine 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 1-phenylethylamine a potential biomarker for the consumption of these foods. 1-Phenylethylamine 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 significant number of articles have been published on 1-Phenylethylamine.
Structure
Data?1676999763
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002017 (1-Phenylethylamine)

  Mrv0541 02231219192D          

  9  9  0  0  0  0            999 V2000
   12.4770   -3.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4770   -4.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1916   -2.9471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1916   -4.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7626   -4.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1916   -5.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7626   -5.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4770   -5.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7625   -2.9470    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
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
  9  1  1  0  0  0  0
M  END
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3D MOL for HMDB0002017 (1-Phenylethylamine)

HMDB0002017
     RDKit          3D
1-Phenylethylamine
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.1480    0.9690    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3646   -0.1455    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8197   -1.3996    0.1390 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0884   -0.0294    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9290   -1.1192    0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2741   -1.0843    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7747    0.1193   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9637    1.2175   -0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6384    1.1413   -0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9824    0.9558   -1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9004    1.9629    0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199    0.7947    0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4313   -0.1212    1.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114   -1.3481   -0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7195   -2.1945    0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -2.0360    0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -1.9387    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8330    0.1382   -0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3990    2.1207   -0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0123    1.9972   -0.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
M  END
Download

3D SDF for HMDB0002017 (1-Phenylethylamine)

  Mrv0541 02231219192D          

  9  9  0  0  0  0            999 V2000
   12.4770   -3.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4770   -4.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1916   -2.9471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1916   -4.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7626   -4.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1916   -5.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7626   -5.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4770   -5.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7625   -2.9470    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
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
  9  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002017

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(N)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3

> <INCHI_KEY>
RQEUFEKYXDPUSK-UHFFFAOYSA-N

> <FORMULA>
C8H11N

> <MOLECULAR_WEIGHT>
121.1796

> <EXACT_MASS>
121.089149357

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
14.193122907132498

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-phenylethan-1-amine

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
1.5155892766666663

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.734673935767288

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
38.9502

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+/-)-α-methylbenzylamine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0002017 (1-Phenylethylamine)

HMDB0002017
     RDKit          3D
1-Phenylethylamine
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.1480    0.9690    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3646   -0.1455    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8197   -1.3996    0.1390 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0884   -0.0294    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9290   -1.1192    0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2741   -1.0843    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7747    0.1193   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9637    1.2175   -0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6384    1.1413   -0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9824    0.9558   -1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9004    1.9629    0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199    0.7947    0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4313   -0.1212    1.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114   -1.3481   -0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7195   -2.1945    0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -2.0360    0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -1.9387    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8330    0.1382   -0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3990    2.1207   -0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0123    1.9972   -0.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
M  END
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PDB for HMDB0002017 (1-Phenylethylamine)

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      23.290  -6.271   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.290  -7.811   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      24.624  -5.501   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      24.624  -8.581   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.957  -8.581   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.624 -10.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.957 -10.121   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.290 -10.891   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.957  -5.501   0.000  0.00  0.00           C+0
CONECT    1    2    3    9                                                  
CONECT    2    1    4    5                                                  
CONECT    3    1                                                            
CONECT    4    2    6                                                       
CONECT    5    2    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0002017 (1-Phenylethylamine)

COMPND    HMDB0002017
HETATM    1  C1  UNL     1      -2.148   0.969   0.071  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.365  -0.145   0.683  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.820  -1.400   0.139  1.00  0.00           N  
HETATM    4  C3  UNL     1       0.088  -0.029   0.351  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.929  -1.119   0.535  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.274  -1.084   0.251  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.775   0.119  -0.241  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.964   1.218  -0.434  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.638   1.141  -0.140  1.00  0.00           C  
HETATM   10  H1  UNL     1      -1.982   0.956  -1.020  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.900   1.963   0.488  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.220   0.795   0.301  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.431  -0.121   1.801  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.711  -1.348  -0.364  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.719  -2.194   0.788  1.00  0.00           H  
HETATM   16  H7  UNL     1       0.480  -2.036   0.924  1.00  0.00           H  
HETATM   17  H8  UNL     1       2.929  -1.939   0.396  1.00  0.00           H  
HETATM   18  H9  UNL     1       3.833   0.138  -0.462  1.00  0.00           H  
HETATM   19  H10 UNL     1       2.399   2.121  -0.815  1.00  0.00           H  
HETATM   20  H11 UNL     1      -0.012   1.997  -0.287  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    4   13
CONECT    3   14   15
CONECT    4    5    5    9
CONECT    5    6   16
CONECT    6    7    7   17
CONECT    7    8   18
CONECT    8    9    9   19
CONECT    9   20
END
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SMILES for HMDB0002017 (1-Phenylethylamine)

CC(N)C1=CC=CC=C1
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INCHI for HMDB0002017 (1-Phenylethylamine)

InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H11N
Average Molecular Weight121.1796
Monoisotopic Molecular Weight121.089149357
IUPAC Name1-phenylethan-1-amine
Traditional Name(+/-)-α-methylbenzylamine
CAS Registry Number98-84-0
SMILES
CC(N)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3
InChI KeyRQEUFEKYXDPUSK-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
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility42 mg/L at 20 °CNot Available
LogP1.49MEYLAN,WM & HOWARD,PH (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.014 +/- 0.0065 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.14 +/- 0.027 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.0070 +/- 0.002 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0071 +/- 0.0045 uMAdult (>18 years old)BothParkinson's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Parkinson's disease
  1. Miura Y: Plasma beta-phenylethylamine in Parkinson's disease. Kurume Med J. 2000;47(4):267-72. [PubMed:11197147 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022799
KNApSAcK IDNot Available
Chemspider ID7130
KEGG Compound IDC02455
BioCyc IDNot Available
BiGG ID45591
Wikipedia Link1-Phenylethylamine
METLIN ID3246
PubChem Compound7408
PDB IDNot Available
ChEBI ID670
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLee, C. C.; Spinks, J. W. T. Rearrangement in the reaction between 2-phenylethylamine-1-C14 and nitrous acid. Canadian Journal of Chemistry (1953), 31 761-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Miura Y: Plasma beta-phenylethylamine in Parkinson's disease. Kurume Med J. 2000;47(4):267-72. [PubMed:11197147 ]
  2. Samonina-Kosicka J, Kanska M: Mechanistic studies of reactions catalysed by diamine oxidase using isotope effects. Isotopes Environ Health Stud. 2013;49(3):357-64. doi: 10.1080/10256016.2013.825612. [PubMed:24117430 ]

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] B
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Enzyme Details
2. Amine oxidase [flavin-containing] A
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Enzyme Details
3. Aromatic-L-amino-acid decarboxylase
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
Enzyme Details
4. Membrane primary amine oxidase
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Enzyme Details
5. Retina-specific copper amine oxidase
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11