Showing metabocard for 2-Hydroxyphenethylamine (MMDBc0031991)

Animal
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-18 01:57:47 UTC
Update Date2025-11-05 17:13:01 UTC
Metabolite IDMMDBc0031991
Metabolite Identification
Common Name2-Hydroxyphenethylamine
Description2-Hydroxyphenethylamine is a biogenic amine belonging to the class of phenethylamines. Its chemical structure features a phenethylamine backbone with a hydroxyl group at the 2-position of the aromatic ring, which contributes to its reactivity and biological activity. This compound is involved in various metabolic pathways, including those related to amino acid metabolism and neurotransmitter synthesis. Notably, it has been identified in studies examining the biochemical composition of food products, such as duck meat, where its levels increase with storage time alongside other nitrogen-containing compounds (PMID:31892851 ). Additionally, 2-Hydroxyphenethylamine has been linked to metabolic changes in specific patient populations, showing significantly higher abundance in individuals with APC mutations compared to controls, indicating its potential role in metabolic profiling and disease association (PMID:31892851 ). Overall, 2-Hydroxyphenethylamine serves as an important metabolite in both food chemistry and clinical research contexts.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9ab457d9a0>


  Mrv1652305261923542D          

 10 10  0  0  0  0            999 V2000
   -0.1436    0.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1436    0.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8541   -0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5669    1.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579    1.3151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8541   -1.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -1.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2773    0.9108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1436   -1.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9ab457d9a0>

HMDB0001065
     RDKit          3D
2-Hydroxyphenethylamine
 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.3907    0.0842    0.1847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9869    0.2000    0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1082   -0.2674   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3743   -1.5978   -0.9060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291   -0.0579   -0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980   -0.5986   -1.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6439   -0.4398   -0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042    0.2621    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659    0.7986    1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8031    0.6358    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520    0.6601   -0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9340    0.4448    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7678   -0.3742    1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7219    1.2854    0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3722    0.3747   -1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2674   -2.1837   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -1.1436   -1.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3930   -0.8675   -1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1698    0.3667    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5195    1.3486    1.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052    1.0694    1.4926 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9ab457d9a0>


  Mrv1652305261923542D          

 10 10  0  0  0  0            999 V2000
   -0.1436    0.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1436    0.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8541   -0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5669    1.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579    1.3151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8541   -1.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -1.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2773    0.9108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1436   -1.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031991

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2

> <INCHI_KEY>
ULSIYEODSMZIPX-UHFFFAOYSA-N

> <FORMULA>
C8H11NO

> <MOLECULAR_WEIGHT>
137.179

> <EXACT_MASS>
137.084063979

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.182776421954346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-1-phenylethan-1-ol

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
0.46867930999999985

> <ALOGPS_LOGS>
-0.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.12832574116739

> <JCHEM_PKA_STRONGEST_BASIC>
9.128712325389454

> <JCHEM_POLAR_SURFACE_AREA>
46.25

> <JCHEM_REFRACTIVITY>
40.4939

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β phenylethanolamine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9ab457d9a0>

HMDB0001065
     RDKit          3D
2-Hydroxyphenethylamine
 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.3907    0.0842    0.1847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9869    0.2000    0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1082   -0.2674   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3743   -1.5978   -0.9060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291   -0.0579   -0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980   -0.5986   -1.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6439   -0.4398   -0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042    0.2621    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659    0.7986    1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8031    0.6358    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520    0.6601   -0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9340    0.4448    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7678   -0.3742    1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7219    1.2854    0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3722    0.3747   -1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2674   -2.1837   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -1.1436   -1.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3930   -0.8675   -1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1698    0.3667    0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5195    1.3486    1.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052    1.0694    1.4926 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
M  END
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PDB for #<Metabolite:0x00007f9ab457d9a0>

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.268   0.162   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.268   1.693   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.594  -0.607   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.079  -0.607   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.058   2.462   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.601   2.455   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.594  -2.159   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.079  -2.159   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.384   1.700   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.268  -2.942   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                                                            
CONECT   10    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for #<Metabolite:0x00007f9ab457d9a0>

COMPND    HMDB0001065
HETATM    1  N1  UNL     1      -3.391   0.084   0.185  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.987   0.200   0.540  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.108  -0.267  -0.586  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.374  -1.598  -0.906  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.329  -0.058  -0.279  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.298  -0.599  -1.134  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.644  -0.440  -0.898  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.104   0.262   0.195  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.166   0.799   1.044  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.803   0.636   0.802  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.552   0.660  -0.666  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.934   0.445   0.993  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.768  -0.374   1.434  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.722   1.285   0.708  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.372   0.375  -1.475  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.267  -2.184  -0.143  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.944  -1.144  -1.984  1.00  0.00           H  
HETATM   18  H8  UNL     1       3.393  -0.868  -1.575  1.00  0.00           H  
HETATM   19  H9  UNL     1       4.170   0.367   0.349  1.00  0.00           H  
HETATM   20  H10 UNL     1       2.520   1.349   1.902  1.00  0.00           H  
HETATM   21  H11 UNL     1       0.105   1.069   1.493  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3   13   14
CONECT    3    4    5   15
CONECT    4   16
CONECT    5    6    6   10
CONECT    6    7   17
CONECT    7    8    8   18
CONECT    8    9   19
CONECT    9   10   10   20
CONECT   10   21
END
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SMILES for #<Metabolite:0x00007f9ab457d9a0>

NCC(O)C1=CC=CC=C1
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INCHI for #<Metabolite:0x00007f9ab457d9a0>

InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2
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Synonyms
ValueSource
2-Amino-1-phenylethanolChEBI
2-Hydroxy-2-phenylethylamineChEBI
2-Phenyl-2-hydroxyethylamineChEBI
alpha-(Aminomethyl)benzyl alcoholChEBI
beta-Hydroxy-beta-phenylethylamineChEBI
beta-HydroxyphenethylamineChEBI
beta-PhenethanolamineChEBI
beta-PhenylethanolamineChEBI
BisnorephedrineChEBI
PhenethanolamineChEBI
a-(Aminomethyl)benzyl alcoholGenerator
Α-(aminomethyl)benzyl alcoholGenerator
b-Hydroxy-b-phenylethylamineGenerator
Β-hydroxy-β-phenylethylamineGenerator
b-HydroxyphenethylamineGenerator
Β-hydroxyphenethylamineGenerator
b-PhenethanolamineGenerator
Β-phenethanolamineGenerator
b-PhenylethanolamineGenerator
Β-phenylethanolamineGenerator
2-amino-1-Phenyl-1-ethanolHMDB
2-amino-1-Phenylethanol-1HMDB
beta-Hydroxy-beta-phenyl-ethylamineHMDB
beta-Hydroxy-phenethylamineHMDB
beta-HydroxyphenylethylamineHMDB
DL-beta-Phenyl-beta-hydroxyethylamineHMDB
HydroxyethylamineHMDB
PhenylethanolamineHMDB
beta PhenylethanolamineMeSH, HMDB
2 HydroxyphenethylamineMeSH, HMDB
2 PhenylethanolamineMeSH, HMDB
2-PhenylethanolamineMeSH, HMDB
beta HydroxyphenethylamineMeSH, HMDB
2-HydroxyphenethylamineChEBI
Molecular FormulaC8H11NO
Average Mass137.179
Monoisotopic Mass137.084063979
IUPAC Name2-amino-1-phenylethan-1-ol
Traditional Nameβ phenylethanolamine
CAS Registry NumberNot Available
SMILES
NCC(O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2
InChI KeyULSIYEODSMZIPX-UHFFFAOYSA-N