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Showing NP-Card for 2-Hydroxyphenethylamine (NP0000373)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:52 UTC
NP-MRD IDNP0000373
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Hydroxyphenethylamine
Description2-Hydroxyphenethylamine, also known as beta-phenethanolamine or 2-amino-1-phenylethanol, 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. It is the simplest member of the class of phenylethanolamines that is 2-aminoethanol bearing a phenyl substituent at the 1-position. 2-Hydroxyphenethylamine exists in all living organisms, ranging from bacteria to humans. 2-Hydroxyphenethylamine ia an amine found in the brain. It may be modulator of sympathetic functions. Its derivatives are adrenergic agonists and antagonists.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000373 (2-Hydroxyphenethylamine)


  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 NP0000373 (2-Hydroxyphenethylamine)

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 NP0000373 (2-Hydroxyphenethylamine)


  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>
NP0000373

> <DATABASE_NAME>
NP-MRD

> <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 NP0000373 (2-Hydroxyphenethylamine)

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

PDB for NP0000373 (2-Hydroxyphenethylamine)

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 NP0000373 (2-Hydroxyphenethylamine)

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 NP0000373 (2-Hydroxyphenethylamine)

NCC(O)C1=CC=CC=C1
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INCHI for NP0000373 (2-Hydroxyphenethylamine)

InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2
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View in JSmol
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 PhenylethanolamineHMDB
2 HydroxyphenethylamineHMDB
2 PhenylethanolamineHMDB
2-PhenylethanolamineHMDB
beta HydroxyphenethylamineHMDB
2-HydroxyphenethylamineChEBI
Chemical FormulaC8H11NO
Average Mass137.1790 Da
Monoisotopic Mass137.08406 Da
IUPAC Name2-amino-1-phenylethan-1-ol
Traditional Nameβ phenylethanolamine
CAS Registry Number7568-93-6
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-10View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Citrus limonLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pogostemon cablinLOTUS Database
Pseudo-nitzschia multistriataLOTUS Database
Reseda luteolaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Xanthoselinum alsaticumLOTUS Database
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
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Primary aliphatic amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point56.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility45.8 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility21.4 g/LALOGPS
logP0.31ALOGPS
logP0.47ChemAxon
logS-0.81ALOGPS
pKa (Strongest Acidic)14.13ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.49 m³·mol⁻¹ChemAxon
Polarizability15.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001065
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022404
KNApSAcK IDNot Available
Chemspider ID975
KEGG Compound IDC02735
BioCyc IDPHENYLETHANOLAMINE
BiGG IDNot Available
Wikipedia LinkPhenylethanolamine
METLIN ID59
PubChem Compound1000
PDB IDNot Available
ChEBI ID16343
Good Scents IDNot Available
References
General References
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