Showing metabocard for 2-Hydroxyphenethylamine (BMDB0001065)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:38 UTC
Update Date2020-05-11 20:55:23 UTC
BMDB IDBMDB0001065
Secondary Accession Numbers
  • BMDB01065
Metabolite Identification
Common Name2-Hydroxyphenethylamine
Description2-Hydroxyphenethylamine, also known as beta-phenylethanolamine 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. 2-Hydroxyphenethylamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 2-Hydroxyphenethylamine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
Chemical FormulaC8H11NO
Average Molecular Weight137.179
Monoisotopic Molecular Weight137.084063979
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
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Mammary Gland
  • Milk
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001065
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
References
Synthesis ReferenceYe, Qizhuang. Syntheses of conformationally defined analogs of tyramine and phenylethanolamine and their biological evaluations at central dopamine receptors and the active site of phenylethanolamine N-methyltransferase. (1988), 152 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]

Enzymes

Enzyme Details
1. Phenylethanolamine N-methyltransferase
General function:
Involved in phenylethanolamine N-methyltransferase acti
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P10938
Molecular weight:
30918.0