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Showing Compound Hordenine (FDB012750)

Record Information
Version1.0
Creation date2010-04-08 22:10:20 UTC
Update date2019-11-26 03:07:31 UTC
Primary IDFDB012750
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHordenine
DescriptionAlkaloid from Hordeum vulgare (barley) Hordenine (N,N-dimethyl-4-hydroxyphenylethylamine) is a phenylethylamine alkaloid with antibacterial and antibiotic properties. It stimulates the release of norepinephrine in mammals. It is produced in nature by several varieties of plants in the family Cactaceae and by some in Acacia.; Hordenine is a potent phenylethylamine alkaloid with antibacterial and antibiotic properties produced in nature by several varieties of plants in the family Cactacea. The major source of hordenine in humans is beer brewed from barley. Hordenine in urine interferes with tests for morphine, heroin and other opioid drugs. Hordenine is a biomarker for the consumption of beer. Hordenine is found in many foods, some of which are barley, sweet orange, corn, and cereals and cereal products.
CAS Number539-15-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4-[2-(Dimethylamino)ethyl]phenolChEBI
N,N-Dimethyl-2-(4-hydroxyphenyl)ethylamineChEBI
N,N-Dimethyl-4-hydroxy-beta-phenethylamineChEBI
N,N-DimethyltyramineChEBI
p-(2-Dimethylaminoethyl)phenolChEBI
N,N-Dimethyl-4-hydroxy-b-phenethylamineGenerator
N,N-Dimethyl-4-hydroxy-β-phenethylamineGenerator
Hordenine hydrochlorideHMDB
Hordenine sulfate (2:1)HMDB
Hordenine sulfate (1:1)HMDB
4-(2-Dimethylaminoethyl)phenolHMDB
AnhalinHMDB
AnhalineHMDB
CactineHMDB
EremursineHMDB
HordeninHMDB
HordetinHMDB
N,N-Dimethyl-p-hydroxyphenethylamineHMDB
OrdeninaHMDB
OrdenineHMDB
p-Hydroxy-N,N-dimethylphenethylamineHMDB
p-[2-(Dimethylamino)ethyl]phenolHMDB
PeyocactineHMDB
3595-05-9 (unspecified sulfate)biospider
4-(2-Dimethylaminoethyl)phenol, 9CIdb_source
4-Hydroxy-N,N-dimethylphenethylaminedb_source
N-Dimethyltyraminedb_source
N,N-Dimethyl-4-hydroxy-β-phenethylaminebiospider
N,n-dimethyl-p-hydroxyphenethylaminebiospider
N,n-dimethyltyraminebiospider
P-hydroxy-n,n-dimethylphenethylaminebiospider
Phenol, 4-[2-(dimethylamino)ethyl]-biospider
Phenol, p-[2-(dimethylamino)ethyl]-biospider
Predicted Properties
PropertyValueSource
Water Solubility29.7 g/LALOGPS
logP1.76ALOGPS
logP1.63ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)10.31ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.34 m³·mol⁻¹ChemAxon
Polarizability19.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H15NO
IUPAC name4-[2-(dimethylamino)ethyl]phenol
InChI IdentifierInChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3
InChI KeyKUBCEEMXQZUPDQ-UHFFFAOYSA-N
Isomeric SMILESCN(C)CCC1=CC=C(O)C=C1
Average Molecular Weight165.2322
Monoisotopic Molecular Weight165.115364107
Classification
Description belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 72.69%; H 9.15%; N 8.48%; O 9.68%DFC
Melting PointMp 118°DFC
Boiling PointBp11 173-174°DFC
Experimental Water Solubility7 mg/mLMERCK INDEX (1996)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9500000000-acdc91b4203b177fc754JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9310000000-734c4e2c455b97372774JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-2975a2eab163805d1770JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-1900000000-6dd6cd15bdc875928e11JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zor-9500000000-e30fbba1f375c20ecde3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-6597696b538689d6d14cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1900000000-59c23eff8e4369d6798aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9600000000-a54caf3eb3d7672f69bcJSpectraViewer
ChemSpider ID61609
ChEMBL IDCHEMBL505789
KEGG Compound IDC06199
Pubchem Compound ID68313
Pubchem Substance IDNot Available
ChEBI ID5764
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04366
CRC / DFC (Dictionary of Food Compounds) IDHKP28-Z:HKP28-Z
EAFUS IDNot Available
Dr. Duke IDHORDENINE
BIGG IDNot Available
KNApSAcK IDC00001417
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHordenine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti asthmatic49167 A drug used to treat asthma.DUKE
anti diarrheic55323 Any drug found useful in the symptomatic treatment of diarrhoea.DUKE
anti feedantDUKE
broncho elaxant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
vasoconstrictor50514 Drug used to cause constriction of the blood vessels.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.