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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 17:39:03 UTC
Update Date2019-01-11 19:18:03 UTC
HMDB IDHMDB0004366
Secondary Accession Numbers
  • HMDB04366
Metabolite Identification
Common NameHordenine
DescriptionHordenine 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
Structure
Data?1547234283
Synonyms
ValueSource
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 hydrochlorideMeSH
Hordenine sulfate (2:1)MeSH
Hordenine sulfate (1:1)MeSH
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
Chemical FormulaC10H15NO
Average Molecular Weight165.2322
Monoisotopic Molecular Weight165.115364107
IUPAC Name4-[2-(dimethylamino)ethyl]phenol
Traditional Namehordenine
CAS Registry Number539-15-1
SMILES
CN(C)CCC1=CC=C(O)C=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point117.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7 mg/mLNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9500000000-acdc91b4203b177fc754JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9310000000-734c4e2c455b97372774JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-2975a2eab163805d1770JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-1900000000-6dd6cd15bdc875928e11JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zor-9500000000-e30fbba1f375c20ecde3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-6597696b538689d6d14cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1900000000-59c23eff8e4369d6798aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9600000000-a54caf3eb3d7672f69bcJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012750
KNApSAcK IDC00001417
Chemspider ID61609
KEGG Compound IDC06199
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHordenine
METLIN ID7055
PubChem Compound68313
PDB IDNot Available
ChEBI ID5764
References
Synthesis ReferenceLeete, Edward; Kirkwood, Sam; Marion, Leo. The biogenesis of alkaloids. VI. The formation of hordenine and N-methyltyramine, from tyramine in barley. Canadian Journal of Chemistry (1952), 30 749-60.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Singh AK, Granley K, Misrha U, Naeem K, White T, Jiang Y: Screening and confirmation of drugs in urine: interference of hordenine with the immunoassays and thin layer chromatography methods. Forensic Sci Int. 1992 Apr;54(1):9-22. [PubMed:1618458 ]

Enzymes

General function:
Involved in protein methyltransferase activity
Specific function:
Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:
PRMT3
Uniprot ID:
O60678
Molecular weight:
59902.7
General function:
Not Available
Specific function:
N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL6
Uniprot ID:
Q8TCB7
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Methyltransferase that may act on DNA.
Gene Name:
WBSCR22
Uniprot ID:
O43709
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails