Showing metabocard for Hordenine (BMDB0004366)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:21 UTC
Update Date2020-04-22 15:13:46 UTC
BMDB IDBMDB0004366
Secondary Accession Numbers
  • BMDB04366
Metabolite Identification
Common NameHordenine
DescriptionHordenine, also known as anhalin or cactine, 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. Hordenine is a very strong basic compound (based on its pKa). Hordenine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 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
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
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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
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
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004366
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 ReferencesNot Available