Showing Compound Card for Hordenine (CDB000053)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (5) Show 6 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:23:03 UTC
Updated at2020-11-18 16:34:42 UTC
CannabisDB IDCDB000053
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHordenine
DescriptionHordenine 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, a strong basic compound, is a colorless solid that is soluble in organic solvents. Hordenine is biosynthesized by the stepwise N-methylation of tyramine, which is first converted to N-methyltyramine by tyramine N-methyltransferase and then is methylated to hordenine (PMID: 24257763 ). Hordenine exists in all living organisms, ranging from plants to humans. It is found in highest concentrations with barley (Hordeum species), from which its name is derived. Hordenine is also found in cannabis plants (PMID:6991645 ). Several varieties of plants in the family Cactacea (cacti) produce hordenine which, as a potent phenylethylamine alkaloid, has antibacterial and antibiotic properties (PMID: 30609368 ; PMID: 30128579 ). Hordenine has been found in several different foods, such as cereals and cereal products, corns, oats, sweet oranges, and tamarinds making it a potential biomarker for the consumption of these foods. People consuming beer brewed from barley will have higher levels of hordenine. However, hordenine in urine interferes with tests for morphine, heroin and other opioid drugs (PMID: 1618458 ). Hordenine is widely sold as an ingredient of nutritional supplements, with the claims that it is a stimulant of the central nervous system and can promote weight loss by enhancing metabolism.
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 Weight165.23
Monoisotopic Molecular Weight165.1154
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
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 RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHordenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9500000000-acdc91b4203b177fc754Spectrum
Predicted GC-MSHordenine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9310000000-734c4e2c455b97372774Spectrum
Predicted GC-MSHordenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHordenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0a4i-0900000000-a2d459701f761877da822020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-08fr-0900000000-31d50de8a8a2bed634a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-a31932c1e050617567302021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-7837d9fdc06599e5e4772021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ , positivesplash10-0uvo-9900000000-130b6ae804451c70f74f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-00xr-0900000000-25885270de2c1836c33b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-0096-9500000000-8b84d5e79a70fa3d426a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-00dl-8900000000-31b039648b094d1219b12020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 6V, positivesplash10-00xr-0900000000-25885270de2c1836c33b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 3V, positivesplash10-014i-0900000000-af85ba014415bf9af0252020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 4V, positivesplash10-014i-0900000000-35709636b966d858c1472020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 6V, positivesplash10-014i-0900000000-cb918f599a55448f67b12020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 8V, positivesplash10-014i-0900000000-2c71ef92063a1e597ef92020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 9V, positivesplash10-01b9-0900000000-4a5dab8033ea67d49fed2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 11V, positivesplash10-00xr-0900000000-ceea75c15d32fbdad6b12020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 13V, positivesplash10-00di-0900000000-0786df40672ae99b47022020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 14V, positivesplash10-00di-0900000000-739407a14a5e392c93bb2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 16V, positivesplash10-00di-0900000000-ea6d249aa8c9a27346032020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 18V, positivesplash10-00di-0900000000-95ea20554b9c70cfdb042020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 19V, positivesplash10-00di-0900000000-840ccb1e804c5f2bd8592020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 21V, positivesplash10-00di-1900000000-b5bd97221f7577432dff2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 23V, positivesplash10-00di-1900000000-4e1722b74214bbe8fb5d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 24V, positivesplash10-00di-2900000000-ace89f936dcba1a150152020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 26V, positivesplash10-00di-3900000000-1c1e33c685a2bab4ba2e2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 28V, positivesplash10-00dl-4900000000-77c74c5dbd9c018c64f52020-07-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Protein arginine N-methyltransferase 3PRMT311p15.1O60678 details
HemK methyltransferase family member 1HEMK1Q9Y5R4 details
Methyltransferase-like protein 2BMETTL2BQ6P1Q9 details
Methyltransferase-like protein 6METTL6Q8TCB7 details
Uncharacterized methyltransferase WBSCR22WBSCR22O43709 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Protein arginine N-methyltransferase 3PRMT311p15.1O60678 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0004366
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
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Meyer E: Separation of two distinct S-adenosylmethionine dependent N-methyltransferases involved in hordenine biosynthesis in Hordeum vulgare. Plant Cell Rep. 1982 Dec;1(6):236-9. doi: 10.1007/BF00272627. [PubMed:24257763 ]
  3. Zhou JW, Ruan LY, Chen HJ, Luo HZ, Jiang H, Wang JS, Jia AQ: Inhibition of Quorum Sensing and Virulence in Serratia marcescens by Hordenine. J Agric Food Chem. 2019 Jan 23;67(3):784-795. doi: 10.1021/acs.jafc.8b05922. Epub 2019 Jan 14. [PubMed:30609368 ]
  4. Zhou JW, Hou B, Liu GY, Jiang H, Sun B, Wang ZN, Shi RF, Xu Y, Wang R, Jia AQ: Attenuation of Pseudomonas aeruginosa biofilm by hordenine: a combinatorial study with aminoglycoside antibiotics. Appl Microbiol Biotechnol. 2018 Nov;102(22):9745-9758. doi: 10.1007/s00253-018-9315-8. Epub 2018 Aug 20. [PubMed:30128579 ]
  5. 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. doi: 10.1016/0379-0738(92)90076-9. [PubMed:1618458 ]

Enzymes

Enzyme Details
1. Protein arginine N-methyltransferase 3
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
Enzyme Details
2. HemK methyltransferase family member 1
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
Enzyme Details
3. Methyltransferase-like protein 2B
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Molecular weight:
Not Available
Enzyme Details
4. Methyltransferase-like protein 6
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL6
Uniprot ID:
Q8TCB7
Molecular weight:
Not Available
Enzyme Details
5. Uncharacterized methyltransferase WBSCR22
General function:
Not Available
Specific function:
Methyltransferase that may act on DNA.
Gene Name:
WBSCR22
Uniprot ID:
O43709
Molecular weight:
Not Available