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Showing NP-Card for Hordenine (NP0044865)

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Record Information
Version2.0
Created at2022-03-10 18:36:50 UTC
Updated at2022-03-10 22:21:13 UTC
NP-MRD IDNP0044865
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044865 (Hordenine)


  Mrv1652303202019002D          

 12 12  0  0  0  0            999 V2000
   32.1429  -15.0835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8575  -10.5460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8575  -11.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1429  -11.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5719  -10.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1429  -10.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1429  -14.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1429  -12.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4285  -13.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8575  -13.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4285  -13.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8575  -13.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  1  0  0  0  0
  8 12  2  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0044865 (Hordenine)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
    3.3081   -0.7818    0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643   -0.1599   -0.6677 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0263    1.2383   -0.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2634   -0.3887   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427    0.3217    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9452    0.1004    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5265   -0.9404    0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8949   -1.1681    0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -0.3597    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0955   -0.5904    0.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1316    0.6970   -0.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    0.9195   -0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8010    0.0301    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5286   -1.2732    1.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438   -1.5665    0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7600    1.7118    0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295    1.3474   -0.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4734    1.6755   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0638   -1.4863   -0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9428   -0.0610   -1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9303    0.0242    1.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7444    1.4276    0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9160   -1.6168    1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657   -2.0009    1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7420   -0.1722    0.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8011    1.3364   -1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3121    1.7359   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
M  END
Download

3D SDF for NP0044865 (Hordenine)


  Mrv1652303202019002D          

 12 12  0  0  0  0            999 V2000
   32.1429  -15.0835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8575  -10.5460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8575  -11.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1429  -11.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5719  -10.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1429  -10.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1429  -14.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1429  -12.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4285  -13.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8575  -13.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4285  -13.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8575  -13.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  1  0  0  0  0
  8 12  2  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044865

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
KUBCEEMXQZUPDQ-UHFFFAOYSA-N

> <FORMULA>
C10H15NO

> <MOLECULAR_WEIGHT>
165.2322

> <EXACT_MASS>
165.115364107

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.353187585007067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[2-(dimethylamino)ethyl]phenol

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
1.6291745590799083

> <ALOGPS_LOGS>
-0.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.308363804255436

> <JCHEM_PKA_STRONGEST_BASIC>
9.187739518335258

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
51.336600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hordenine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0044865 (Hordenine)

Download
PDB for NP0044865 (Hordenine)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0      60.000 -28.156   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      61.334 -19.686   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      61.334 -21.226   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      60.000 -21.996   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      62.668 -18.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      60.000 -18.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      60.000 -26.616   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      60.000 -23.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      58.667 -25.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      61.334 -25.846   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      58.667 -24.306   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      61.334 -24.306   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    3    5    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    8                                                       
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    1    9   10                                                  
CONECT    8    4   11   12                                                  
CONECT    9    7   11                                                       
CONECT   10    7   12                                                       
CONECT   11    8    9                                                       
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0044865 (Hordenine)
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SMILES for NP0044865 (Hordenine)
CN(C)CCC1=CC=C(O)C=C1
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INCHI for NP0044865 (Hordenine)
InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3
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View in JSmol
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 Mass165.2322 Da
Monoisotopic Mass165.11536 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acacia baileyanaPlant
Acacia harpophyllaPlant
Acacia holosericeaPlant
Acacia rigidula Benth.Plant
Acacia spirorbisPlant
Aconitum naviculareLOTUS Database
Aconitum racemulosumLOTUS Database
Aconitum tanguticumLOTUS Database
Alhagi maurorumLOTUS Database
Anomianthus dulcisPlant
Ariocarpus kotschoubeyanusPlant
Ariocarpus retususLOTUS Database
Ariocarpus scapharostrusPlant
Avena sativa L.FooDB
Bongardia chrysogonumLOTUS Database
Boronia inornataLOTUS Database
Cannabis sativaNULL
      Not Available
Citrus aurantiumPlant
Citrus bergamiaPlant
Citrus limonPlant
Citrus medicaPlant
Citrus reshniLOTUS Database
Citrus reticulataPlant
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Corydalis yanhusuoPlant
Cyathobasis fruticulosaLOTUS Database
Dendrolobium triangularePlant
Desmodium elegansPlant
Desmodium multiflorumPlant
Ephedra aphyllaPlant
Eriogonum brevicauleLOTUS Database
Espostoa huanucensisPlant
Flueggea virosaLOTUS Database
Galanthus elewesiiPlant
Galanthus elwesiiLOTUS Database
Galanthus plicatusLOTUS Database
Galanthus plicatus spp.byzantinusPlant
Grateloupia doryphoraLOTUS Database
Greenwayodendron oliveriLOTUS Database
Gymnocalycium bodenbenderianumLOTUS Database
Gymnocalycium bruchiiLOTUS Database
Gymnocalycium reductumLOTUS Database
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
Lobivia bachenbergii-
Lobivia binghamiana-
Lobivia pentlandii-
Mastocarpus stellatus-
Mesembryanthemum variansLOTUS Database
Mimosa ophthalmocentraLOTUS Database
Murraya paniculataLOTUS Database
Pancratium maritimumLOTUS Database
Pancratium trianthumLOTUS Database
Panicum miliaceumPlant
Pereskia aculeataPlant
Phalaris arundinaceaPlant
Phyllophora crispaLOTUS Database
Pseudolobivia kermesina-
Selaginella doederleiniiLOTUS Database
Senecio scandensLOTUS Database
Senegalia berlandieriLOTUS Database
Stapelia giganteaLOTUS Database
Stapelia hirsutaPlant
Tamarindus indicaFooDB
Turbinicarpus alonsoiPlant
Turbinicarpus lophophoroidesLOTUS Database
Uvaria dulcisLOTUS Database
Vachellia rigidulaLOTUS Database
Zanthoxylum culantrilloLOTUS Database
Zea mays L.FooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
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  
Good Scents IDNot Available
References
General References
  1. 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  ] 
  2. 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  ] 
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