Showing Compound Hordenine (FDB012750)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:20 UTC

Update date

2019-11-26 03:07:31 UTC

Primary ID

FDB012750

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Hordenine

Description

Alkaloid 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 Number

539-15-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4-[2-(Dimethylamino)ethyl]phenol	ChEBI
N,N-Dimethyl-2-(4-hydroxyphenyl)ethylamine	ChEBI
N,N-Dimethyl-4-hydroxy-beta-phenethylamine	ChEBI
N,N-Dimethyltyramine	ChEBI
p-(2-Dimethylaminoethyl)phenol	ChEBI
N,N-Dimethyl-4-hydroxy-b-phenethylamine	Generator
N,N-Dimethyl-4-hydroxy-β-phenethylamine	Generator
Hordenine hydrochloride	HMDB
Hordenine sulfate (2:1)	HMDB
Hordenine sulfate (1:1)	HMDB
4-(2-Dimethylaminoethyl)phenol	HMDB
Anhalin	HMDB
Anhaline	HMDB
Cactine	HMDB
Eremursine	HMDB
Hordenin	HMDB
Hordetin	HMDB
N,N-Dimethyl-p-hydroxyphenethylamine	HMDB
Ordenina	HMDB
Ordenine	HMDB
p-Hydroxy-N,N-dimethylphenethylamine	HMDB
p-[2-(Dimethylamino)ethyl]phenol	HMDB
Peyocactine	HMDB
3595-05-9 (unspecified sulfate)	biospider
4-(2-Dimethylaminoethyl)phenol, 9CI	db_source
4-Hydroxy-N,N-dimethylphenethylamine	db_source
N-Dimethyltyramine	db_source
N,N-Dimethyl-4-hydroxy-β-phenethylamine	biospider
N,n-dimethyl-p-hydroxyphenethylamine	biospider
N,n-dimethyltyramine	biospider
P-hydroxy-n,n-dimethylphenethylamine	biospider
Phenol, 4-[2-(dimethylamino)ethyl]-	biospider
Phenol, p-[2-(dimethylamino)ethyl]-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	29.7 g/L	ALOGPS
logP	1.76	ALOGPS
logP	1.63	ChemAxon
logS	-0.75	ALOGPS
pKa (Strongest Acidic)	10.31	ChemAxon
pKa (Strongest Basic)	9.19	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.34 m³·mol⁻¹	ChemAxon
Polarizability	19.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C10H15NO

IUPAC name

4-[2-(dimethylamino)ethyl]phenol

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

Isomeric SMILES

CN(C)CCC1=CC=C(O)C=C1

Average Molecular Weight

165.2322

Monoisotopic Molecular Weight

165.115364107

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenethylamine alkaloid (CHEBI:5764 )
Tyramine derivatives (C06199 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Poaceae

Role

Industrial application:

Drug

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 72.69%; H 9.15%; N 8.48%; O 9.68%	DFC
Melting Point	Mp 118°	DFC
Boiling Point	Bp11 173-174°	DFC
Experimental Water Solubility	7 mg/mL	MERCK INDEX (1996)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9500000000-acdc91b4203b177fc754	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9310000000-734c4e2c455b97372774	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - QqQ , positive	splash10-0uvo-9900000000-130b6ae804451c70f74f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-00xr-0900000000-25885270de2c1836c33b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-0096-9500000000-8b84d5e79a70fa3d426a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive	splash10-00dl-8900000000-31b039648b094d1219b1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 6V, positive	splash10-00xr-0900000000-25885270de2c1836c33b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 3V, positive	splash10-014i-0900000000-af85ba014415bf9af025	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 4V, positive	splash10-014i-0900000000-35709636b966d858c147	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 6V, positive	splash10-014i-0900000000-cb918f599a55448f67b1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 8V, positive	splash10-014i-0900000000-2c71ef92063a1e597ef9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 9V, positive	splash10-01b9-0900000000-4a5dab8033ea67d49fed	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 11V, positive	splash10-00xr-0900000000-ceea75c15d32fbdad6b1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 13V, positive	splash10-00di-0900000000-0786df40672ae99b4702	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 14V, positive	splash10-00di-0900000000-739407a14a5e392c93bb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 16V, positive	splash10-00di-0900000000-ea6d249aa8c9a2734603	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 18V, positive	splash10-00di-0900000000-95ea20554b9c70cfdb04	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 19V, positive	splash10-00di-0900000000-840ccb1e804c5f2bd859	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 21V, positive	splash10-00di-1900000000-b5bd97221f7577432dff	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 23V, positive	splash10-00di-1900000000-4e1722b74214bbe8fb5d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 24V, positive	splash10-00di-2900000000-ace89f936dcba1a15015	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-2975a2eab163805d1770	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01b9-1900000000-6dd6cd15bdc875928e11	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zor-9500000000-e30fbba1f375c20ecde3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-6597696b538689d6d14c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1900000000-59c23eff8e4369d6798a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9600000000-a54caf3eb3d7672f69bc	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

5764

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04366

CRC / DFC (Dictionary of Food Compounds) ID

HKP28-Z:HKP28-Z

EAFUS ID

Not Available

Dr. Duke ID

HORDENINE

BIGG ID

Not Available

KNApSAcK ID

C00001417

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Hordenine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti diarrheic	55323	Any drug found useful in the symptomatic treatment of diarrhoea.	DUKE
anti feedant			DUKE
broncho elaxant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cardiotonic	38070	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
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
vasoconstrictor	50514	Drug used to cause constriction of the blood vessels.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not 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.

Showing Compound Hordenine (FDB012750)

Structure for FDB012750 (Hordenine)