Bovine Metabolome Database: Showing metabocard for Hordenine (BMDB0004366)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:09:21 UTC

Update Date

2020-04-22 15:13:46 UTC

BMDB ID

BMDB0004366

Secondary Accession Numbers

BMDB04366

Metabolite Identification

Common Name

Hordenine

Description

Hordenine, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₁₀H₁₅NO

Average Molecular Weight

165.2322

Monoisotopic Molecular Weight

165.115364107

IUPAC Name

4-[2-(dimethylamino)ethyl]phenol

Traditional Name

hordenine

CAS Registry Number

539-15-1

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 Key

KUBCEEMXQZUPDQ-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.

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

Status

Expected but not Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	117.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	7 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9500000000-acdc91b4203b177fc754	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9310000000-734c4e2c455b97372774	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0a4i-0900000000-a2d459701f761877da82	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-08fr-0900000000-31d50de8a8a2bed634a1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-a31932c1e05061756730	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-7837d9fdc06599e5e477	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ , positive	splash10-0uvo-9900000000-130b6ae804451c70f74f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-00xr-0900000000-25885270de2c1836c33b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-0096-9500000000-8b84d5e79a70fa3d426a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive	splash10-00dl-8900000000-31b039648b094d1219b1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 6V, positive	splash10-00xr-0900000000-25885270de2c1836c33b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 3V, positive	splash10-014i-0900000000-af85ba014415bf9af025	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 4V, positive	splash10-014i-0900000000-35709636b966d858c147	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 6V, positive	splash10-014i-0900000000-cb918f599a55448f67b1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 8V, positive	splash10-014i-0900000000-2c71ef92063a1e597ef9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 9V, positive	splash10-01b9-0900000000-4a5dab8033ea67d49fed	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 11V, positive	splash10-00xr-0900000000-ceea75c15d32fbdad6b1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 13V, positive	splash10-00di-0900000000-0786df40672ae99b4702	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 14V, positive	splash10-00di-0900000000-739407a14a5e392c93bb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 16V, positive	splash10-00di-0900000000-ea6d249aa8c9a2734603	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 18V, positive	splash10-00di-0900000000-95ea20554b9c70cfdb04	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 19V, positive	splash10-00di-0900000000-840ccb1e804c5f2bd859	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 21V, positive	splash10-00di-1900000000-b5bd97221f7577432dff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 23V, positive	splash10-00di-1900000000-4e1722b74214bbe8fb5d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 24V, positive	splash10-00di-2900000000-ace89f936dcba1a15015	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 26V, positive	splash10-00di-3900000000-1c1e33c685a2bab4ba2e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 28V, positive	splash10-00dl-4900000000-77c74c5dbd9c018c64f5	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0004366

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hordenine

METLIN ID

7055

PubChem Compound

68313

PDB ID

Not Available

ChEBI ID

5764

References

Synthesis Reference

Leete, 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

Not Available

Showing metabocard for Hordenine (BMDB0004366)

Structure for BMDB0004366 (Hordenine)