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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 17:39:03 UTC

Update Date

2023-02-21 17:17:01 UTC

HMDB ID

HMDB0004366

Secondary Accession Numbers

HMDB04366

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. Outside of the human body, Hordenine is found, on average, in the highest concentration within barley. Hordenine has also been detected, but not quantified in, several different foods, such as cereals and cereal products, corns, oats, sweet oranges, and tamarinds. This could make hordenine a potential biomarker for the consumption of these foods. In a subsequent paper, Camus reported that the intravenous (IV) administration of some hundreds of mg of hordenine sulfate to dogs or rabbits caused an increase in blood pressure and changes in the rhythm and force of contraction of the heart, noting also that the drug was not orally active. Common salts are hordenine hydrochloride, R-NH3+Cl−, m.p. 178 °C, and hordenine sulfate, (R-NH3+)2SO42−, m.p. 211 °C.The "methyl hordenine HCl" which is listed as an ingredient on the labels of some nutritional supplements is in all likelihood simply hordenine hydrochloride, since the "description" of "methyl hordenine HCl" given by virtually all bulk suppliers of this substance corresponds to that for hordenine hydrochloride (or possibly just hordenine). The hordenine content of various malts and malt fractions was extensively studied by Poocharoen himself, who also provided a good coverage of related literature up to 1983.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

COMPND    HMDB0004366
HETATM    1  C1  UNL     1      -3.520   1.056  -0.377  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.609   0.422   0.527  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.044  -0.838   1.034  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.274   0.441   0.018  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.315  -0.229   0.977  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.076  -0.217   0.460  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.580  -1.233  -0.325  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.869  -1.245  -0.818  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.697  -0.181  -0.507  1.00  0.00           C  
HETATM   10  O1  UNL     1       4.986  -0.215  -1.014  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.230   0.864   0.280  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.933   0.837   0.753  1.00  0.00           C  
HETATM   13  H1  UNL     1      -2.951   1.477  -1.246  1.00  0.00           H  
HETATM   14  H2  UNL     1      -4.321   0.383  -0.704  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.974   1.932   0.162  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.637  -1.715   0.526  1.00  0.00           H  
HETATM   17  H5  UNL     1      -4.166  -0.869   0.922  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.857  -0.972   2.120  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.146   0.044  -0.988  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.954   1.521  -0.024  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.637  -1.274   1.141  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.288   0.306   1.955  1.00  0.00           H  
HETATM   23  H11 UNL     1       0.911  -2.052  -0.552  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.236  -2.074  -1.441  1.00  0.00           H  
HETATM   25  H13 UNL     1       5.667   0.498  -0.854  1.00  0.00           H  
HETATM   26  H14 UNL     1       3.911   1.665   0.492  1.00  0.00           H  
HETATM   27  H15 UNL     1       1.595   1.667   1.366  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4
CONECT    3   16   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7    7   12
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   11
CONECT   10   25
CONECT   11   12   12   26
CONECT   12   27
END

View in JSmol View NMR Assignments View Stereo Labels

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

Not Available

Ingestion (HMDB: HMDB0004366)

Source

Exogenous

Exogenous (HMDB: HMDB0004366)

Food

Food (HMDB: HMDB0004366)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)

Tropical fruit

Tamarind (FooDB: FOOD00180)

Endogenous

Plant

Plant (HMDB: HMDB0004366)
Poaceae (HMDB: HMDB0004366)

Process

Not Available

Role

Industrial application

Drug (HMDB: HMDB0004366)
Vasoconstrictor agent (HMDB: HMDB0004366)

Pharmaceutical industry

Hepatoprotective (HMDB: HMDB0004366)

Agriculture

Pesticide (HMDB: HMDB0004366)

Biological role

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	143.207	30932474
[M+H]+	MetCCS_train_pos	137.808	30932474
[M-H]-	Not Available	143.207	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000307
[M+H]+	Not Available	137.879	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000307

Predicted Molecular 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.056	31661259
DarkChem	[M-H]-	134.896	31661259
DeepCCS	[M+H]+	138.132	30932474
DeepCCS	[M-H]-	134.313	30932474
DeepCCS	[M-2H]-	172.021	30932474
DeepCCS	[M+Na]+	147.559	30932474
AllCCS	[M+H]+	135.6	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	139.7	32859911
AllCCS	[M+Na]+	140.9	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	140.5	32859911
AllCCS	[M+HCOO]-	141.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.5 minutes	32390414
Predicted by Siyang on May 30, 2022	9.1658 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.75 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	153.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	440.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	267.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	107.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	271.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	286.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	835.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	653.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	56.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	829.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	727.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	511.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	73.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hordenine	CN(C)CCC1=CC=C(O)C=C1	2277.5	Standard polar	33892256
Hordenine	CN(C)CCC1=CC=C(O)C=C1	1446.9	Standard non polar	33892256
Hordenine	CN(C)CCC1=CC=C(O)C=C1	1504.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hordenine,1TMS,isomer #1	CN(C)CCC1=CC=C(O[Si](C)(C)C)C=C1	1482.2	Semi standard non polar	33892256
Hordenine,1TBDMS,isomer #1	CN(C)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	1730.7	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

Food Biomarker Ontology

Not Available

VMH ID

C06199

MarkerDB ID

Not Available

Good Scents ID

Not Available

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

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. [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

Reactions

N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteine	details

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

Reactions

N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteine	details

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

Reactions

N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteine	details

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

Reactions

N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteine	details

Showing metabocard for Hordenine (HMDB0004366)

MOL for HMDB0004366 (Hordenine)

3D MOL for HMDB0004366 (Hordenine)

3D SDF for HMDB0004366 (Hordenine)

3D-SDF for HMDB0004366 (Hordenine)

PDB for HMDB0004366 (Hordenine)

3D PDB for HMDB0004366 (Hordenine)

SMILES for HMDB0004366 (Hordenine)

INCHI for HMDB0004366 (Hordenine)

Structure for HMDB0004366 (Hordenine)

3D Structure for HMDB0004366 (Hordenine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions

Reactions